319813
Methyl cyanoformate
99%
Synonym(s):
2-Methoxy-2-oxoacetonitrile, Cyanoformic acid methyl ester, Mander′s reagent, Methyl carbonocyanidate, [(Cyanocarbonyl)oxy]methane
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About This Item
Linear Formula:
NCCO2CH3
CAS Number:
Molecular Weight:
85.06
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
241-626-6
Beilstein/REAXYS Number:
1742994
MDL number:
Assay:
99%
Form:
liquid
Quality Level
assay
99%
form
liquid
refractive index
n20/D 1.374 (lit.)
bp
100-101 °C (lit.)
density
1.072 g/mL at 25 °C (lit.)
functional group
ester, nitrile
SMILES string
COC(=O)C#N
InChI
1S/C3H3NO2/c1-6-3(5)2-4/h1H3
InChI key
OBWFJXLKRAFEDI-UHFFFAOYSA-N
General description
Methyl cyanoformate is an organic compound that is commonly used as a source of the methoxycarbonyl group in organic synthesis. It is most frequently used as a reagent to synthesize regioselective β-keto esters via C-acylation of lithium enolates. In comparison with more traditional reagents such as acyl halides, anhydrides, and carbon dioxide, it is regarded as a superior acylating agent.
Application
Selective acylating reagent.
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
危险化学品
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Aldrichimica Acta, 20, 53-53 (1987)
Tetrahedron Letters, 34, 8553-8553 (1993)
D L Selwood et al.
Journal of medicinal chemistry, 36(23), 3503-3510 (1993-11-12)
A variety of isosteres of the DNA polymerase inhibitor aphidicolin were synthesized as potential antiherpes agents. Modeling studies indicated that the bicyclooctane C, D rings of aphidicolin could be replaced by an aromatic moiety while maintaining the spatial arrangement of
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 319813-25G | 04061837498657 |
| 319813-5G | 04061837498664 |