Methyl cyanoformate is the organic compound with the formula CH3OC(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.[1] 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.
| |
| Names | |
|---|---|
| Preferred IUPAC name
Methyl carbonocyanidate | |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.037.826 |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C3H3NO2 | |
| Molar mass | 85.06 |
| Appearance | colorless liquid |
| Density | 1.072 g/cm3 |
| 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 also an ingredient in Zyklon A. It has lachrymatory effects.[2]
References
edit- ^ a b 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 (3): 169–170. doi:10.1055/s-1990-21025.
- ^ Sartori, Mario (1939). The War Gases. New York: D. Von Nostrand. p. 100.
 | This article about an ester is a stub. You can help Wikipedia by expanding it. |