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Green synthetic method of thiohypophosphate

A technology of thiophosphinate and synthesis method, which is applied in the fields of chemical instruments and methods, compounds of group 5/15 elements of the periodic table, organic chemistry, etc., can solve problems such as limiting wide application, and achieve the effect of great application value

Active Publication Date: 2019-10-15
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, drawbacks such as the use of toxic phosphinoyl chlorides, strong bases or Lewis acids, complex multi-step reactions, and expensive transition metals limit the widespread application of this method.

Method used

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  • Green synthetic method of thiohypophosphate
  • Green synthetic method of thiohypophosphate
  • Green synthetic method of thiohypophosphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Embodiment 1: Preparation of diphenylthiophosphinic acid-S-phenyl ester (compound number 1)

[0011]

[0012] Add N-phenylthiophthalimide (207mg, 1.0mmol) and diphenylphosphine oxide (202mg, 1.0mmol) into 5mL of water, stir and react at 40°C for 3h, filter, wash with water, and air-dry. 245 mg of diphenylthiophosphinic acid-S-phenyl ester was obtained (yield: 79%).

[0013] 1 H NMR (400MHz, CDCl 3 ):δ7.79-7.72(m,4H),7.55-7.50(m,6H),7.38-7.34(m,2H),7.28-7.22(m,3H);LC / MS(M+1) + = 311.1.

Embodiment 2

[0014] Embodiment 2: Preparation of two (4-methylphenyl) thiophosphinic acid-S-phenyl ester (compound number 2)

[0015]

[0016] Add N-phenylthiophthalimide (207mg, 1.0mmol) and bis(4-methylphenyl)phosphine oxide (230mg, 1.0mmol) into 5mL water, stir at 40°C for 2h, filter, Washed with water and air-dried to obtain 284 mg of bis(4-methylphenyl)thiophosphinic acid-S-phenyl (yield: 84%).

[0017] 1 H NMR (400MHz, CDCl 3 ):δ7.76-7.72(m,4H),7.54-7.49(m,6H),7.27-7.22(m,3H),2.39(s,6H); LC / MS(M+1) + = 339.1.

Embodiment 3

[0018] Example 3: Preparation of two (3,5-dimethylphenyl) thiophosphinic acid-S-phenyl ester (compound number 3)

[0019]

[0020] Add N-phenylthiophthalimide (207mg, 1.0mmol) and bis(3,5-dimethylphenyl)phosphine oxide (258mg, 1.0mmol) into 5mL of water, and stir at 40°C for 2h , filtered, washed with water, and air-dried to obtain 315 mg of bis(3,5-dimethylphenyl)thiophosphinic acid-S-phenyl ester (yield: 86%).

[0021] 1 H NMR (400MHz, CDCl 3 ):δ7.61-7.55(m,6H),7.39-7.36(m,2H),7.27-7.23(m,3H),2.39(s,6H),2.35(s,6H); LC / MS(M +1) + = 367.2.

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Abstract

The invention relates to a green synthetic method of thiohypophosphate as shown in the formula I as show in the specification, wherein R<1> is phenyl, not more than three methyl or three methoxyl or three halogen substituted phenyl, straight-chain or branch-chain alkyl with no more than six carbon atoms, straight-chain or branch-chain alkenyl with no more then six carbon atoms, straight-chain or branch-chain alkynyl with no more than six carbon atoms and a 3 to 8-member aliphatic ring group; R<2> is phenyl, not more than three methyl or three methoxyl or three halogen substituted phenyl, pyridyl, benzyl, naphthyl and a 3 to 8-member aliphatic ring group; according to the synthetic method, thiohypophosphate is a product directly obtained by enabling N-R<2> thiophthalimide to react with di-R<1> based phosphine oxide with water as a solvent.

Description

technical field [0001] The invention relates to a method for synthesizing thiophosphinate. The method only needs to use water as a solvent, does not need to add any catalyst or alkali, and is more environmentally friendly than the methods reported in previous literatures. The obtained thiophosphinate has important applications in the fields of medicine, pesticide, chemical industry and the like. Background technique [0002] With the rapid development of the global economy, environmental issues are getting more and more attention. Green chemistry, aimed at reducing toxic or polluting waste from chemical processes, has received increasing attention over the past few decades (see Anastas, P.; Eghbali, N., Green chemistry: principles and practice. Chemical Society Reviews 2010, 39, 301-312). Generally speaking, the chemical pollution in the reaction system mainly comes from the use of organic solvents and metal catalysts. Therefore, research on environmentally friendly react...

Claims

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Application Information

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IPC IPC(8): C07F9/32C07F9/58
CPCC07F9/3211C07F9/3217C07F9/3223C07F9/3229C07F9/3276C07F9/3282C07F9/3288C07F9/58
Inventor 曾庆乐王光辉周立宏李怒涛
Owner CHENGDU UNIVERSITY OF TECHNOLOGY
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