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).

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] Methylisothiazolinone may cause respiratory irritation, skin sensitivities (including dermatitis), skin burns and eye damage according to peer-reviewed research and data from the European Chemicals Agency (ECHA) reported as part of the Environmental Working Group’s ‘Guide to Healthy Cleaning’. The American Contact Dermatitis Society named Methylisothiazolinone “allergen of the year” in 2013.^[6]

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
^ Why Methylisothiazolinone-Free Cleaning Products Matter

External links

[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

[AspenClean-6] Why Methylisothiazolinone-Free Cleaning Products Matter

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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).