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Chloromethylisothiazolinone is a heterocyclic chemical compound related to isothiazole.
Chloromethylisothiazolinone is an antimicrobial preservative that is often used to control fungi, bacteria, and algae.
Since water-containing solutions are the breeding grounds for bacteria, Chloromethylisothiazolinone can easily be used in such solutions.
CAS: 26172-55-4
MF: C4H4ClNOS
MW: 149.6
EINECS: 247-500-7
Synonyms
4-Isothiazolin-3-one,5-chloro-2-methyl-;5-chloro-2-methyl-3(2h)-isothiazolon;5-chloro-2-methyl-4-isothiazolin-3-on;Isothiazolinone;5-Chloro-2-methyl-4-isothiazolinone;5-CHLORIDE-2-METHYL-4-ISOTHIAZOLINE-3-KETONE;5-CHLORO-2-METHYL-4-ISOTHIAZOLIN-3-ONE (CMI);5-CHLORO-2-METHYL-3(2H)-ISOTHIAZOLONE MIXED WITH 2-METHYL-3(2H)ISOTHIAZOLONE
Chloromethylisothiazolinone is contained, along with methylisothiazolinone (MI), in Kathon cosmetic grade (CG) and MCI/MI.
Chloromethylisothiazolinone is irritant and sensitizer.
Chloromethylisothiazolinone bearing a methyl group on the nitrogen atom and a chlorine at C-5.
Chloromethylisothiazolinone is a powerful biocide and preservative and is the major active ingredient in the commercial product KathonTM.
Chloromethylisothiazolinone, also referred to as MCI, is the organic compound with the formula S(C2HCl)C(O)N(CH3).
Chloromethylisothiazolinone is a white solid that melts near room temperature.
Chloromethylisothiazolinone is an isothiazolinone, a class of heterocycles used as biocides.
Chloromethylisothiazolinone have an active sulphur moiety that is able to oxidize thiol-containing residues, thereby effectively killing most aerobic and anaerobic bacteria.
Chloromethylisothiazolinone is often used in combination with methylisothiazolinone, a mixture known as Kathon.
The isothiazolinones have attracted attention because they can cause contact dermatitis.
Chloromethylisothiazolinone is effective against gram-positive and gram-negative bacteria, yeast, and fungi.
Chloromethylisothiazolinone is a heterocyclic fungicide with strong inhibitory and killing effects on common bacteria, fungi, algae, etc.
Chloromethylisothiazolinone's boiling point is 200.2°C at 760 mmHg and its flash point is 74.9°C.
Chloromethylisothiazolinone's bactericidal principle mainly relies on the active part on the heterocyclic ring to destroy the DNA molecules in the bacterial cells, making the bacteria inactive.
Chloromethylisothiazolinone is miscible with chlorine and most anionic, cationic and non-ionic surfactants.
Chloromethylisothiazolinone is a highly water-soluble apoptotic agent and preservative with numerous applications.
Chloromethylisothiazolinone is used in anti-microbial coatings, latex formulations, hydraulic fracturing fluids, pesticides and cosmetics.
Chloromethylisothiazolinone in conjunction with 2-methyl-4-isothiazolin-3-one (MIT) is marketed as Kathon.
Chloromethylisothiazolinone is also an allergen.
Chloromethylisothiazolinone is active against gram-positive and gram-negative bacteria, yeasts and fungi.
Chloromethylisothiazolinone is believed to form mixed disulfides with protein thiol groups which then undergo thiol-disulfide exchange reactions to give mixed protein thiol disulfides leading to cell apoptosis and necrosis.
Chloromethylisothiazolinone Chemical Properties
Melting point: 42-45?C
Boiling point: 109.7°C
Density: 1.25 (14% aq.)
Refractive index: n20/D 1.378
Storage temp.: Refrigerator
Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
pka: -4.06±0.40(Predicted)
Form: Liquid
Color: White
Odor: Pungent aromatic odor
Stability: Stable. Incompatible with strong oxidizing agents.
InChI: InChI=1S/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3
InChIKey: DHNRXBZYEKSXIM-UHFFFAOYSA-N
LogP: 0.240 (est)
CAS DataBase Reference: 26172-55-4(CAS DataBase Reference)
NIST Chemistry Reference: Chloromethylisothiazolinone (26172-55-4)
EPA Substance Registry System: Chloromethylisothiazolinone (26172-55-4)
Applications
Although isothiazolinones have no direct applications, their derivatives such as Chloromethylisothiazolinone which are used together as preservatives in commercial households and cosmetics products, for instance, cleaners, shampoos, and washing materials.
Notably, various products that use isothiazolinones are in the market, including shampoo, hand sanitizer, and lotions.
Chloromethylisothiazolinone is used in these products as an inhibitor of microbial activity that could lead to the product spoiling before the expected expiration date.
Chloromethylisothiazolinone is a cost-effective antimicrobial for personal care formulations.
Suggested applications: personal care preservative.
Chloromethylisothiazolinoneis a high performance industrial microbiocide for use in recirculating water cooling towers, wood, mold and mildew control, pulp and paper mills, air washer systems.
Suggested applications: Industrial water treatment.
Very low use levels.
A Chloromethylisothiazolinone derivative as antimicrobial.
Chloromethylisothiazolinone was tested for inhibition of PCAF activity. 5-Chloroisothiazolinones showed the most potent inhibition of PCAF.
Chloromethylisothiazolinone is found in many water-based personal care products and cosmetics.
Chloromethylisothiazolinone was first used in cosmetics in the 1970s.
Chloromethylisothiazolinone is also used in glue production, detergents, paints, fuels, and other industrial processes.
Chloromethylisothiazolinone is known by the registered tradename Kathon CG when used in combination with methylisothiazolinone.
Chloromethylisothiazolinone may be used in combination with other preservatives including ethylparaben, benzalkonium chloride, bronopol and phenoxyethanol.
Hazards
Chloromethylisothiazolinone can cause allergic reactions in some people.
The first publication of the preservative as a contact allergen was in 1988.
Cases of photoaggravated allergic contact dermatitis, i.e. worsening of skin lesions after sun exposure, have also been reported.
In pure form or in high concentrations,Chloromethylisothiazolinone is a skin and membrane irritant and causes chemical burns.
In the United States, maximum authorized concentrations are 15 ppm in rinse-offs (of a mixture in the ratio 3:1 of 5-chloro-2-methylisothiazol 3(2H)-one and 2-methylisothiazol-3 (2H)-one).
In Canada, Chloromethylisothiazolinone may only be used in rinse-off products in combination with Chloromethylisothiazolinone, the total concentration of the combination may not exceed 15 ppm.
Chloromethylisothiazolinone is considered safe in the allowed amount in rinse-off products (0.01%) and safe in leave-in products when formulated to be non-sensitizing.
