Methyl isothiocyanate | |
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Methylisothiocyanate |
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Other names
MITC |
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Identifiers | |
CAS number | 556-61-6 |
PubChem | 11167 |
ChemSpider | 10694 |
KEGG | C18587 |
ChEMBL | CHEMBL396000 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C2H3NS |
Molar mass | 73.12 g mol−1 |
Appearance | colourless solid |
Density | 1.07 g cm–3 |
Melting point |
31 °C, 304 K, 88 °F |
Boiling point |
117 °C, 390 K, 243 °F |
Solubility in water | 8.2g/L |
Hazards | |
MSDS | ACC# 07204 |
NFPA 704 |
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3
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Structure | |
Dipole moment | 3.528 D |
Related compounds | |
Related compounds | Methyl isocyanate Methyl thiocyanate |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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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.[1]
Contents |
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:[1]
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.[2]
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 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.
MITC is a dangerous lachrymator as well as being poisonous.