28325
Methyl cyanoformate
purum, ≥98.5% (GC)
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About This Item
Linear Formula:
NCCO2CH3
CAS Number:
Molecular Weight:
85.06
EC Number:
241-626-6
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
1742994
MDL number:
grade
purum
assay
≥98.5% (GC)
refractive index
n20/D 1.374
bp
100-101 °C (lit.)
density
1.072 g/mL at 25 °C (lit.)
SMILES string
COC(=O)C#N
InChI
1S/C3H3NO2/c1-6-3(5)2-4/h1H3
InChI key
OBWFJXLKRAFEDI-UHFFFAOYSA-N
Application
Methyl cyanoformate has been used in:
- enantioselective synthesis of series of pure S-(+)-2β-carboalkoxy-3α-[bis(4-fluorophenyl)methoxy]tropanes
- regioselective synthesis of β-keto esters via C-acylation of lithium enolates
- peroxide-initiated free-radical chain cyanation of several hydrocarbons
- the C-acylation of enolates
Other Notes
Reagent used for the C-acylation of enolates
signalword
Danger
Hazard Classifications
Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
78.8 °F - closed cup
flash_point_c
26 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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Mu-Fa Zou et al.
Bioorganic & medicinal chemistry letters, 12(9), 1249-1252 (2002-04-20)
Synthesis of a series of pure S-(+)-2beta-carboalkoxy-3alpha-[bis(4-fluorophenyl)methoxy]tropanes (>99% ee) was achieved by employing a chiral amine-induced asymmetric reaction of tropinone with methyl cyanoformate as the key step. In this series, all of the S-(+)-enantiomers were 2-fold more potent than their
Free-radical cyanation. Novel free-radical reaction of methyl cyanoformate or cyanogen with 2, 4-dimethylpentane.
Tanner DD and Rahimi PM.
The Journal of Organic Chemistry, 44(10), 1674-1677 (1979)
S.R. Crabtree et al.
Synlett, 169-169 (1990)
Regioselective synthesis of ?-ketoesters from lithium enolates and methyl cyanoformate.
Mander LN and Sethi SP.
Tetrahedron Letters, 24(48), 5425-5428 (1983)
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