Methyl isothiocyanate
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| Names | |||
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| Preferred IUPAC name
Isothiocyanatomethane | |||
| Other names
MITC, Trapex, Trapex, Vorlex, MITC-Fume, MIT, Morton EP-161E, WN 12
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| Identifiers | |||
3D model (JSmol)
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| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.008.303 | ||
| EC Number |
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| KEGG | |||
PubChem CID
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| UNII | |||
| UN number | 2477 | ||
CompTox Dashboard (EPA)
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| 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 | |||
| GHS labelling: | |||
   
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| Danger | |||
| H301, H314, H317, H331, H410 | |||
| P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P321, P330, P333+P313, P363, P391, P403+P233, P405, P501 | |||
| NFPA 704 (fire diamond) | |||
| Safety data sheet (SDS) | ACC# 07204 | ||
| Structure | |||
| 3.528 D | |||
| Related compounds | |||
Related compounds
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Methyl isocyanate Methyl thiocyanate | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
Synthesis
[edit]It is prepared industrially by two routes. Annual production in 1993 was estimated to be 4,000 tonnes.[citation needed] The main method involves the thermal rearrangement of methyl thiocyanate:[1]
- 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.[2]
MITC forms naturally upon the enzymatic degradation of glucocapparin, a glucoside found in capers.
Reactions
[edit]A characteristic reaction is with amines to give methyl thioureas:
- CH3NCS + R2NH → R2NC(S)NHCH3
Other nucleophiles add similarly.
Applications
[edit]Solutions of MITC are used in agriculture as soil fumigants, mainly for protection against fungi and nematodes.[3]
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[4]), although the compound is question (Ex6) is with EITC.
Safety
[edit]MITC is a dangerous lachrymator as well as being poisonous.
See also
[edit]References
[edit]- ^ a b Romanowski, F.; Klenk, H. "Thiocyanates and Isothiocyanates, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_749. ISBN 978-3527306732.
- ^ Moore, M. L.; Crossley, F. S. (1941). "Methyl Isothiocyanate". Organic Syntheses. 21: 81; Collected Volumes, vol. 3, p. 599.
- ^ Hartwig, Jürgen; Sommer, Herbert; Müller, Franz (2008). "Nematicides". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_125.pub2. ISBN 978-3527306732.
- ^ U.S. patent 3,417,085