Methyl cyanoformate

Methyl cyanoformate
Names
	IUPAC name Methyl cyanoformate
Identifiers
CAS Number	17640-15-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	26657 ;
ECHA InfoCard	100.037.826
PubChem CID	28660;
CompTox Dashboard (EPA)	DTXSID1066235 ;
	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/cm3
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. When a lithium enolate is generated in diethyl ether or methyl t-butyl ether (but not THF), 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.

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

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
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.

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[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.