5-Chloro-2-methyl-4-isothiazolin-3-one

Base Information

• Chemical Name: 5-Chloro-2-methyl-4-isothiazolin-3-one
• CAS No.: 26172-55-4
• Deprecated CAS: 137662-59-0,137086-87-4,137086-87-4
• Molecular Formula: C4H4ClNOS
• Molecular Weight: 149.601
• Hs Code.: 2934999090
• European Community (EC) Number: 247-500-7
• UNII: DEL7T5QRPN
• DSSTox Substance ID: DTXSID9034286
• Nikkaji Number: J40.688K
• Wikipedia: Methylchloroisothiazolinone
• Wikidata: Q204121
• RXCUI: 1367119
• Metabolomics Workbench ID: 58674
• ChEMBL ID: CHEMBL1738962
• Mol file: 26172-55-4.mol

Synonyms:5-chloro-2-methyl-4-isothiazolin-3-one;5-chloro-2-methyl-4-isothiazolin-3-one hydrochloride;5-chloro-2-methylisothiazolin-3-one;5-chloro-N-methylisothiazolone;5243-K-Cg;methylchloro-isothiazolinone;methylchloroisothiazolinone

Chemical Property of 5-Chloro-2-methyl-4-isothiazolin-3-one

Chemical Property:

• Appearance/Colour: Clear to yellow liquid
• Vapor Pressure: 0.328mmHg at 25°C
• Melting Point: 42-45?C
• Refractive Index: n20/D 1.378
• Boiling Point: 200.2 °C at 760 mmHg
• PKA: -4.06±0.40(Predicted)
• Flash Point: 74.9 °C
• PSA: 50.24000
• Density: 1.51 g/cm³
• LogP: 1.10020
• Storage Temp.: Refrigerator
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 148.9702126
• Heavy Atom Count: 8
• Complexity: 156

Purity/Quality:

≥14% ^*data from raw suppliers

5-Chloro-2-methyl-3-isothiazolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,N,T
• 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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: CN1C(=O)C=C(S1)Cl
• Description: 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. Methy1chloro-isothiazolinone (MCI) is contained, along with methylisothiazolinone (MI), in Kathon cosmetic grade (CG) and MCI/MI. It is irritant and sensitizer.
• Uses: 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. Isocil(R) PC is a cost-effective antimicrobial for personal care formulations. Suggested applications: personal care preservative. 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.

Technology Process of 5-Chloro-2-methyl-4-isothiazolin-3-one

There total 7 articles about 5-Chloro-2-methyl-4-isothiazolin-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

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

Guidance literature:

With chlorine; potassium iodide; In ethyl acetate; at 40 - 55 ℃; for 0.25h;

Reference yield: 56.0%

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)

Guidance literature:

With thionyl chloride; In 1,2-dichloro-ethane; at 10 ℃; for 2h;

DOI:10.1016/j.tet.2003.09.064

Reference yield: 8.0%

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)

Guidance literature:

With thionyl chloride; In 1,2-dichloro-ethane;

DOI:10.1016/j.tet.2003.09.064

upstream raw materials:

N,N'-dimethyl-3,3'-dithiodipropionamide

3-oxo-2,3-dihydroisothiazole

1,2-dichloro-ethane

N-methyl-3-mercaptopropionamide

Downstream raw materials:

2-octyl-isothiazol-3-one

Refernces

• 1、 -. "Preparation method of 3-isothiazolinone compound". Paragraph 0033-0039. . Retrieved 2020/12/31.
• 2、 -. "MICROBICIDE". Paragraph 0065; 0067. . Retrieved 2016/12/07.