CAS 2537-48-6 Diethyl (cyanomethyl)phosphonate (HCID 75676)

Names & identifiers

Preferred name: Diethyl (cyanomethyl)phosphonate
IUPAC: 2-diethoxyphosphorylacetonitrile
English name: Diethyl cyanomethylphosphonate
Molecular formula: C6H12NO3P
Molecular weight: 177.14

Names & synonyms

Diethyl cyanomethylphosphonate2537-48-6Diethyl (cyanomethyl)phosphonatePhosphonic acid, (cyanomethyl)-, diethyl esterEINECS 219-806-0DTXSID20180015NSC 407826RefChem:587029DTXCID30102506219-806-0InChI=1/C6H12NO3P/c1-3-9-11(8,6-5-7)10-4-2/h3-4,6H2,1-2H2-diethoxyphosphorylacetonitrile

Show more names

cyanomethyLDEPANDiethyl cyanomethylpLABOTEST-BB LT00233137Diethyl cyanomethylphosphote

(Diethylphosphono)acetonitrileDiethyl cyanomethanephosphonateCyanomethylphosphonic acid diethyl esterdiethylcyanomethylphosphonateC6H12NO3PDiethyl cyanomethyl phosphonateDiethylphosphonoacetonitrileMFCD00001893

Database identifiers

CAS: 2537-48-6
PubChem CID: 75676
DTXSID: DTXSID20180015
UNII: 5S99GCU3PT
EC Number: 219-806-0
Nikkaji: J149.878I

Properties

Computed structural properties

XLogP: 0
Topological polar surface area: 59.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 5
Heavy atoms: 11
Formal charge: 0
Complexity: 185

Physicochemical properties

Boiling point: 101 · 101-102 °C0.4 mm Hg(lit.)
Density: 1.095 g/mL · 1.095 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.434(lit.)
Flash point: 230 °F · >230 °F
storage temp.: 2 · Inert atmosphere,2-8°C
solubility: Chloroform (Soluble), Methanol (Slightly)
form: Liquid
color: Clear colorless to light yellow
Specific Gravity: 1.1261 · 1.1261.095
Water Solubility: Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride.
BRN: 1772981 · 1772981
InChI: InChI=1S/C6H12NO3P/c1-3-9-11(8,6-5-7)10-4-2/h3-4,6H2,1-2H3
InChIKey: KWMBADTWRIGGGG-UHFFFAOYSA-N
SMILES: P(CC#N)(=O)(OCC)OCC
CAS DataBase Reference: 2537 · 2537-48-6(CAS DataBase Reference)
NIST Chemistry Reference: Diethyl cyanomethylphosphonate(2537-48-6)
UNSPSC Code: 12352108 · 12352108
NACRES: 22 · NA.22
Symbol(GHS): 6 · GHS06,GHS07
Signal word: Danger
Hazard statements: 301 · H301+H311+H331-H315-H319-H302-H312-H331
Precautionary statements: 304 · P304+P340-P305+P351+P338-P501a-P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi,Xn,C
Risk Statements: 38 · 38-36/37/38-20/21/22-34-36/38
Safety Statements: 26 · 26-28-36/37/39-23-45-27-36/37-9
RIDADR: 1760 · UN 1760 8/PG 2
WGK Germany: 3 · 3
Hazard Note: Irritant
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29310095 · 29310095
Storage Class: 10 · 10 - Combustible liquids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (32.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 67 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationDiethyl cyanomethylphosphonate: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (32.8%)

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
ridadr: UN 1760 8/PG 2
hs_code: 29310095
risk_code: 38-36/37/38-20/21/22-34-36/38
Signal word: Danger
Symbol(GHS): GHS06,GHS07
hazard_code: Xi,Xn,C
hazard_note: Irritant
safety_code: 26-28-36/37/39-23-45-27-36/37-9
hazard_class: 6.1
Storage Class: 10 - Combustible liquids
packing_group: III
Hazard statements: H301+H311+H331-H315-H319-H302-H312-H331
REACH Registrations: Active
Precautionary statements: P304+P340-P305+P351+P338-P501a-P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501

Chemistry & industry

Applications · 3 items

UsesDiethyl 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.

UsesWittig reagent.

General DescriptionDiethyl 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