Methyl cyanoformate
Chemical compound
Names | |
---|---|
Preferred IUPAC name
Methyl carbonocyanidate
|
|
Identifiers | |
3D model (
JSmol
)
|
|
ChemSpider |
|
ECHA InfoCard | 100.037.826 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard
(
EPA
)
|
|
|
|
|
|
Properties | |
C 3 H 3 N O 2 | |
Molar mass | 85.06 |
Appearance | colorless liquid |
Density | 1.072 g/cm 3 |
Boiling point | 100 to 101 °C (212 to 214 °F; 373 to 374 K) |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
toxic |
Except where otherwise noted, data are given for materials in their
standard state
(at 25
°C [77
°F], 100
kPa).
|
Methyl cyanoformate is the organic compound with the formula CH 3 OC(O)CN. It is used as a reagent in organic synthesis as a source of the methoxycarbonyl group, [1] in which context it is also known as Mander's reagent. When a lithium enolate is generated in diethyl ether or methyl t -butyl ether, treatment with Mander's reagent will selectively afford the C-acylation product. [2] Thus, for enolate acylation reactions in which C- vs. O-selectivity is a concern, methyl cyanoformate is often used in place of more common acylation reagent like methyl chloroformate .
Methyl cyanoformate is also an ingredient in Zyklon A . It has lachrymatory effects. [3]
References
- ↑ Simon R. Crabtree, W. L. Alex Chu, Lewis N. Mander "C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site- and Stereoselectivity"Synlett 1990; 1990: 169–170. doi : 10.1055/s-1990-21025
- ↑ Crabtree, Simon R.; Chu, W. L. Alex; Mander, Lewis N. (1990). "C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site- and Stereoselectivity". Synlett . 1990 (3): 169–170. doi : 10.1055/s-1990-21025 . ISSN 0936-5214 .
- ↑ Sartori, Mario (1939). The War Gases (PDF) .