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

Uses

Different sources of media describe the Uses of 10123-62-3 differently. You can refer to the following data:
1. Diethyl (2-cyanoethyl)phosphonate, is a useful reactant used in various chemical synthesis such as in synthesis of lipophilic oxoamides with activity against phospholipase A2, Triose phosphate isomerase of muscle inhibitors, and also in base-catalyzed stereospecific anti-Markovnikov addition.
2. Reactant for:Heteroatom-directed alkyl cyanation of alkynesUse as a fluorescent substrate for carbon-phosphorous lyaseMicrowave-assisted cleavage of phosphate, phosphonate, and phorphoramide estersAmination and stereoselective olefination for synthesis of HIV-1 antiviralsReactant for synthesis of: Base-catalyzed stereospecific anti-Markovnikov addition reactantsLipophilic oxoamides with activity against phospholipase A2Triose phosphate isomerase of muscle inhibitors

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

Upstream product

• 542-76-7 3-Chloropropionitrile 
• 2303-76-6 sodium diethyl phosphite 
• 93115-66-3 diethyl-(2-cyano-ethyl)-methyl-ammonium; iodide 
• 122-52-1 triethyl phosphite 
• 94627-35-7 1-(2-cyano-ethyl)-1-methyl-piperidinium; iodide 
• 36240-50-3 diethyl 2-cyano-2-trimethylsilylethanephosphonate 
• 762-04-9 Diethyl phosphonate 
• 107-13-1 acrylonitrile 
• 79-06-1 2-propenamide 
• 762-04-9 phosphonic acid diethyl ester 
• 1738-25-6 3-dimethylaminopropiononitrile 
• 934538-82-6 thiophosphoric acid S-[2-(2-bromo-phenyl)-ethyl] ester O,O'-diethyl ester 
• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 4554-16-9 2,3-dibromopropionitrile 

Downstream Products

• 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 
• 69549-53-7 α-Amino-γ-diaethylphosphonopropyliden>-α,α-diphosphonsaeure 
• 4402-24-8 diethyl 3-aminopropan-1-ylphosphonate 
• 5962-42-5 3-phosphonopropionic acid 

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.