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
Methyl cyanoformate Structural Formulae V.1.svg
Preferred IUPAC name
Methyl carbonocyanidate
3D model (JSmol)
ECHA InfoCard 100.037.826 Edit this at Wikidata
  • InChI=1S/C3H3NO2/c1-6-3(5)2-4/h1H3 checkY
  • InChI=1/C3H3NO2/c1-6-3(5)2-4/h1H3
  • N#CC(=O)OC
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)
Occupational safety and health (OHS/OSH):
Main hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methyl cyanoformate is also an ingredient in Zyklon A. It has lachrymatory effects.[3]


  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).