26172-55-4

Basic information

• Product Name: Isothiazolinones
• Synonyms: 4-Isothiazolin-3-one,5-chloro-2-methyl-;5-chloro-2-methyl-3(2h)-isothiazolon;5-chloro-2-methyl-4-isothiazolin-3-on;5-chloro-2-methyl-isothiazolylthione-3;kathoncg5243;methylchloroisothiazoline;5-Chloro-2-methyl-Isothiazolone;5-CHLORO-2-METHYL-ISOTHIAZOL-3-ONE
• CAS NO: 26172-55-4
• Molecular Formula: C₄H₄ClNOS
• Molecular Weight: 149.6
• EINECS: 247-500-7
• Product Categories: Industrial/Fine Chemicals;INORGANIC & ORGANIC CHEMICALS;Biocide;Heterocycles;Inhibitors;Sulfur & Selenium Compounds;Bactericide and Algicide;Antibacterial agent;plantgrowth
• Mol File: 26172-55-4.mol
• Article Data: 29

Chemical Properties

• Melting Point: 42-45?C
• Boiling Point: 109.7°C
• Flash Point: 74.9 °C
• Appearance: Clear to yellow liquid
• Density: 1.25 (14% aq.)
• Vapor Pressure: 0.328mmHg at 25°C
• Refractive Index: n20/D 1.378
• Storage Temp.: Refrigerator
• PKA: -4.06±0.40(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Isothiazolinones(CAS DataBase Reference)
• NIST Chemistry Reference: Isothiazolinones(26172-55-4)
• EPA Substance Registry System: Isothiazolinones(26172-55-4)

Safety Data

• Hazard Codes: C,N,T,Xn
• Statements: 34-43-50-20/21/22-50/53-23/24/25-42/43
• Safety Statements: 26-36/37/39-45-60-61-24-28-36/37-23
• RIDADR: UN 1760 8/PG 2
• WGK Germany: 1
• RTECS: NX8156850
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 26172-55-4(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 26172-55-4 differently. You can refer to the following data:
1. Isothiazolinone is a heterocyclic chemical compound related to isothiazole. Isothiazolinone is an antimicrobial preservative that is often used to control fungi, bacteria, and algae. Since water-containing solutions are the breeding grounds for bacteria, isothiazolinone can easily be used in such solutions.
2. Methy1chloro-isothiazolinone (MCI) is contained, along with methylisothiazolinone (MI), in Kathon cosmetic grade (CG) and MCI/MI. It is irritant and sensitizer.

Applications

Although isothiazolinones have no direct applications, their derivatives such as 5-chloro-2-methyl-4-isothiazolin-3-on and 2-methyl-4-isothiazolin-3 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. Isothiazolinones is used in these products as an inhibitor of microbial activity that could lead to the product spoiling before the expected expiration date.

Safety Information

The recommended use of isothiazolinone products by the manufacturers used as wrinkle releaser is not harmful. However, allergy to skin is one of the most reported issue with isothiazolinone.

Chemical Properties

Liquid

Uses

Different sources of media describe the Uses of 26172-55-4 differently. You can refer to the following data:
1. Isocil(R) MW-14 is a high performance biocide for preserving metal working fluids, hydraulic fluids, polymer emulsions, pigment dispersions. Suggested applications: preservative concentrate. Very low level.
2. Isocil(R) PC is a cost-effective antimicrobial for personal care formulations. Suggested applications: personal care preservative.
3. Isocil(R) RW is 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.

Definition

ChEBI: A 1,2-thiazole that is 4-isothiazolin-3-one bearing a methyl group on the nitrogen atom and a chlorine at C-5. It is a powerful biocide and preservative and is the major active ingredient in the commercial product KathonTM.

InChI:InChI=1/C4H4ClNOS.ClH/c1-6-4(7)2-3(5)8-6;/h2H,1H3;1H

Synthetic route

N,N'-dimethyl-3,3'-dithiodipropionamide (999-72-4) → 5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4)

N,N'-dimethyl-3,3'-dithiodipropionamide (999-72-4) → 5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + 2-methyl-3-isothiazolone (2682-20-4)

Conditions	Yield
With thionyl chloride In 1,2-dichloro-ethane at 10℃; for 2h;	A 18% B 56%
With chlorine In ethyl acetate; acetonitrile at 5 - 10℃; for 1h; Solvent; Temperature; Overall yield = 85 percent;

N,N'-dimethyl-3,3'-dithiodipropionamide (999-72-4) → 5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + 4,5-Dichloro-2-methyl-3(2H)-isothiazolone (26542-23-4) + 2-methyl-3-isothiazolone (2682-20-4)

Conditions	Yield
With thionyl chloride In 1,2-dichloro-ethane	A 34% B 8% C 44%

3-oxo-2,3-dihydroisothiazole (1003-07-2) → 5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4)

1,2-dichloro-ethane (107-06-2) → 5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4)

Conditions	Yield
With sulfuryl dichloride

N-methyl-3-mercaptopropionamide (52334-99-3) → 5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + 2-methyl-3-isothiazolone (2682-20-4)

Conditions	Yield
With chlorine In N,N-dimethyl acetamide; chlorobenzene at 40 - 45℃; for 1h; Overall yield = 74 percent;
Stage #1: N-methyl-3-mercaptopropionamide With acetyl chloride In benzene at 25℃; for 0.666667h; Stage #2: With chlorine In benzene at 25℃; for 1h; Reagent/catalyst; Temperature; Solvent; Overall yield = 86.2 percent;

5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → [2-methyl-3-isothiazolon-5-yl]-(1-oxypyridin-2-yl)sulfide

