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HomeProduct name listDiethyl cyanomethylphosphonate

Diethyl cyanomethylphosphonate

Synonym(s):(Diethylphosphono)acetonitrile;Cyanomethylphosphonic acid diethyl ester

  • CAS NO.:2537-48-6
  • Empirical Formula: C6H12NO3P
  • Molecular Weight: 177.14
  • MDL number: MFCD00001893
  • EINECS: 219-806-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-05-31 17:33:32
Diethyl cyanomethylphosphonate Structural

What is Diethyl cyanomethylphosphonate?

Chemical properties

clear colorless to light yellow liquid

The Uses of Diethyl cyanomethylphosphonate

Wittig reagent.

The Uses of Diethyl cyanomethylphosphonate

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.

Biological Functions

Diethyl cyanomethylphosphonate can be used to inhibit and/0r prevent the growth of undesirable algae, bacteria, fungi, yeast, and other microorganisms.

General Description

Diethyl cyanomethylphosphonate is a useful chemical and medical intermediate, which can be used as raw material to synthesize nitrogen-haloamine precursor AEP-ADCT containing triazine-phosphate group

Properties of Diethyl cyanomethylphosphonate

Boiling point: 101-102 °C0.4 mm Hg(lit.)
Density  1.095 g/mL at 25 °C(lit.)
refractive index  n20/D 1.434(lit.)
Flash point: >230 °F
storage temp.  Inert atmosphere,2-8°C
solubility  Chloroform (Soluble), Methanol (Slightly)
form  Liquid
color  Clear colorless to light yellow
Specific Gravity 1.1261.095
Water Solubility  Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride.
BRN  1772981
InChI InChI=1S/C6H12NO3P/c1-3-9-11(8,6-5-7)10-4-2/h3-4,6H2,1-2H3
CAS DataBase Reference 2537-48-6(CAS DataBase Reference)
NIST Chemistry Reference Diethyl cyanomethylphosphonate(2537-48-6)

Safety information for Diethyl cyanomethylphosphonate

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H312:Acute toxicity,dermal
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H331:Acute toxicity,inhalation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.
P403+P233:Store in a well-ventilated place. Keep container tightly closed.
P501:Dispose of contents/container to..…

Computed Descriptors for Diethyl cyanomethylphosphonate

InChIKey KWMBADTWRIGGGG-UHFFFAOYSA-N
SMILES P(CC#N)(=O)(OCC)OCC

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