Method for producing phosphine sulfide compounds
The reaction of phosphine compounds with polysulfide metals at room temperature addresses inefficiencies in existing synthesis methods, enabling efficient production of phosphine sulfide compounds without high-temperature requirements and chromatography purification.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- MITSUI CHEMICALS INC
- Filing Date
- 2024-12-27
- Publication Date
- 2026-07-09
AI Technical Summary
Existing methods for synthesizing phosphine sulfide compounds at room temperature are inefficient, and high-temperature methods are unsuitable due to low thermal stability.
A method involving the reaction of a phosphine compound with a polysulfide metal at room temperature, using sodium or potassium polysulfide as the sulfiding agent, under controlled pH conditions, without column chromatography purification, to produce phosphine sulfide compounds.
The method enables efficient production of phosphine sulfide compounds at room temperature, reducing the need for high-temperature reactions and simplifying the process by eliminating chromatography steps.
Smart Images
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Abstract
Description
Technical Field
[0001] The present disclosure relates to a method for producing a phosphine sulfide compound.
Background Art
[0002] Phosphine sulfide compounds are compounds used in various applications such as nucleic acid pharmaceuticals. As a method for synthesizing a phosphine sulfide compound, a method of synthesizing by reacting a phosphine compound with a sulfurizing agent is known. Sulfur is known as a sulfurizing agent used in the synthesis of phosphine sulfide compounds (see, for example, Non-Patent Document 1).
Prior Art Documents
Non-Patent Documents
[0003]
Non-Patent Document 1
Summary of the Invention
Problems to be Solved by the Invention
[0004] However, in a production method of obtaining a phosphine sulfide compound by reacting a phosphine compound with sulfur as a sulfurizing agent (see, for example, Non-Patent Document 1), the reaction may not proceed sufficiently at room temperature (for example, 15 ° C to 35 ° C; the same applies hereinafter). In this case, it is necessary to raise the reaction temperature, but a synthesis method with a high reaction temperature is not suitable as a method for synthesizing a phosphine sulfide compound with low thermal stability. Therefore, there may be a need for a method for producing a phosphine sulfide compound in which the reaction proceeds easily even at room temperature.
[0005] An object of an embodiment of the present disclosure is to provide a method for producing a phosphine sulfide compound in which the reaction proceeds easily even at room temperature. [Means for solving the problem]
[0006] The means for solving the above problems include the following embodiments. <1> A method for producing a phosphine sulfide compound, comprising the step of reacting a phosphine compound (1) represented by the following formula (1) with a polysulfide metal to obtain a phosphine sulfide compound (2) represented by the following formula (2).
[0007] [ka]
[0008] In equations (1) and (2), R 1 , R 2 , and R 3 Each of these independently represents a hydroxyl group or a monovalent organic group.
[0009] <2> The aforementioned metal polysulfide includes at least one selected from the group consisting of potassium polysulfide and sodium polysulfide. <1> A method for producing the phosphine sulfide compound described above. <3> The molecular weight of the phosphine compound (1) is 1000 or less. <1> or <2> A method for producing the phosphine sulfide compound described above. <4> In the process of obtaining the phosphine sulfide compound (2), The reaction between a phosphine compound and sodium tetrasulfide is carried out under pH conditions of 8.0 or lower. <1> ~ <3> A method for producing a phosphine sulfide compound as described in any one of the above. <5> The process of obtaining the phosphine sulfide compound (2) does not include a step of purification by column chromatography during or after the process. <1> ~ <4> A method for producing a phosphine sulfide compound as described in any one of the above. <6> The step of obtaining the phosphine sulfide compound (2) is as follows: The phosphine compound (1), the aqueous solution of the polysulfide metal, and an organic solvent are mixed, and the phosphine compound (1) and the polysulfide metal are reacted to obtain an aqueous layer and an oil layer containing the phosphine sulfide compound (2). By removing the organic solvent from the oil layer, the phosphine sulfide compound (2) is obtained. including, <1> ~ <5> A method for producing a phosphine sulfide compound as described in any one of the above. [Effects of the Invention]
[0010] According to one embodiment of the present disclosure, a method for producing a phosphine sulfide compound that reacts readily even at room temperature is provided. [Modes for carrying out the invention]
[0011] In this specification, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively. In this specification, the amount of each component in a composition means the total amount of any multiple substances present in the composition, unless otherwise specified. In the numerical ranges described stepwise in this specification, the upper or lower limit stated in one numerical range may be replaced with the upper or lower limit of another numerical range described stepwise, or with the values shown in the examples. In this specification, the term "process" includes not only independent processes but also processes that cannot be clearly distinguished from other processes, provided that their intended purpose is achieved.
