Methyl cyanoformate

Structural formula
General
Surname	Methyl cyanoformate
other names	Cyclone A; Methyl Cyanoformate (English); Methyl cyanoformate; Mander's reagent;
Molecular formula	C 3 H 3 NO 2
Brief description	slightly yellowish, clear liquid
External identifiers / databases
EC number	241-626-6
ECHA InfoCard	100,037,826
PubChem	28660
Wikidata	Q415666
properties
Molar mass	85.06 g mol −1
Physical state	liquid
density	1.07 g cm −3 (25 ° C)
boiling point	100-101 ° C
safety instructions
H and P phrases	H: 226-300-310-315-319-330
	P: 260-264-280-284-302 + 350-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Methyl cyanoformate (common name : Zyklon A , trade name: Zyklon ) is a pesticide from the group of carboxylic acid esters and nitriles , which was used to destroy vermin in rooms and effects . It is the nitrile to the oxalic acid monomethyl ester .

history

The German Pest Control Society (Degesch) was founded in March 1919, and Walter Heerdt was in charge of it from 1920 . Ferdinand Flury , who like Heerdt and Bruno Tesch, was a former colleague of Fritz Haber , developed Zyklon A and received the patent for it in 1920. Up to now, handling the relatively weak-smelling and rapidly evaporating hydrocyanic acid has been too dangerous. The aim were substances whose toxicity was comparable, but which could guarantee greater handling safety thanks to a pungent warning smell. Flury's first experiments with methyl cyanoformate showed that the methyl chloroformate contained in raw Zyklon A , a residue from the synthesis, could act as a warning substance.

Zyklon A is the forerunner of Zyklon B , in which hydrocyanic acid is slowly and controlled desorbed from porous carrier substances.

The manufacture was banned by the Peace Treaty of Versailles in Germany because it can be used as a chemical warfare agent. Contact with the substance, whether through inhalation, ingestion or absorption through the skin, can lead to severe symptoms such as paralysis, shortness of breath, edema , cyanosis and even death.

presentation

Methyl cyanoformate can be prepared by simply reacting methyl chloroformate and alkali metal cyanides , such as potassium cyanide or sodium cyanide .

use

Today, methyl cyanoformate is mainly used as a reagent , for example for the acylation of enolates . In this context, it is also known as Mander's reagent , named after the New Zealand chemist Lewis Norman Mander .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet Methyl cyanoformate from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).
↑ Patent DE351894 : Process for pest control using poisonous gases or fumes. Registered April 9, 1920 , published April 18, 1922 . , Applicant: Dr. Ferdinand Flury; Degesch
^ The judgments against the suppliers of the Zyklon-B ( Memento from June 16, 2012 in the Internet Archive )
↑ Simon R. Crabtree, WL Alex Chu, Lewis N. Mander: C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site and Stereoselectivity , Synlett 1990; 1990 (3): 169-170. doi: 10.1055 / s-1990-21025

[SIGMA-1] ↑ ^a ^b ^c ^d ^e ^f data sheet Methyl cyanoformate from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).

[2] Patent DE351894 : Process for pest control using poisonous gases or fumes. Registered April 9, 1920 , published April 18, 1922 . , Applicant: Dr. Ferdinand Flury; Degesch

[3] The judgments against the suppliers of the Zyklon-B ( Memento from June 16, 2012 in the Internet Archive )

[4] Simon R. Crabtree, WL Alex Chu, Lewis N. Mander: C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site and Stereoselectivity , Synlett 1990; 1990 (3): 169-170. doi: 10.1055 / s-1990-21025