| Revision as of 09:29, 25 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 402391380 |
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|verifiedrevid = 415837766 |
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|ImageFileL1=Methyl isothiocyanate.png |
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|ImageFileL1= |
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|ImageFileR1=<!-- Methyl-isothiocyanate-3D-vdW.png --> |
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|ImageSizeL1=100px |
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|ImageFileR1=Methyl-isothiocyanate-3D-vdW.png |
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|ImageFile1 = Methyl isothiocyanate.png |
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|ImageSize1 = 120px |
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|ImageSizeR1=120 |
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|ImageFileL2 = Methyl isothiocyanate-3D-balls-by-AHRLS-2012.png |
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|IUPACName= Methylisothiocyanate |
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|ImageSizeL2 = 120px |
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|OtherNames= MITC |
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|ImageFileR2 = Methyl isothiocyanate-3D-vdW-by-AHRLS-2012.png |
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|ImageSizeR2 = 120px |
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|PIN= Isothiocyanatomethane |
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|OtherNames= MITC, Trapex, Trapex, Vorlex, MITC-Fume, MIT, Morton EP-161E, WN 12 |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo=556-61-6 |
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| ChemSpiderID = 10694 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = 1/C2H3NS/c1-3-2-4/h1H3 |
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|ChemSpiderID = 10694 |
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| InChIKey = LGDSHSYDSCRFAB-UHFFFAOYAS |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 396000 |
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|ChEBI = 78337 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| StdInChI = 1S/C2H3NS/c1-3-2-4/h1H3 |
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|ChEMBL = 396000 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|EINECS = 209-132-5 |
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| StdInChIKey = LGDSHSYDSCRFAB-UHFFFAOYSA-N |
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|PubChem = 11167 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| CASNo=556-61-6 |
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| PubChem = 11167 |
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|KEGG = C18587 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = S=C=NC |
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|UNII = RWE2M5YDW1 |
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|UNNumber = 2477 |
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|InChI = 1/C2H3NS/c1-3-2-4/h1H3 |
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|InChIKey = LGDSHSYDSCRFAB-UHFFFAOYAS |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C2H3NS/c1-3-2-4/h1H3 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = LGDSHSYDSCRFAB-UHFFFAOYSA-N |
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|SMILES = S=C=NC |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=2 | H = 3 | N = 1 | S = 1 |
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|C=2 | H=3 | N=1 | S=1 |
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| MolarMass= 73.12 |
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|MolarMass= 73.12 |
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| Appearance= colourless solid |
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|Appearance= colourless solid |
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| Density= 1.07 g cm<sup>–3</sup> |
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|Density= 1.07 g cm<sup>−3</sup> |
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| MeltingPtC= 31 |
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|MeltingPtC= 31 |
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| BoilingPtC= 117 |
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|BoilingPtC= 117 |
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| Solubility= low |
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|Solubility= 8.2g/l |
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}} |
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|Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| ExternalMSDS = |
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|ExternalSDS = |
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| MainHazards = |
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|NFPA-H = 3 |
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| NFPA-H = 3 |
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|NFPA-F = 1 |
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| NFPA-F = 1 |
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|NFPA-R = 1 |
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|GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}} |
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| NFPA-R = 1 |
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|GHSSignalWord = Danger |
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| NFPA-O = W |
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|HPhrases = {{H-phrases|301|314|317|331|410}} |
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}} |
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|PPhrases = {{P-phrases|260|261|264|270|271|272|273|280|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|311|321|330|333+313|363|391|403+233|405|501}} |
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|Section4 = {{Chembox Related |
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| OtherCpds = ] |
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|Section4={{Chembox Structure |
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|Dipole = 3.528 ] |
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|Section5={{Chembox Related |
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|OtherCompounds = ]<br />] |
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'''Methyl isothiocyanate''' is the ] with the ] CH<sub>3</sub>N=C=S. This low melting colorless solid is a powerful ]. As a precursor to a variety of valuable bioactive compounds, it is the most important organic ] in industry.<ref name=Ullmann>F. Romanowski, H. Klenk "Thiocyanates and Isothiocyanates, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim.</ref> |
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'''Methyl isothiocyanate''' is the ] with the ] CH<sub>3</sub>N=C=S. This low melting colorless solid is a powerful ]. As a precursor to a variety of valuable bioactive compounds, it is the most important organic ] in industry.<ref name=Ullmann>{{Ullmann | author = Romanowski, F. | author2 = Klenk, H. | title = Thiocyanates and Isothiocyanates, Organic | doi = 10.1002/14356007.a26_749}}</ref> |
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==Synthesis== |
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==Synthesis== |
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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:<ref name=Ullmann/> |
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It is prepared industrially by two routes. Annual production in 1993 was estimated to be 4,000 tonnes.{{cn|date=May 2021}} The main method involves the thermal rearrangement of methyl thiocyanate:<ref name=Ullmann/> |
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:CH<sub>3</sub>S-C≡N → CH<sub>3</sub>N=C=S |
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:CH<sub>3</sub>S−C≡N → CH<sub>3</sub>N=C=S |
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It is also prepared via with the reaction of ] with ] followed by oxidation of the resulting ] with ]. A related method is useful to prepare this compound in the laboratory.<ref>{{OrgSynth | author = Moore, M. L.; Crossley, F. S. | title = Methyl Isothiocyanate | collvol = 3 | collvolpages = 599 | year = 1955 | prep = CV3P0599}}</ref> |
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It is also prepared via with the reaction of ] with ] followed by oxidation of the resulting ] with ]. A related method is useful to prepare this compound in the laboratory.<ref>{{ OrgSynth | author = Moore, M. L. | author2 = Crossley, F. S. | title = Methyl Isothiocyanate | year = 1941 | volume = 21 | pages = 81 | collvol = 3 | collvolpages = 599 | prep = CV3P0599 }}</ref> |
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MITC forms naturally upon the enzymatic degradation of glucocapparin, a modified sugar found in ]s. |
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MITC forms naturally upon the enzymatic degradation of glucocapparin, a ] found in ]s. |
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==Reactions== |
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==Reactions== |
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==Applications== |
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==Applications== |
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Solutions of MITC is used in agriculture as a soil ], mainly for protection against fungi and nematodes.<!-- can't figure this out: It is generated ''in situ'' from the reaction of metam sodium with water.--> |
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Solutions of MITC are used in agriculture as soil ]s, mainly for protection against fungi and nematodes.<ref>{{cite book |doi=10.1002/14356007.a17_125.pub2|chapter=Nematicides |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2008 |last1=Hartwig |first1=Jürgen |last2=Sommer |first2=Herbert |last3=Müller |first3=Franz |isbn=978-3527306732 }}</ref> |
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MITC is a building block for the synthesis of 1,3,4-thiadiazoles, which are ]s used as herbicides. Commercial products include "Spike", "Ustilan," and "Erbotan." Well known pharmaceuticals prepared using MITC include ] and ]. |
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MITC is a building block for the synthesis of 1,3,4-thiadiazoles, which are ]s used as herbicides. Commercial products include "Spike", "Ustilan," and "Erbotan." |
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Well known pharmaceuticals prepared using MITC include ] and ]. ] is a third example. |
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MITC is used in the ] patent (Ex2<ref>{{US patent|3417085}}</ref>), although the compound is question (Ex6) is with EITC. |
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==Safety== |
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==Safety== |
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MITC is a dangerous ] as well as being poisonous. |
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MITC is a dangerous ] as well as being poisonous. |
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==See also== |
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* ] |
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* ] |
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==References== |
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==References== |
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{{Reflist}} |
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<references/> |
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{{Cruciferous Biochemistry}} |
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