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 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 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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