Methyl cyanoformate
Names | |
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Preferred IUPAC name
Methyl carbonocyanidate | |
Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.037.826 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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
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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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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
lachrymatory effects.[3]
References
- ISSN 0936-5214.
- ^ Sartori, Mario (1939). The War Gases (PDF).