Diethyl cyanomethylphosphonate, 96%, Thermo Scientific Chemicals

Product Code	Brand	Quantity
11449552	Thermo Scientific Alfa Aesar A10218.14	25 g
11459552	Thermo Scientific Alfa Aesar A10218.22	100 g
11469552	Thermo Scientific Alfa Aesar A10218.36	500 g

Description

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
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.

Solubility
Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride.

Notes
Incompatible with acids, bases, oxidizing agents and reducing agents.

Chemical Identifiers

• CAS: 2537-48-6
• Molecular Weight (g/mol): 177.14
• InChI Key: KWMBADTWRIGGGG-UHFFFAOYSA-N
• PubChem CID: 75676
• SMILES: CCOP(=O)(CC#N)OCC

• Molecular Formula: C6H12NO3P
• MDL Number: MFCD00001893
• Synonym: diethyl cyanomethylphosphonate, diethyl cyanomethyl phosphonate, diethylphosphono acetonitrile, cyanomethylphosphonic acid diethyl ester, diethylphosphonoacetonitrile, diethylcyanomethylphosphonate, diethyl cyanomethanephosphonate, phosphonic acid, cyanomethyl-, diethyl ester, cyanomethyl phosphonic acid diethyl ester
• IUPAC Name: 2-diethoxyphosphorylacetonitrile

Specifications

• CAS: 2537-48-6
• Boiling Point: 132°C to 135°C (1.2 mmHg)
• Molecular Formula: C6H12NO3P
• MDL Number: MFCD00001893
• Beilstein: 1772981
• Solubility Information: Miscible with water,chloroform,terahydrofuran,ethyl acetate and methylene chloride.
• SMILES: CCOP(=O)(CC#N)OCC
• Molecular Weight (g/mol): 177.14
• Formula Weight: 177.14
• Chemical Name or Material: Diethyl cyanomethylphosphonate

• Density: 1.094
• Flash Point: >110°C (230°F)
• Refractive Index: 1.433
• UN Number: UN3278
• Synonym: diethyl cyanomethylphosphonate, diethyl cyanomethyl phosphonate, diethylphosphono acetonitrile, cyanomethylphosphonic acid diethyl ester, diethylphosphonoacetonitrile, diethylcyanomethylphosphonate, diethyl cyanomethanephosphonate, phosphonic acid, cyanomethyl-, diethyl ester, cyanomethyl phosphonic acid diethyl ester
• InChI Key: KWMBADTWRIGGGG-UHFFFAOYSA-N
• IUPAC Name: 2-diethoxyphosphorylacetonitrile
• PubChem CID: 75676
• Percent Purity: ≥98%

Safety and Handling

GHS H Statement
H331-H302-H312-H315-H319
Toxic if inhaled.
Harmful if swallowed.
Harmful in contact with skin.
Causes skin irritation.
Causes serious eye irritation.

P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P362-P501c

H302+H312+H332-H315-H319-H335

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missing translation for 'tsca' : No

Recommended Storage : Ambient temperatures

RUO – Research Use Only