Conditions	Yield
With sodium hydroxide In ethanol; water for 4h; pH=8.5;	70%

5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) → 5-chloro-N-methylisothiazol-3-amine

Conditions	Yield
Stage #1: 5-chloro-2-methyl-2H-isothiazol-3-one With trichlorophosphate Stage #2: With ammonia In acetonitrile at 0 - 20℃;	61%

5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + 2-methylpropan-2-thiol (75-66-1) → C8H14ClNOS2

Conditions	Yield
In sodium hydroxide; acidic aq. solution at 26℃; pH=4; Kinetics;

5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + sodium 2-mercaptobenzothiazole (2492-26-4) → [2-methyl-3-isothiazolon-5-yl]-(benzothiazol-2'-yl)sulfide

5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → [2-methyl-3-isothiazolon-5-yl]-(1-oxypyridin-2-yl)sulfide

Conditions	Yield
With sodium hydroxide In ethanol; chloroform	0.45 g (70%)

5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + disodium hydrogen phosphate + ethylenediamine tetraacid disodium salt + 2-methyl-3-isothiazolone (2682-20-4) + sodium phosphate → 2-octyl-isothiazol-3-one (26530-20-1)

Conditions	Yield
With sodium chloride
With sodium chloride

potassium phosphate + 5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + disodium hydrogen phosphate + 2-methyl-3-isothiazolone (2682-20-4) → 2-octyl-isothiazol-3-one (26530-20-1)

Conditions	Yield
With potassium chloride; sodium chloride
With potassium chloride; sodium chloride

5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) + disodium hydrogen phosphate + 2-methyl-3-isothiazolone (2682-20-4) + sodium phosphate → 2-octyl-isothiazol-3-one (26530-20-1)

Conditions	Yield
With sodium chloride
With sodium chloride

pyrrolidinedithiocarbamate (25769-03-3) + 5-chloro-2-methyl-2H-isothiazol-3-one (26172-55-4) → 2-Methyl-5-[N,N-tetramethylenethiocarbamoyl]thio-4-isothiazolin-3-one (79660-30-3)

Conditions	Yield
In ethanol; chloroform; di-isopropyl ether

Upstream product

• 1003-07-2 3-oxo-2,3-dihydroisothiazole 
• 52334-99-3 N-methyl-3-mercaptopropionamide 
• 107-06-2 1,2-dichloro-ethane 
• 999-72-4 N,N'-dimethyl-3,3'-dithiodipropionamide 

Downstream Products

• 26530-20-1 2-octyl-isothiazol-3-one 

Relevant articles and documents

Preparation method of 2-methyl-4-isothiazoline-3-one aqueous solution

The invention provides a preparation method of a 2-methyl-4-isothiazoline-3-one aqueous solution. The method comprises the following concrete steps: uniformly mixing N,N'-dimethyl-3,3'-dithiodipropionamide or N-methyl-3-mercaptopropionamide with a solvent; adding a halogenating agent into the mixed solution, and carrying out a halogenation ring closing reaction; filtering to obtain a product, washing a filter cake with ethyl acetate, and drying to obtain a 2-methyl-4-isothiazoline-3-one hydrochloride solid; and dissolving the 2-methyl-4-isothiazoline-3-one hydrochloride solid by using a sodiumcarbonate aqueous solution to obtain an aqueous solution of which the pH value is 5.0-7.0 and the mass fraction of 2-methyl-4-isothiazoline-3-one is 50%. According to the invention, the purity of the2-methyl-4-isothiazoline-3-one obtained by the method reaches 99.9% or above, and the content of 5-chlorine-2-methyl-4-isothiazoline-3-one can be controlled to be 100 ppm or below.

Pipeline type continuous production method of 3-isothiazolinone compound

The invention discloses a pipeline type continuous production method of a 3-isothiazolinone compound, which comprises the following steps: carrying out mixed reaction on a thioamide compound, a catalyst, a solvent and chlorine through a pipeline reactor system, and carrying out after-treatment after the reaction is completed to obtain the 3-isothiazolinone compound. According to the method, the defects of large occupied area, small productivity, low efficiency, high energy consumption and small safety coefficient caused by existing batch production of the 3-isothiazolinone compound are overcome; the invention provides a mode for continuously producing the 3-isothiazolinone compound, so that the reaction process is easy to control, energy consumption is reduced, the production efficiency and the safety coefficient of the production process are improved, and the process is an efficient and energy-saving safe production process.

MICROBICIDE

5-chloro-2-methyl-4-isothiazolin-3-yn as an active ingredient together with an, used in process for manufacturing a product of the co-organic solvent, in the residue and hydrolysates content of reduced for providing immunomodulated microbicidal, and ring alcoholic beverage group id amide 3-isothiazolone with a lactam-type including halogenation anger hydrogen salt neutralizing process device in manufacturing process, ring process moisture content as reaction solvent, the amount of acetic acid, ester and 0.1 weight % hereinafter, neutralizing step before the halogen anger hydrogen salt an ester of acetic acid dispersions obtained to filter out moisture content 0.1 weight % hereinafter in anger hydrogen salt halogen said hydrocarbon is added catalyst and a stabilizing agent to provide access to the filtration for solvent of exchanging and, moisture content collect the blood and to easily solvent exchange from process ring in addition 0.1 weight % hereinafter in an atmosphere of embodiment obtained with the device, which are in 5-chloro-2-methyl-4-isothiazoline-3-on as the active ingredient and, 10% weight concentration active ingredient when organic solvents and the Singer and total content of hydrolysate is microbicidal microbicides 200 888000000088 8 hereinafter.