Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

P-nitrophenyl phosphate disodium and preparation method thereof

A technology of disodium nitrophenyl phosphate and nitrophenyl phosphate, applied in the field of disodium p-nitrophenyl phosphate and its preparation, can solve the problems of unsuitable for industrial production, expensive dibenzyl phosphite, carbon tetrachloride Toxicity and other problems, to achieve good application prospects, reduce the difficulty of purification, the effect of thorough hydrolysis

Inactive Publication Date: 2019-12-31
安徽昊帆生物有限公司
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The carbon tetrachloride used in this method is relatively poisonous, and dibenzyl phosphite is also very expensive
In addition, the reaction time is relatively long, and the intermediate is an oil, which requires column purification before hydrogenation, making this method unsuitable for industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • P-nitrophenyl phosphate disodium and preparation method thereof
  • P-nitrophenyl phosphate disodium and preparation method thereof
  • P-nitrophenyl phosphate disodium and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0036] The preparation method of disodium p-nitrophenyl phosphate according to the embodiment of the present invention comprises the following steps:

[0037] Step 1: react p-nitrophenol with dialkyl chlorophosphate in the presence of alkali to obtain O, O-dialkyl p-nitrophenyl phosphate.

[0038] Its reaction formula is shown in following formula (1):

[0039]

[0040] Wherein, the dialkyl chlorophosphate is preferably selected from dimethyl chlorophosphate, diethyl chlorophosphate, diisopropyl chlorophosphate, or a mixture thereof. In other words, the aforementioned R is preferably methyl, ethyl, or propyl.

[0041] The reaction is preferably carried out at 0-25°C, and the reaction time is preferably 4-10 hours.

[0042] Wherein, the base is an inorganic base and / or an organic base, and the inorganic base is selected from sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium hydride, potassium hydride, or a mixture thereof, and the org...

Embodiment 1

[0063] (1) Synthesis of O, O-diethyl-p-nitrophenyl phosphate

[0064] Suspend p-nitrophenol (139 g, 1.0 mol) in dichloromethane and cool to . After quickly dropping triethylamine (121.4g, 1.2mol) into the reaction flask, continue to maintain 0°C and slowly add diethyl chlorophosphate (207g, 1.2mol) dropwise, and then naturally rise to room temperature after dropping, and continue to react for 4h , liquid phase monitoring p-nitrophenol is almost consumed, stop the reaction.

[0065] The reaction solution was washed with saturated sodium bicarbonate, 1N dilute hydrochloric acid and water respectively, and the organic phase was collected, dried with anhydrous sodium sulfate, filtered and concentrated to obtain 280 g of crude product.

[0066] Thereafter, vacuum distillation was carried out to obtain 260 g of O, O-diethyl-p-nitrophenyl phosphate, with a yield of 94.4%.

[0067] This intermediate is an inhibitor of cholinesterase, and appropriate protection measures should be tak...

Embodiment 2

[0085] (1) Synthesis of O, O-diethyl-p-nitrophenyl phosphate

[0086] It was prepared in the same manner as in Example 1 above, and its detailed description is omitted here.

[0087] (2) Synthesis of O, O-bis(trimethylsilyl)-p-nitrophenyl phosphate

[0088] O,O-diethyl-p-nitrophenyl phosphate (260 g, 0.95 mol) and acetonitrile were added to the reaction flask. After cooling down to 0° C. in an ice bath, TMSCl (1032.1 g, 9.5 mol) was added dropwise thereto, and after the drop was completed, it was naturally raised to room temperature, and the reaction was continued for 24 h, and the reaction was completed by monitoring by phosphospectrum. The reaction solution was concentrated to obtain oily O, O-bis(trimethylsilyl)-p-nitrophenyl phosphate.

[0089] (3) Synthesis of p-nitrophenylphosphoric acid

[0090] After cooling the O,O-bis(trimethylsilyl)-p-nitrophenyl phosphate obtained in the above (2) to 0°C, drop the mixture of methanol and water into the reaction flask while stirr...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides p-nitrophenyl phosphate disodium and a preparation method thereof. The preparation method comprises the following steps: 1, enabling p-nitrophenol to react with dialkyl chloridephosphate in the presence of an alkali so as to obtain O,O-dialkyl p-nitrophenyl phosphate; 2, performing an alkyl ester desorption reaction on the O,O-dialkyl p-nitrophenyl phosphate and a compoundwith trimethylsilyl groups so as to obtain O,O-di(trimethylsilyl) p-nitrophenyl phosphate; 3, performing a hydrolysis reaction on the O,O-di(trimethylsilyl) p-nitrophenyl phosphate so as to obtain p-nitrophenyl phosphate; and 4, enabling the p-nitrophenyl phosphate to react with sodium hydroxide, so as to obtain the p-nitrophenyl phosphate disodium. According to the preparation method provided bythe invention, the intermediate product obtained in the step 1 can be purified through vacuum distillation, and byproducts which are hard to remove are not generated in later operation of ether hydrolysis or pH value adjustment, so that the purification difficulty of the product is greatly reduced; and due to selection of the compound with the trimethylsilyl groups, hydrolysis can be implemented thoroughly, and in addition, the system can be clean.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to disodium p-nitrophenylphosphate (pNPP) and a preparation method thereof. Background technique [0002] Disodium p-nitrophenylphosphate is also known as 4-nitrophenylphosphate disodium salt hexahydrate. It is mainly used as a non-protein chromogenic substrate for enzyme-linked immunosorbent assay (ELISA) and conventional spectrophotometric determination of alkaline and acid phosphatases. It is a phosphatase activity detection agent and an important chemical in the field of pharmaceutical and pesticide synthesis. intermediate. [0003] In the prior art, the synthesis technology of disodium p-nitrophenylphosphate provided by using p-nitrophenol as a raw material mainly includes the following three methods. [0004] Method 1: Utilize p-nitrophenol as a raw material, react with anhydrous phosphoric acid to obtain the substrate bis (p-nitrophenyl) phosphate for measuring ph...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/12
CPCC07F9/12
Inventor 蒋兆芹李宏林杨晨
Owner 安徽昊帆生物有限公司
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com