Methylisothiazolinone

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]

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
3D model (JSmol)
Abbreviations MIT
606203
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.018.399
EC Number
  • 220-239-6
UNII
Properties
C4H5NOS
Molar mass 115.1 g/mol
Appearance white solid
Hazards
GHS pictograms
GHS Signal word Danger
H301, H311, H314, H317, H318, H330, H400, H410
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).
Y verify (what is YN ?)
Infobox references

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

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

Safety
Main article: Isothiazolinone

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
  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.
  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!
  5. European Scientific Committee on Cosmetic Products and Non-food Products Intended for Consumers (SCCNFP), adopted 2004
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.