10123-62-3

Basic information

• Product Name: DIETHYL (2-CYANOETHYL)PHOSPHONATE 95
• Synonyms: 2-cyanoethanephosphonicaciddiethylester;2-cyano-ethanephosphonicacidiethylester;DIETHYL (2-CYANOETHYL)PHOSPHONATE 95;3-(Diethoxyphosphinyl)propiononitrile;Ai3-16155;beta-(Diethoxyphosphinyl)propionitrile;Brn 1775584;Diethyl 2-cyanoethanephosphonate
• CAS NO: 10123-62-3
• Molecular Formula: C₇H₁₄NO₃P
• Molecular Weight: 191.164721
• EINECS: 233-327-4
• Mol File: 10123-62-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 110 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.08 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000928mmHg at 25°C
• Refractive Index: n20/D 1.4380(lit.)
• CAS DataBase Reference: DIETHYL (2-CYANOETHYL)PHOSPHONATE 95(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL (2-CYANOETHYL)PHOSPHONATE 95(10123-62-3)
• EPA Substance Registry System: DIETHYL (2-CYANOETHYL)PHOSPHONATE 95(10123-62-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: KI6650000
• Hazardous Substances Data: 10123-62-3(Hazardous Substances Data)

Usage

Description

DIETHYL (2-CYANOETHYL)PHOSPHONATE 95, also known as DCEP, is an organic compound that serves as a versatile reactant in various chemical syntheses. It is characterized by its phosphonate group and cyanoethyl moiety, which contribute to its reactivity and utility in the production of different compounds.

Uses

Used in Pharmaceutical Industry:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for the synthesis of lipophilic oxoamides with activity against phospholipase A2. These compounds have potential applications in the development of anti-inflammatory and analgesic drugs.
Used in Enzyme Inhibition:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for the synthesis of triose phosphate isomerase of muscle inhibitors. These inhibitors can be employed in the study of enzyme function and the development of therapeutic agents for muscle-related disorders.
Used in Chemical Research:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for heteroatom-directed alkyl cyanation of alkynes, which is a significant method in organic chemistry for the formation of various complex molecules.
Used in Analytical Chemistry:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a fluorescent substrate for carbon-phosphorous lyase, an enzyme involved in the degradation of organophosphorus compounds. This application aids in the study of enzyme activity and the development of detection methods for these compounds.
Used in Microwave-Assisted Chemistry:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used in microwave-assisted cleavage of phosphate, phosphonate, and phorphoramide esters. This technique allows for faster and more efficient cleavage reactions, which can be beneficial in various chemical synthesis processes.
Used in Antiviral Drug Synthesis:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for amination and stereoselective olefination in the synthesis of HIV-1 antivirals. These compounds have the potential to be developed into effective treatments for HIV and AIDS.
Used in Organic Synthesis:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for base-catalyzed stereospecific anti-Markovnikov addition reactants. This reaction is an important method in organic chemistry for the synthesis of various organic compounds with specific stereochemistry.

InChI:InChI=1/C7H14NO3P/c1-3-10-12(9,11-4-2)7-5-6-8/h3-5,7H2,1-2H3

Upstream product

• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 107-13-1 acrylonitrile 
• 762-04-9 phosphonic acid diethyl ester 
• 934538-82-6 thiophosphoric acid S-[2-(2-bromo-phenyl)-ethyl] ester O,O'-diethyl ester 
• 542-76-7 3-Chloropropionitrile 
• 122-52-1 triethyl phosphite 
• 2417-90-5 bromopropionitrile 
• 1738-25-6 3-dimethylaminopropiononitrile 
• 762-04-9 Diethyl phosphonate 
• 36240-50-3 diethyl 2-cyano-2-trimethylsilylethanephosphonate 
• 4554-16-9 2,3-dibromopropionitrile 
• 2303-76-6 sodium diethyl phosphite 
• 94627-35-7 1-(2-cyano-ethyl)-1-methyl-piperidinium; iodide 
• 93115-66-3 diethyl-(2-cyano-ethyl)-methyl-ammonium; iodide 

Downstream Products

• 5962-42-5 3-phosphonopropionic acid 
• 4402-24-8 diethyl 3-aminopropan-1-ylphosphonate 
• 69549-53-7 α-Amino-γ-diaethylphosphonopropyliden>-α,α-diphosphonsaeure 
• 1777-22-6 1-(diethoxyphosphinyl)-3-hexanone 
• 914386-20-2 (Z)-3-(4-Fluoro-phenyl)-3-(4-methoxy-phenyl)-acrylonitrile 
• 113811-57-7 diethyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-3-aminopropanephosphonate 
• 113811-51-1 monoethyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-3-aminopropanephosphonate 

Relevant articles and documents

Radical cyanomethylation via vinyl azide cascade-fragmentation

Herein, a novel methodology for radical cyanomethylation is described. The process is initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggers a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilised 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl groups can be efficiently introduced into a range of substrates via trapping of α-carbonyl, heterobenzylic, alkyl, sulfonyl and aryl radicals, generated from a variety of functional groups under both photoredox catalysis and non-catalytic conditions. The value of this approach is exemplified by the late-stage cyanomethylation of pharmaceuticals.

Amino phosphonic acids. 3. The synthesis and properties of 2-aminoethylphosphonic and 3-aminopropylphosphonic acids.

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Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid

Using an N-oleoyl ethanolamide scaffold, a series of phosphate polar head group analogues of LPA comprised of various α-substituted phosphonates and thiophosphates was prepared. In a broken cell GTP[γ35S] binding assay, agonist activity was evaluated at the three LPA receptors of the endothelial differentiation gene (Edg) family. This study has resulted in the discovery of a nonhydrolyzable LPA1-selective agonist (11). Additionally, thiophosphate 19 bears an isosteric phosphate mimetic that confers agonism at the LPA1 receptor but not LPA2.

REACTION OF α-CYANOACRYLIC ACID AND CYANOACRYLATES WITH DIALKYL AND DIARYL PHOSPHITES

α-Cyanoacrylic acid and α-cyanoacrylates add dialkyl and diaryl phosphites and diethyl thiophosphite at the C=C double bond in the absence of catalyst.This is an anti-Markpvnikov reaction, which yields the corresponding phosphonates and thiophosphonates. Keywords: alkenes, hydrophosphorylation, addition reaction, thiophosphites, thiophosphonates, phosphites, phosphonates, cyanoacrylic acid.

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In recent years phosphonylated ketones were considered as valuable intermediates in organic synthesis. In the present work we studied the reaction of cyanoalkylphosphonates 1 with organozinc compounds which led after hydrolysis to the corresponding phosph

Organophosphorus compounds. XV. Synthesis of 2 ethoxy 1 methyl 1,2 azaphospholidine 2 oxide

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PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes

PS-BEMP was used as a heterogeneous catalyst for the phospha-Michael addition of phosphorus nucleophiles to a variety of electron-poor alkenes. The addition reactions were generally performed with equimolar amounts of reagents under solvent free conditions. The protocol proved to be very efficient for the addition to aromatic, non-aromatic and cyclic ketones, giving good yields (78-85%) in all cases. The protocol was also extended with good results to α,β-unsaturated esters and nitriles. This demonstrates that PS-BEMP is a good catalyst for the phospha-Michael addition to electron-poor alkenes.