67629-62-3

Basic information

• Product Name: (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate
• Synonyms: (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate
• CAS NO: 67629-62-3
• Molecular Formula: C₉H₁₇O₅P
• Molecular Weight: 268.200841
• Mol File: 67629-62-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 315.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.119±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate(67629-62-3)
• EPA Substance Registry System: (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate(67629-62-3)

Safety Data

• Hazardous Substances Data: 67629-62-3(Hazardous Substances Data)

Usage

Description

(E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate, with the molecular formula C9H17O5P, is a chemical compound that serves as a versatile synthetic intermediate. It is a clear, colorless liquid with a slightly fruity odor and is stable under normal conditions. (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate is also known for its pesticidal properties and is commonly used as a pesticide intermediate. Due to its moderate toxicity and potential for skin and eye irritation, caution is advised during handling. However, it is not expected to bioaccumulate in the environment, which makes it suitable for specific agricultural and industrial applications.

Uses

Used in Pesticide Industry:
(E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate is used as a pesticide intermediate for its pesticidal properties, helping to control and manage various pests that can damage crops and affect agricultural productivity.
Used in Organic Synthesis:
As a versatile synthetic intermediate, (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate is used in the production of various organic compounds. Its unique chemical structure allows for its incorporation into a wide range of molecules, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Agricultural Applications:
Given its pesticidal properties and moderate toxicity, (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate is used in agricultural applications to protect crops from pests and enhance overall crop yield. Its non-bioaccumulative nature in the environment makes it a preferred choice for certain agricultural practices.
Used in Industrial Applications:
(E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate's stability and versatility in organic synthesis make it suitable for various industrial applications, where it can be used to produce a range of products, from pharmaceuticals to specialty chemicals that serve different purposes in the industry.

Upstream product

• 1117-71-1 methyl-4-bromo-2-butenoate 
• 122-52-1 triethyl phosphite 
• 623-43-8 crotonic acid methyl ester 
• 121-45-9 phosphorous acid trimethyl ester 
• 1117-71-1 methyl 4-bromocrotonate 
• 78-40-0 triethyl phosphate 

Downstream Products

• 4807-58-3 methyl 13-desmethyl-retinoate 
• 5507-79-9 methyl 9,13-bisdesmethylretinoate 
• 7328-33-8 methyl (2E,4E)-decadienoate 
• 6190-46-1 methyl (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoate 
• 101492-92-6 methyl 10-benzyloxy-(2E,4E)-decadienoate 
• 92356-72-4 methyl (2E,4E)-5-((p-methyl)phenyl)penta-2,4-dienoate 
• 92356-70-2 methyl (2E,4E)-5-((p-chloro)phenyl)penta-2,4-dienoate 
• 92356-69-9 methyl (2E,4E)-5-(3-nitrophenyl)-2,4-pentadienoate 
• 92356-68-8 (2E,4E)-5-(4-Nitro-phenyl)-penta-2,4-dienoic acid methyl ester 
• 17171-08-3 methyl (2E,4E)-5-((p-methoxy)phenyl)penta-2,4-dienoate 
• 92356-67-7 (2E,4E)-5-(3,4-Dimethoxy-phenyl)-penta-2,4-dienoic acid methyl ester 
• 4493-42-9 methyl (2E,4Z)-deca-2,4-dienoate 
• 92356-71-3 (2E,4E)-5-(4-Bromo-phenyl)-penta-2,4-dienoic acid methyl ester 
• 92356-73-5 5t-(4-dimethylamino-phenyl)-penta-2t,4-dienoic acid methyl ester 

Relevant articles and documents

Stereoselective ozonolysis of TMS-substituted allylic alcohol derivatives and synthesis of 14R,15 S - And 14 S,15 S-diHETE

Ozonolysis of TMS-substituted olefins produces α-carbonyl TMS peroxides without cleavage of the CC bond. Herein, stereochemistry in the ozonolysis was studied using silyl derivatives of (E)- and (Z)-(1-TMS)alk-1-en-3-ols. The (E)-isomers afforded the anti-3-siloxy-2-(TMS-oxy)aldehydes as the major stereoisomer (anti/syn = 3-9:1) after reductive work-up with Ph3P. In contrast, Z-olefins selectively gave the syn isomers with syn/anti ratios of 4-19:1. Facial selection was speculated based on the Cieplak effect. This ozonolysis was successfully applied for the synthesis of 14R,15S- and 14S,15S-diHETEs (anti and syn isomers, respectively) in enantioenriched forms.

A NIR fluorescent probe for fatty acid amide hydrolase bioimaging and its application in development of inhibitors

Fatty acid amide hydrolase (FAAH) is primarily responsible for the inactivation of fatty acid ethanolamide (FAE) and is involved in a variety of biological functions related to diseases of the nervous system. Herein, we developed a highly selective and sensitive FAAH-activated near-infrared fluorescent probe named DAND and achieved the real-time detection and imaging of FAAH activity in complex biosystems. Moreover, a visual high-throughput screening method was established using DAND, piperine was identified as a novel inhibitor of FAAH. Based on the interaction of piperine with FAAH, a more potent FAAH inhibitor (11f) was designed and synthesized which possessed an IC50 value of 0.65 μM. Furthermore, 11f could attenuate the liposaccharide (LPS)-induced activation of BV2 cells, exhibiting an excellent anti-inflammatory activity. These results indicated that DAND could be used as a promising molecular tool for exploring FAAH activity and for rapidly screening potential FAAH inhibitors. In addition, piperine and its derivatives could serve as potential candidate drugs for the treatment of neurodegenerative diseases in the future.

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