29668-61-9

Basic information

• Product Name: DIETHYL (1-CYANOETHYL)PHOSPHONATE
• Synonyms: 1-Cyanoethylphosphonic acid diethyl ester;2-(Diethoxyphosphinyl)propanenitrile;NSC 135193;Diethyl (1-cyanoethyl)phosphonate 97%;DIETHYL (1-CYANOETHYL)PHOSPHONATE
• CAS NO: 29668-61-9
• Molecular Formula: C₇H₁₄NO₃P
• Molecular Weight: 191.16
• Product Categories: Horner-Wadsworth-Emmons Reagents;Olefination;C-C Bond Formation
• Mol File: 29668-61-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 140-141 °C11 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.085 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• CAS DataBase Reference: DIETHYL (1-CYANOETHYL)PHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL (1-CYANOETHYL)PHOSPHONATE(29668-61-9)
• EPA Substance Registry System: DIETHYL (1-CYANOETHYL)PHOSPHONATE(29668-61-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 2927
• WGK Germany: 3
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 29668-61-9(Hazardous Substances Data)

Usage

Description

DIETHYL (1-CYANOETHYL)PHOSPHONATE, also known as NSC 135193, is an organic compound that serves as an intermediate in the synthesis of various chemical compounds. It is characterized by its phosphonate group and a cyanoethyl group, which contribute to its unique chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
DIETHYL (1-CYANOETHYL)PHOSPHONATE is used as an intermediate in the synthesis of 4-(1-Cyanoethyl)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile (C979545), a compound derived from the crude extract of Citrullus colocynthis. This extract has been studied for its antifungal activity against various plant pathogenic fungi, indicating potential applications in the development of antifungal agents.
Used in Polymer Industry:
DIETHYL (1-CYANOETHYL)PHOSPHONATE is used as an oligomeric product in the thermal polymerization of the acrylonitrile/styrene system. Its presence in this system contributes to the formation of polymers with specific properties, making it a valuable component in the synthesis of various polymer materials.

InChI:InChI=1/C7H14NO3P/c1-4-10-12(9,11-5-2)7(3)6-8/h7H,4-5H2,1-3H3

Upstream product

• 122-52-1 triethyl phosphite 
• 19481-82-4 2-bromopropionitrile 
• 814-49-3 diethyl chlorophosphate 
• 107-12-0 propiononitrile 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 74-88-4 methyl iodide 

Downstream Products

• 60727-74-4 2-[3-Methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-propionitrile 
• 60727-74-4 2-[(8R,9S,13S,14S)-3-Methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-propionitrile 
• 60727-73-3 3β-t-Butoxy-20-carbonitrilpregna-5,17(20)-dien 
• 5456-44-0 3β-acetoxy-17-hydroxy-5α-pregnan-20-one 
• 63089-63-4 1-(α-Cyanoaethyliden)-4-t-butylcyclohexan 
• 87184-46-1 2-[2-Isopropyl-cyclopent-(E)-ylidene]-propionitrile 
• 87184-44-9 (Z)-2,3-Dimethyl-5-phenyl-pent-2-enenitrile 
• 1068-21-9 Diethyl phosphoramidate 
• 87184-56-3 (Z)-2,4-Dimethyl-3-phenyl-pent-2-enenitrile 
• 87184-45-0 (E)-2,4-Dimethyl-3-phenyl-pent-2-enenitrile 
• 87184-46-1 2-[2-Isopropyl-cyclopent-(Z)-ylidene]-propionitrile 
• 74845-05-9 (R,S)-2-cyano-3-(2'-nitrophenyl)propene 
• 219692-69-0 2-diethylphosphono-2-phenylsulfinylpropionitrile 
• 454442-08-1 3-[3-(1-cyano-ethylidene)-cyclohex-1-enyl]-2-methyl-acrylonitrile 

Relevant articles and documents

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Application of Dually Activated Michael Acceptor to the Rational Design of Reversible Covalent Inhibitor for Enterovirus 71 3C Protease

Targeted covalent inhibitors (TCIs) have attracted growing attention from the pharmaceutical industry in recent decades because they have potential advantages in terms of efficacy, selectivity, and safety. TCIs have recently evolved into a new version with reversibility that can be systematically modulated. This feature may diminish the risk of haptenization and help optimize the drug-target residence time as needed. The enteroviral 3C protease (3Cpro) is a valuable therapeutic target, but the development of 3Cpro inhibitors is far from satisfactory. Therefore, we aimed to apply a reversible TCI approach to the design of novel 3Cpro inhibitors. The introduction of various substituents onto the α-carbon of classical Michael acceptors yielded inhibitors bearing several classes of warheads. Using steady-state kinetics and biomolecular mass spectrometry, we confirmed the mode of reversible covalent inhibition and elucidated the mechanism by which the potency and reversibility were affected by electronic and steric factors. This research produced several potent inhibitors with good selectivity and suitable reversibility; moreover, it validated the reversible TCI approach in the field of viral infection, suggesting broader applications in the design of reversible covalent inhibitors for other proteases.

Synthesis and chemical reactions of 1-cyano-1- isocyanoalkylphosphonic acid esters

1-Cyano-1-isocyanoalkylphosphonic acid esters 4 were synthesized starting from cyanoalkyl-phosphonic acid esters 1 by amination and formylation followed by dehydration with trichloromethylchloroformate (diphosgene) and triethylamine at low temperatures. B