[0012] [Method for producing phosphine sulfide compounds] The method for producing a phosphine sulfide compound according to the present disclosure (hereinafter also referred to as the "production method according to the present disclosure") includes a step (hereinafter also referred to as the "reaction step") in which a phosphine compound (1) represented by the following formula (1) is reacted with a polysulfide metal to obtain a phosphine sulfide compound (2) represented by the following formula (2).
[0013] [ka]
[0014] In equations (1) and (2), R 1 , R 2 , and R 3 Each of these independently represents a hydroxyl group or a monovalent organic group.
[0015] As mentioned above, in the manufacturing method for obtaining phosphine sulfide compounds by reacting a phosphine compound with sulfur (elemental) as a sulfidating agent, the reaction sometimes did not proceed sufficiently at room temperature. In the manufacturing method disclosed herein, by using polysulfide metals as the sulfiding agent, the reaction proceeds more easily at room temperature compared to when sulfur (elemental) is used as the sulfiding agent. The reason for this effect is thought to be that the phosphorus (P) in phosphine compound (1) can undergo nucleophilic addition to the disulfide bonds in the polysulfide metal, and the metal atoms in the polysulfide metal do not negatively affect the reaction.
[0016] The manufacturing method described herein will be explained in more detail below.
[0017] <Reaction Process> The manufacturing method of the present disclosure includes a reaction step (i.e., a step of reacting a phosphine compound (1) with a polysulfide metal to obtain a phosphine sulfide compound (2)).
[0018] (Phosphine compound (1)) The phosphine compound (1) is a starting material in the manufacturing method and reaction steps of the present disclosure. Phosphine compound (1) is a compound represented by the following formula (1).
[0019]
Chem.
[0020] In formula (1), R 1 , R 2 , and R 3 each independently represents a hydroxyl group (i.e., -OH group) or a monovalent organic group.
[0021] In formula (1), the organic group represented by R 1 , R 2 , or R 3 includes an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, an alkenyloxy group which may have a substituent, an aryloxy group which may have a substituent, and the like.
[0022] R 1 , R 2 , or R 3 represented organic group may contain a cyclic structure and may contain a heteroatom. Examples of the heteroatom include an oxygen atom and a nitrogen atom.
[0023] R 1 , R 2 , or R 3 The substituent in (i.e., the substituent for an alkyl group or the like) may include a group containing a double bond (e.g., a vinyl group, an allyl group, etc.).
[0024] R 1 , R 2 , or R 3 The carbon number of the represented organic group (e.g., an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, or an aryloxy group) is not particularly limited, but is, for example, 1 to 30, preferably 1 to 20, and more preferably 1 to 10.
[0025] R 1 , R 2, or R 3 Preferably, the organic group represented by is Alkyl alkyl groups having 1 to 30 carbon atoms (more preferably 1 to 20, even more preferably 1 to 10 carbon atoms), Alkenyl groups having 2 to 30 carbon atoms (more preferably 1 to 20, even more preferably 1 to 10 carbon atoms) (particularly preferably vinyl or allyl groups), An aryl group having 6 to 30 carbon atoms (more preferably 1 to 20, even more preferably 1 to 10 carbon atoms) (particularly preferably a phenyl group), Alkoxy groups having 1 to 30 carbon atoms (more preferably 1 to 20, even more preferably 1 to 10), Alkenyloxy groups having 2 to 30 carbon atoms (more preferably 1 to 20, even more preferably 1 to 10) (particularly preferably vinyloxy or allyloxy groups), An aryloxy group having 6 to 30 carbon atoms (more preferably 1 to 20, even more preferably 1 to 10 carbon atoms) (particularly preferably a phenoxy group), These are some examples. R 1 , R 2 , or R 3 The organic group represented by may include a base structure (for example, nucleic acid bases such as adenine, cytosine, guanine, thymine, and uracil).
[0026] There are no particular restrictions on the molecular weight of the phosphine compound (1). The phosphine compound (1) may be a low-molecular-weight compound or a high-molecular-weight compound (e.g., nucleic acid). The molecular weight of the phosphine compound (1) in the form of a low molecular weight compound is preferably 1000 or less, more preferably 700 or less, and even more preferably 500 or less.
