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Methyl isothiocyanate

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Methyl isothiocyanate
Names
IUPAC name Methylisothiocyanate
Other names MITC
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.008.303 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H3NS/c1-3-2-4/h1H3Key: LGDSHSYDSCRFAB-UHFFFAOYSA-N
  • InChI=1/C2H3NS/c1-3-2-4/h1H3Key: LGDSHSYDSCRFAB-UHFFFAOYAS
SMILES
  • S=C=NC
Properties
Chemical formula C2H3NS
Molar mass 73.12
Appearance colourless solid
Density 1.07 g cm
Melting point 31 °C (88 °F; 304 K)
Boiling point 117 °C (243 °F; 390 K)
Solubility in water low
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3 1 1W
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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
Reaction scheme: MITC and secondary amine react to form a thiourea

Other nucleophiles add similarly.

Applications

Solutions of MITC is used in agriculture as a soil fumigant, 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.

Safety

MITC is a dangerous lachrymator as well as being poisonous.

References

  1. ^ F. Romanowski, H. Klenk "Thiocyanates and Isothiocyanates, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim.
  2. Moore, M. L.; Crossley, F. S. (1955). "Methyl Isothiocyanate". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 3, p. 599.
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