Methylisothiazolinone

Methylisothiazolinone
Names
	Preferred IUPAC name 2-Methyl-1,2-thiazol-3(2H)-one
	Other names 2-Methylisothiazol-3(2H)-one; 2-Methyl-4-isothiazolin-3-one
Identifiers
CAS Number	2682-20-4 ;
3D model (JSmol)	Interactive image;
Abbreviations	MIT
Beilstein Reference	606203
ChEBI	CHEBI:53620 ;
ChEMBL	ChEMBL1620780;
ChemSpider	36393 ;
ECHA InfoCard	100.018.399
EC Number	220-239-6;
PubChem CID	39800;
UNII	229D0E1QFA ;
CompTox Dashboard (EPA)	DTXSID2034259 ;
	InChI InChI=1S/C4H5NOS/c1-5-4(6)2-3-7-5/h2-3H,1H3 Key: BEGLCMHJXHIJLR-UHFFFAOYSA-N ; InChI=1/C4H5NOS/c1-5-4(6)2-3-7-5/h2-3H,1H3;
	SMILES O=C1/C=C\SN1C;
Properties
Chemical formula	C4H5NOS
Molar mass	115.1 g/mol
Appearance	white solid
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H311, H314, H317, H318, H330, H400, H410
GHS precautionary statements	P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+310, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P320, P321, P322, P330, P333+313, P361, P363, P391
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Methylisothiazolinone, MIT, or MI, is the organic compound with the formula S(CH)₂C(O)NCH₃. It is a white solid. Isothiazolinones, a class of heterocycles, are used as biocides in numerous personal care products and other industrial applications. MIT and related compounds have attracted much attention for their allergenic properties, e.g. contact dermatitis.[1]

It is prepared by cyclization of cis-N-methyl-3-thiocyanoacrylamide:[2]

NCSCH=CHC(O)NHCH₃ → SCH=CHC(O)NCH₃ + HCN

Safety

MIT is allergenic and cytotoxic, and this has led to some concern over its use.[3] It has attracted concern in the U.S. and in Europe.[4][5]

References

Silva, Vânia; Silva, Cátia; Soares, Pedro; Garrido, E. Manuela; Borges, Fernanda; Garrido, Jorge (2020). "Isothiazolinone Biocides: Chemistry, Biological, and Toxicity Profiles". Molecules. 25 (4): 991. doi:10.3390/molecules25040991. PMC 7070760. PMID 32102175.
Crow, W. D.; Leonard, Nelson J. (1965). "3-Isothiazolone-cis-3-Thiocyanoacrylamide Equilibria1,2". The Journal of Organic Chemistry. 30 (8): 2660–2665. doi:10.1021/jo01019a037.
Castanedo-Tardana, M. P.; Zug, K. A. (2013). "Methylisothiazolinone". Dermatitis : Contact, Atopic, Occupational, Drug. 24 (1): 2–6. doi:10.1097/DER.0b013e31827edc73. PMID 23340392. S2CID 220573338.
MCI/MI/BIT Call To Action!
European Scientific Committee on Cosmetic Products and Non-food Products Intended for Consumers (SCCNFP), adopted 2004

External links

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[rev-1] Silva, Vânia; Silva, Cátia; Soares, Pedro; Garrido, E. Manuela; Borges, Fernanda; Garrido, Jorge (2020). "Isothiazolinone Biocides: Chemistry, Biological, and Toxicity Profiles". Molecules. 25 (4): 991. doi:10.3390/molecules25040991. PMC 7070760. PMID 32102175.

[2] Crow, W. D.; Leonard, Nelson J. (1965). "3-Isothiazolone-cis-3-Thiocyanoacrylamide Equilibria1,2". The Journal of Organic Chemistry. 30 (8): 2660–2665. doi:10.1021/jo01019a037.

[Castanedo-3] Castanedo-Tardana, M. P.; Zug, K. A. (2013). "Methylisothiazolinone". Dermatitis : Contact, Atopic, Occupational, Drug. 24 (1): 2–6. doi:10.1097/DER.0b013e31827edc73. PMID 23340392. S2CID 220573338.

[4] MCI/MI/BIT Call To Action!

[SCCNFP-5] European Scientific Committee on Cosmetic Products and Non-food Products Intended for Consumers (SCCNFP), adopted 2004