[0027] (Phosphine sulfide compound (2)) The phosphine sulfide compound (2) is the target substance in the manufacturing method and reaction steps of this disclosure. The phosphine sulfide compound (2) is a compound represented by the following formula (2).
[0028] [ka]
[0029] In formula (2), R 1 , R 2 , and R 3 Each of these independently represents a hydroxyl group or a monovalent organic group.
[0030] In formula (2), R 1 , R 2 , and R 3 These are, respectively, R in equation (1). 1 , R 2 , and R 3 This is synonymous with the same as the preferred configuration.
[0031] There are no particular restrictions on the molecular weight of the phosphine sulfide compound (2). The phosphine sulfide compound (2) may be a low molecular weight compound or a high molecular weight compound (e.g., nucleic acid). The molecular weight of the phosphine sulfide compound (2) in the form of a low molecular weight compound is preferably 1000 or less, more preferably 700 or less, and even more preferably 500 or less.
[0032] The phosphine sulfide compound (2) may also be a nucleic acid (e.g., an antisense nucleic acid drug). In other words, the reaction in the manufacturing method of this disclosure may be a phosphorothioate reaction in nucleic acids (e.g., antisense nucleic acid drugs). For antisense nucleic acid drugs, see, for example, the Fujifilm Wako Pure Chemical Industries website, "[Series] Basic Course on Nucleic Acid Drug Synthesis, Part 4: Capping and Oxidation / Sulfurization Reactions in Oligonucleotide Synthesis."<https: / / labchem-wako.fujifilm.com / jp / siyaku-blog / 018554.html> You can refer to this. This website describes antisense nucleic acid drugs with the following structure.
[0033] [ka]
[0034] (metal polysulfide) The polysulfide metals function as sulfiding agents in the manufacturing method and reaction steps of the present disclosure. Metallic polysulfides are compounds that contain both disulfide bonds and metal atoms. The number of sulfur atoms (S) contained in the polysulfide metal is preferably 2 to 5. The metal atoms contained in the metal polysulfide are preferably alkali metals, and more preferably sodium or potassium. In other words, the metal polysulfide is preferably an alkali metal polysulfide, and more preferably sodium polysulfide or potassium polysulfide.
[0035] In the reaction process, one type of polysulfide metal may be used, or two or more types may be used. The metal polysulfide in the reaction step preferably includes at least one selected from the group consisting of potassium polysulfide (preferably K2S4) and sodium polysulfide (preferably Na2S4).
[0036] Furthermore, in the reaction process, a combination of a polysulfide metal as a sulfiding agent and a sulfiding agent other than a polysulfide metal (for example, sulfur) may be used.
[0037] (pH) There are no particular restrictions on the pH conditions when reacting the phosphine compound with sodium tetrasulfide in the reaction process. From the viewpoint of promoting the reaction further, the reaction between the phosphine compound and sodium tetrasulfide may be carried out under pH conditions of, for example, 12.0 or less, but is preferably carried out under pH conditions of 11.0 or less, and more preferably under pH conditions of 8.0 or less (even more preferably 1.0 to 8.0, even more preferably 2.0 to 7.5, and even more preferably 3.0 to 7.0).
[0038] pH adjustment can be performed using acids such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, acetic acid, formic acid, carbonic acid, oxalic acid, and benzoic acid.
[0039] (Reaction temperature) In the reaction process, there are no particular restrictions on the reaction temperature when the phosphine compound reacts with sodium tetrasulfide, but it is typically between 15°C and 35°C. As mentioned above, by using polysulfide metals as sulfiding agents in the reaction process, the reaction can be carried out effectively even at room temperature (for example, 15°C to 35°C).
[0040] (Reaction time) There are no particular restrictions on the reaction time when the phosphine compound reacts with sodium tetrasulfide during the reaction process. The reaction time is, for example, 10 seconds or more, preferably 20 seconds or more. The reaction time is, for example, 10 minutes or less, preferably 3 minutes or less, and even more preferably 1 minute or less.
[0041] The manufacturing method of this disclosure preferably does not include a step of purification by column chromatography during or after the reaction step described above. This makes the manufacturing process simpler.
