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Methyl cyanoformate

Names
Preferred IUPAC name Methyl carbonocyanidate
Identifiers
CAS Number	17640-15-2
3D model (JSmol)	Interactive image
ChemSpider	26657
ECHA InfoCard	100.037.826
PubChem CID	28660
UNII	7S9M7F9JLT
CompTox Dashboard (EPA)	DTXSID1066235
InChI InChI=1S/C3H3NO2/c1-6-3(5)2-4/h1H3Key: OBWFJXLKRAFEDI-UHFFFAOYSA-N InChI=1/C3H3NO2/c1-6-3(5)2-4/h1H3Key: OBWFJXLKRAFEDI-UHFFFAOYAH
SMILES N#CC(=O)OC
Properties
Chemical formula	C3H3NO2
Molar mass	85.06
Appearance	colorless liquid
Density	1.072 g/cm
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 , 100 kPa). Y verify (what is  ?) 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, 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. 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.

References

1. ^ 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.
2. Sartori, Mario (1939). The War Gases. New York: D. Von Nostrand. p. 100.

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