Diethyl cyanomethylphosphonate - ≥98%(GC) , CAS No.2537-48-6

CAS: 2537-48-6 Cat. No.: D138560 Molecular Weight: 177.14 Beilstein Registry Number: 1772981 EC Number: 219-806-0

GRADE & PURITY ≥98%(GC)

Synonyms

Cyanomethylphosphonic acid diethyl ester | cyanomethyl-phosphonic acid diethyl ester | FT-0624834 | AB00168 | J-802187 | (Cyanomethyl)diethoxyphosphine oxide | Diethyl cyanomethanephosphonate | (EtO)2POCH2CN | cyanomethyl phosphonic acid diethylester | (D

Storage

Room temperature,Argon charged,Cool

Shipped In

Normal

Overview

Application

Diethyl cyanomethyl phosphonate is used as an intermediate in Horner-Emmons reaction for the synthesis of substituted nitriles and their amide and heterocyclic derivatives. It is known as a modified Wittig reagent used in the preparation of alpha, beta-unsaturated nitriles from ketones or aldehydes like 3-hydroxy-3-methylbutanal. It reacts with epoxides and nitrones to prepare cyano-substituted cyclopropanes and aziridines respectively. It is actively involved in the synthesis of alpha-arylated alkanenitriles via reaction with aryl iodides in presence of CuI.

Specifications

Synonyms

Cyanomethylphosphonic acid diethyl ester | cyanomethyl-phosphonic acid diethyl ester | FT-0624834 | AB00168 | J-802187 | (Cyanomethyl)diethoxyphosphine oxide | Diethyl cyanomethanephosphonate | (EtO)2POCH2CN | cyanomethyl phosphonic acid diethylester | (D

Specifications & Purity

≥98%(GC)

Storage

Room temperature, Argon charged, Cool

Shipped In

Normal

Purity

≥98%(GC)

Names and Identifiers

• Pubchem Sid: 488185151
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488185151
• Canonical Smiles: CCOP(=O)(CC#N)OCC
• IUPAC Name: 2-diethoxyphosphorylacetonitrile
• InChIKey: KWMBADTWRIGGGG-UHFFFAOYSA-N
• INCHI: 1S/C6H12NO3P/c1-3-9-11(8,6-5-7)10-4-2/h3-4,6H2,1-2H3
• Isomeric SMILES: CCOP(=O)(CC#N)OCC
• WGK Germany: 3
• Molecular Weight: 177.14
• Beilstein: 1772981
• Reaxy-Rn: 1772981
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1772981&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Organic phosphonic acids and derivatives
      • Subclass Phosphonic acid diesters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Organic phosphonic acids and derivatives
• Subclass: Phosphonic acid diesters
• Intermediate Tree Nodes: Not available
• Direct Parent: Dialkyl alkylphosphonates
• Alternative Parents: Phosphonic acid esters Nitriles Organopnictogen compounds Organophosphorus compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Dialkyl alkylphosphonate - Phosphonic acid ester - Nitrile - Carbonitrile - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organophosphorus compound - Organooxygen compound - Organonitrogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as dialkyl alkylphosphonates. These are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride.
• Refractive Index: 1.434
• Flash Point(°F): 235.4 °F
• Flash Point(°C): 113 °C
• Boil Point(°C): 168 °C/22 mmHg
• Molecular Weight: 177.140 g/mol
• XLogP3: 0.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 177.055 Da
• Monoisotopic Mass: 177.055 Da
• Topological Polar Surface Area: 59.300 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 185.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1