[0042] The manufacturing method of this disclosure uses polysulfide metals as sulfiding agents, which results in easily removable by-products (e.g., H2S). Therefore, the manufacturing method of this disclosure does not require purification by column chromatography during or after the reaction process described above. In contrast, when using sulfiding agents other than polysulfide metals (for example, Beaucage reagent, DDTT, 5-Phenyl-3H-1,2,4-dithiazol-3-one, PADS; all manufactured by Fujifilm Wako Pure Chemical Industries), by-products that are not easily removed may be produced, requiring a purification step by column chromatography. Furthermore, the polysulfide metals used as sulfiding agents in this disclosure have the advantage of being less expensive compared to the other sulfiding agents exemplified above.
[0043] (Preferred embodiment) A preferred reaction step is: The method involves mixing a phosphine compound (1), an aqueous solution of a polysulfide metal, and an organic solvent, and reacting the phosphine compound (1) with the polysulfide metal to obtain an aqueous layer and an oil layer containing a phosphine sulfide compound (2). By removing the organic solvent from the oil layer, a phosphine sulfide compound (2) can be obtained. Includes. According to this preferred embodiment, the phosphine sulfide compound (2) can be obtained by a simple method.
[0044] Examples of organic solvents in the above preferred embodiment include acetonitrile, dichloromethane, ethyl acetate, chloroform, acetone, tetrahydrofuran, methanol, and the like. [Examples]
[0045] The following are examples of the embodiments of this disclosure, but this disclosure is not limited to these embodiments. In the following, "%" refers to "mass%" unless otherwise specified.
[0046] [Example 1] (Triphenyl phosphite was used as phosphine compound (1)) 0.63 g (2.0 mmol) of triphenyl phosphite as phosphine compound (1), 2.0 mL of acetonitrile, and 1.24 g (0.71 mmol) of 10% sodium tetrasulfide (Na2S4) aqueous solution as a polysulfide metal aqueous solution were placed in a 20 mL test tube. The resulting mixture was stirred at 25°C, and a 10% hydrochloric acid aqueous solution was added to the stirring mixture to adjust the pH to 6.9. After 30 seconds, stirring was stopped, and after the oil layer and water layer separated, the oil layer was recovered. The solvent in the oil layer was removed by vacuum distillation, followed by vacuum drying to obtain triphenylphosphorothioate as phosphine sulfide compound (2) as a white solid (yield 94%, 0.67 g). The yield was calculated using the purity determined by HPLC analysis. The conditions for the HPLC analysis are as follows.
[0047] -Conditions for HPLC analysis- Equipment name: Shimadzu HPLC-20 Column: Waters Xbridge C18 3.5μm Mobile phase: 0.1M triethylamine acetate aqueous solution:acetonitrile = 50 vol%:50 vol% Detection wavelength: 260nm Flow rate: 1.5mL / min
[0048] The following shows the NMR analysis results of the obtained white solid. 1 H-NMR (500MHz, CDCl3): δ7.22-7.25(m, 9H), 7.35-7.40(m, 6H) 31 P-NMR (500MHz, CDCl3): δ55.07
[0049] Here, triphenyl phosphite is represented by R in formula (1). 1 , R 2 , and R 3 However, all of them are compounds with a phenoxy group, and triphenylphosphorothioate is, in formula (1), R 1 , R 2 , and R 3 However, all of them are compounds containing a phenoxy group.
[0050] [Comparative Example 1] (Triphenyl phosphite is used as the phosphine compound (1) (when sulfur is used as the sulfurizing agent)) 0.78 g (2.5 mmol) of triphenyl phosphite as phosphine compound (1) and 2.5 mL of acetonitrile were placed in a 20 mL test tube. The resulting mixture was stirred at 25°C, and 0.08 g (2.5 mmol) of sulfur was added to the mixture while it was stirring. After 30 seconds, stirring was stopped, and the composition of the resulting reaction solution was confirmed by HPLC analysis under the same conditions as in Example 1, but the target product was not obtained. Subsequently, stirring was continued for 24 hours, but the target product was still not obtained.
[0051] [Example 2] (Triphenylphosphine used as phosphine compound (1)) 0.53 g (2.0 mmol) of triphenylphosphine as phosphine compound (1), 2.0 mL of methylene chloride, and 1.24 g (0.71 mmol) of 10% sodium tetrasulfide aqueous solution as polymetallic acid aqueous solution were placed in a 20 mL test tube. The resulting mixture was stirred at 25°C, and a 10% hydrochloric acid aqueous solution was added to the stirring mixture to adjust the pH to 6.9. After 30 seconds, stirring was stopped, and after the oil layer and water layer separated, the oil layer was recovered. The solvent in the oil layer was removed by vacuum distillation, followed by vacuum drying to obtain triphenylphosphine sulfide as phosphine sulfide compound (2) as a white solid (yield 96%, 0.57 g). The yield was calculated using the purity determined by HPCL analysis under the same conditions as in Example 1.
