Methyl cyanoformate

Methyl cyanoformate

Names
IUPAC name Methyl cyanoformate
Identifiers
CAS Number	17640-15-2
ChemSpider	26657
Jmol interactive 3D	Image
PubChem	28660
InChI InChI=1S/C3H3NO2/c1-6-3(5)2-4/h1H3 Key: OBWFJXLKRAFEDI-UHFFFAOYSA-N InChI=1/C3H3NO2/c1-6-3(5)2-4/h1H3 Key: OBWFJXLKRAFEDI-UHFFFAOYAH
SMILES N#CC(=O)OC
Properties
Chemical formula	C3H3NO2
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
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.

It is notoriously known for being an ingredient in Zyklon A, a predecessor to Zyklon B, the brand name of a German gas pesticide that was used during the Holocaust.

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