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

Isothiazolinone is a heterocyclic chemical compound related to isothiazole. It 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. It is a powerful biocide and preservative and is the major active ingredient in the commercial product KathonTM.

Uses

Used in Metal Working Fluids and Hydraulic Fluids:
Isothiazolinones are used as a high-performance biocide for preserving metal working fluids and hydraulic fluids. This is due to their ability to control the growth of fungi, bacteria, and algae in these fluids, which can cause corrosion and degradation of the fluids.
Used in Personal Care Formulations:
Isothiazolinones are used as a cost-effective antimicrobial for personal care formulations. They serve as a personal care preservative, preventing the growth of microorganisms that can spoil the product and cause skin irritation.
Used in Industrial Water Treatment:
Isothiazolinones are used as a high-performance industrial microbiocide for use in recirculating water cooling towers, wood, mold and mildew control, pulp and paper mills, and air washer systems. They are effective at very low use levels, making them a popular choice for industrial water treatment applications.
Used in Commercial Household and Cosmetics Products:
Isothiazolinones and their derivatives, such as 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one, are used together as preservatives in commercial households and cosmetics products. They are used in products like cleaners, shampoos, and washing materials to inhibit microbial activity that could lead to the product spoiling before the expected expiration date.
Used in Shampoo, Hand Sanitizer, and Lotions:
Isothiazolinones are used in these products as an inhibitor of microbial activity, ensuring the longevity and safety of the products for consumers.

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.

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

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

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.

STABLE COMPOSITIONS OF THIABENDAZOLE AND IODINE-CONTAINING FUNGICIDES

The present invention relates to stable compositions for the fungicidal equipment of thermoplastic polymers, in particular PVC, comprising thiabendazole, at least one iodine-containing fungicide and at least one epoxide and optionally further fungicidally active compounds, and also to methods for preparing these formulations and to uses thereof for the protection of thermoplastic polymers against attack and destruction by microorganisms. Moreover, the invention relates to mold-resistant PVC materials equipped with the compositions according to the invention.