[0052] The following shows the NMR analysis results of the obtained white solid. 1 H-NMR (500MHz, CDCl3): δ7.43-7.47(m, 6H), 7.50-7.54(m, 3H), 7.69-7.75(m, 6H) 31 P-NMR (500MHz, CDCl3): δ45.33
[0053] Here, triphenylphosphine is represented by R in formula (1). 1 , R 2 , and R 3 However, all of them are compounds with a phenyl group, and triphenylphosphine sulfide is, in formula (1), R 1 , R 2 , and R 3 However, all of them are compounds containing a phenyl group.
[0054] [Example 3] (Tri-n-octylphosphine used as phosphine compound (1)) 0.69 g (1.75 mmol, 93% purity) of tri-n-octylphosphine as phosphine compound (1), 2.0 mL of methylene chloride, and 1.10 g (0.63 mmol) of 10% sodium tetrasulfide aqueous solution as a polysulfide metal aqueous solution were placed in a 20 mL test tube. The resulting mixture was stirred at 25°C, and a 10% hydrochloric acid aqueous solution was added to the stirring mixture to adjust the pH to 6.9. After 30 seconds, stirring was stopped, and after the oil layer and water layer separated, the oil layer was recovered. The solvent in the oil layer was removed by vacuum distillation, followed by vacuum drying to obtain tri-n-octylphosphine sulfide as phosphine sulfide compound (2) as a colorless, transparent liquid (yield 99%, 0.78 g). The yield was calculated using the purity determined by HPCL analysis under the same conditions as in Example 1.
[0055] The following shows the NMR analysis results of the obtained colorless, transparent liquid. 1 H-NMR (500MHz, CDCl3): δ0.88(t, 9H), 1.22-1.35(m, 24H), 1.35-1.43(m, 6H), 1.54-1.62(m, 6H), 1.75-1.83(m, 6H) 31 P-NMR (500MHz, CDCl3): δ50.67
[0056] Here, tri-n-octylphosphine is R in equation (1). 1 , R 2 , and R 3 However, all of these are compounds with an n-octyl group, and tri-n-octylphosphine sulfide is, in formula (1), R 1 , R 2 , and R 3 However, all of these are compounds with an n-octyl group.
[0057] [Example 4] (Triethyl phosphite was used as phosphine compound (1)) 0.34 g (2.0 mmol) of triethyl phosphite as phosphine compound (1), 2.0 mL of acetonitrile, and 1.24 g (0.71 mmol) of 10% sodium tetrasulfide aqueous solution as a polysulfide metal aqueous solution were placed in a 20 mL test tube. The resulting mixture was stirred at 25°C, and a 10% hydrochloric acid aqueous solution was added to the stirring mixture to adjust the pH to 6.9. After 30 seconds, stirring was stopped, and after the oil layer and water layer separated, the oil layer was recovered. The solvent in the oil layer was removed by vacuum distillation, followed by vacuum drying to obtain triethyl phosphorothioate as phosphine sulfide compound (2) as a colorless, transparent liquid (yield 92%, 0.37 g). The yield was calculated using the purity determined by HPCL analysis under the same conditions as in Example 1.
[0058] The following shows the NMR analysis results of the obtained colorless, transparent liquid. 1 H-NMR(500MHz,CDCl3): δ1.35(t, 9H),4.08-4.22 (m,6H), 31 P-NMR (500MHz, CDCl3): δ69.58
[0059] Here, triethyl phosphite is R in formula (1). 1 , R 2 , and R 3 However, all of them are compounds with an ethoxy group, and triethyl phosphorothioate is, in formula (1), R 1 , R 2 , and R 3 However, all of these are compounds that contain an ethoxy group.
[0060] [Example 5] (Trial phosphite was used as phosphine compound (1)) 0.40 g (1.85 mmol, 94% purity) of trialyl phosphite as phosphine compound (1), 2.0 mL of acetonitrile, and 1.16 g (0.67 mmol) of 10% sodium tetrasulfide aqueous solution as a polysulfide metal aqueous solution were placed in a 20 mL test tube. The resulting mixture was stirred at 25°C, and a 10% hydrochloric acid aqueous solution was added to the stirring mixture to adjust the pH to 6.9. After 30 seconds, stirring was stopped, and after the oil layer and water layer separated, the oil layer was recovered. The solvent in the oil layer was removed by vacuum distillation, followed by vacuum drying to obtain triallyl phosphorothioate as phosphine sulfide compound (2) as a colorless, transparent liquid (yield 98%, 0.42 g). The yield was calculated using the purity determined by HPCL analysis under the same conditions as in Example 1.
