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.^[1] 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.

Quick facts Names, Identifiers ...

Methyl cyanoformate

Names
Preferred IUPAC name Methyl carbonocyanidate
Identifiers
CAS Number	17640-15-2 Y
3D model (JSmol)	Interactive image
ChemSpider	26657 Y
ECHA InfoCard	100.037.826
PubChem CID	28660
UNII	7S9M7F9JLT Y
CompTox Dashboard (EPA)	DTXSID1066235
InChI InChI=1S/C3H3NO2/c1-6-3(5)2-4/h1H3 Y Key: OBWFJXLKRAFEDI-UHFFFAOYSA-N Y 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/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). Y verify (what is YN ?) Infobox references

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Methyl cyanoformate is also an ingredient in Zyklon B. It has lachrymatory effects.^[2]