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Methyl isothiocyanate

Methyl isothiocyanate
Methyl isothiocyanate.png
Methyl isothiocyanate-3D-balls-by-AHRLS-2012.png
Methyl isothiocyanate-3D-vdW-by-AHRLS-2012.png
Names
IUPAC name
Methylisothiocyanate
Other names
MITC
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.303
KEGG
PubChem CID
Properties
C2H3NS
Molar mass 73.12
Appearance colourless solid
Density 1.07 g cm−3
Melting point 31 °C (88 °F; 304 K)
Boiling point 117 °C (243 °F; 390 K)
8.2g/L
Hazards
Safety data sheet ACC# 07204
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Structure
3.528 D
Related compounds
Related compounds
 Methyl isocyanate
Methyl thiocyanate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

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.

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:

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.

A characteristic reaction is with amines to give methyl thioureas:

Other nucleophiles add similarly.

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.

MITC is a dangerous lachrymator as well as being poisonous.


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Wikipedia

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