Methyl cyanoformate

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.[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
Names
Preferred IUPAC name
Methyl carbonocyanidate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.037.826
UNII
  • InChI=1S/C3H3NO2/c1-6-3(5)2-4/h1H3 checkY
    Key: OBWFJXLKRAFEDI-UHFFFAOYSA-N checkY
  • InChI=1/C3H3NO2/c1-6-3(5)2-4/h1H3
    Key: OBWFJXLKRAFEDI-UHFFFAOYAH
  • N#CC(=O)OC
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).
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Infobox references

Methyl cyanoformate is also an ingredient in Zyklon A. It has lachrymatory effects.[3]

References
  1. 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
  2. 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.
  3. Sartori, Mario (1939). The War Gases (PDF).
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