Methyl cyanoformate is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

CH₃OC(O)CN. It is used as a

reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

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 In chemistry, acylation (or alkanoylation) is the chemical reaction in which an acyl group () is added to a compound. The compound providing the acyl group is called the acylating agent. Because they form a strong electrophile when treated with ...

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 chloroformate is the methyl ester of chloroformic acid. It is an oily colorless liquid, although aged samples appear yellow. It is also known for its pungent odor. Preparation Methyl chloroformate can be synthesized using methanol and p ...

. Methyl cyanoformate is also an ingredient in

Zyklon A Zyklon B (; translated Cyclone B) was the trade name of a cyanide-based pesticide invented in Germany in the early 1920s. It consisted of hydrogen cyanide (prussic acid), as well as a cautionary eye irritant and one of several adsorbents such ...

. It has

lachrymatory Lachrymatory or lacrymatory may refer to: * Something that has the effect of ''lachrymation'', causing the secretion of tears * Tear gas Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" af ...

effects.

References

Methyl esters Carboxylate esters Reagents for organic chemistry Nitriles Fumigants Blood agents Lachrymatory agents {{ester-stub