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Methyl isothiocyanate

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Appearance  colourless solid
Methyl isothiocyanate httpsuploadwikimediaorgwikipediacommonsthu
Related compounds  Methyl isocyanate Methyl thiocyanate

Methyl isothiocyanate is the organosulfur compound with the formula CH3N=C=S. This low melting colorless solid is a powerful lachrymator. As a precursor to a variety of valuable bioactive compounds, it is the most important organic isothiocyanate in industry.

Contents

Synthesis

It is prepared industrially by two routes. Annual production in 1993 was estimated to be 4M kg. The main method involves the thermal rearrangement of methyl thiocyanate:

CH3S-C≡N → CH3N=C=S

It is also prepared via with the reaction of methylamine with carbon disulfide followed by oxidation of the resulting dithiocarbamate with hydrogen peroxide. A related method is useful to prepare this compound in the laboratory.

MITC forms naturally upon the enzymatic degradation of glucocapparin, a modified sugar found in capers.

Reactions

A characteristic reaction is with amines to give methyl thioureas:

CH3NCS + R2NH → R2NC(S)NHCH3

Other nucleophiles add similarly.

Applications

Solutions of MITC are used in agriculture as soil fumigants, mainly for protection against fungi and nematodes.

MITC is a building block for the synthesis of 1,3,4-thiadiazoles, which are heterocyclic compounds used as herbicides. Commercial products include "Spike", "Ustilan," and "Erbotan."

Well known pharmaceuticals prepared using MITC include Zantac and Tagamet. Suritozole is a third example.

MITC is used in the Etasuline patent (Ex2), although the compound is question (Ex6) is with EITC.

Safety

MITC is a dangerous lachrymator as well as being poisonous.

References

Methyl isothiocyanate Wikipedia


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