[0061] The following shows the NMR analysis results of the obtained colorless, transparent liquid. 1 H-NMR (500MHz, CDCl3): δ4.54-4.61(m, 6H), 5.22-5.28(m, 3H), 5.33-5.41(m, 3H), 5.89-6.00(m, 1H) 31 P-NMR (500MHz, CDCl3): δ70.54
[0062] Here, in formula (1), triallyl phosphite is R 1 , R 2 , and R 3 However, all of them are compounds with an allyloxy group, and triethyl phosphorothioate is, in formula (1), R 1 , R 2 , and R 3 However, all of them are compounds containing an allyloxy group.
[0063] [Example 6] (Triphenyl phosphite was used as phosphine compound (1), pH 1.5) The procedure was the same as in Example 1, except that the amount of 10% hydrochloric acid aqueous solution added was changed and the pH of the mixture during stirring was changed to 1.5. As a result, triphenylphosphorothioate, as the phosphine sulfide compound (2), was obtained as a white solid in a yield of 53%. The yield was calculated using the purity obtained by HPCL analysis under the same conditions as in Example 1.
[0064] [Example 7] (Triphenyl phosphite was used as phosphine compound (1), pH 10.2) The procedure was the same as in Example 1, except that the amount of 10% hydrochloric acid aqueous solution added was changed and the pH of the mixture during stirring was changed to 10.2. As a result, triphenylphosphorothioate, as the phosphine sulfide compound (2), was obtained as a white solid in a yield of 45%. The yield was calculated using the purity obtained by HPCL analysis under the same conditions as in Example 1.
[0065] [Comparative Example 2] The procedure was the same as in Example 4, except that 1.24 g (0.71 mmol) of 10% sodium tetrasulfide aqueous solution, used as the polysulfide metal aqueous solution, was replaced with 0.06 g (2.0 mmol) of sulfur. As a result, although triethyl phosphorothioate was obtained, similar to Example 4, the yield in Comparative Example 2 was 35%, which was lower than the yield in Example 4 (92%).
[0066] [Comparative Example 3] The procedure was the same as in Example 5, except that 1.16 g (0.67 mmol) of 10% sodium tetrasulfide aqueous solution, used as the polysulfide metal aqueous solution, was replaced with 0.06 g (2.0 mmol) of sulfur. As a result, although triallyl phosphorothioate was obtained, similar to Example 5, the yield in Comparative Example 3 was 27%, which was lower than the yield in Example 5 (98%).
Claims
1. A method for producing a phosphine sulfide compound, comprising the step of reacting a phosphine compound (1) represented by the following formula (1) with a metal polysulfide to obtain a phosphine sulfide compound (2) represented by the following formula (2). 【Chemistry 1】 [In equations (1) and (2), R １ , R ２ , and R ３ Each of these independently represents a hydroxyl group or a monovalent organic group.
2. The method for producing a phosphine sulfide compound according to claim 1, wherein the polysulfide metal comprises at least one selected from the group consisting of potassium polysulfide and sodium polysulfide.
3. A method for producing a phosphine sulfide compound according to claim 1, wherein the molecular weight of the phosphine compound (1) is 1000 or less.
4. In the process of obtaining the phosphine sulfide compound (2), A method for producing a phosphine sulfide compound according to claim 1, wherein the reaction between the phosphine compound and sodium tetrasulfide is carried out under pH conditions of 8.0 or less.
5. A method for producing a phosphine sulfide compound according to claim 1, wherein the step of purifying by column chromatography is not included during and after the step of obtaining the phosphine sulfide compound (2).
6. The step of obtaining the phosphine sulfide compound (2) is as follows: The phosphine compound (1), the aqueous solution of the polysulfide metal, and an organic solvent are mixed, and the phosphine compound (1) and the polysulfide metal are reacted to obtain an aqueous layer and an oil layer containing the phosphine sulfide compound (2). By removing the organic solvent from the oil layer, the phosphine sulfide compound (2) is obtained. including, A method for producing a phosphine sulfide compound according to claim 1.