5-Chloro-2-methylbenzothiazole

Base Information

• Chemical Name: 5-Chloro-2-methylbenzothiazole
• CAS No.: 1006-99-1
• Molecular Formula: C8H6 Cl N S
• Molecular Weight: 183.661
• Hs Code.: 29335990
• European Community (EC) Number: 213-746-9
• NSC Number: 8453
• DSSTox Substance ID: DTXSID0061402
• Nikkaji Number: J37.320F
• Wikidata: Q72453750
• Mol file: 1006-99-1.mol

Synonyms:5-Chloro-2-methylbenzothiazole;1006-99-1;5-chloro-2-methylbenzo[d]thiazole;2-methyl-5-chlorobenzothiazole;5-Chloro-2-methyl-1,3-benzothiazole;BENZOTHIAZOLE, 5-CHLORO-2-METHYL-;USAF EK-P-4382;C8H6ClNS;5-Chloro-2-methyl-benzothiazole;NSC 8453;EINECS 213-746-9;BRN 0120802;2-Methyl-5-chloro-benzothiazole;MFCD00022881;4-27-00-01086 (Beilstein Handbook Reference);2-metyl-5-chloro-benzothiazole;NSC8453;5-CHLORO-2-METHYL BENZOTHIAZOLE;Cambridge id 5107825;SCHEMBL1049510;DTXSID0061402;WLN: T56 BN DSJ C1 HG;NSC-8453;STK396249;5-Chloro-2-methylbenzothiazole, 97%;AKOS000121462;5-Chloro-2-methyl-1,3-benzothiazole #;AC-15246;AS-12866;BP-12408;LS-40720;SY036182;CS-0037554;FT-0620269;EN300-21184;W-108946;F9995-1151;Z104493618

Chemical Property of 5-Chloro-2-methylbenzothiazole

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 0.000203mmHg at 25°C
• Melting Point: 65-70 ºC
• Refractive Index: 1.704
• Boiling Point: 147 °C / 15mmHg
• PKA: 1.14±0.10(Predicted)
• Flash Point: 121.2°C
• PSA: 41.13000
• Density: 1.365g/cm³
• LogP: 3.25810
• Storage Temp.: 2-8°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 182.9909481
• Heavy Atom Count: 11
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

5-Chloro-2-methylbenzothiazole ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2=C(S1)C=CC(=C2)Cl

Technology Process of 5-Chloro-2-methylbenzothiazole

There total 27 articles about 5-Chloro-2-methylbenzothiazole 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: 97.0%

5-chloro-2-iodoaniline (6828-35-9) + thioacetamide (62-55-5) → 2-methyl-5-chloro-benzothiazole (1006-99-1)

Guidance literature:

With calcium oxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; In N,N-dimethyl-formamide; at 60 ℃; for 1h;

DOI:10.1246/cl.1987.839

Reference yield: 94.0%

2-acetyl-4,5-dichloropyridazin-3(2H)-one (155164-63-9) + 4-chloro-2-aminobenzenethiol (1004-00-8) → 2-methyl-5-chloro-benzothiazole (1006-99-1)

Guidance literature:

In toluene; for 0.166667h; Reflux; Green chemistry;

DOI:10.1016/j.tet.2013.02.093

Reference yield: 93.0%

2-amino-4-chlorophenyl disulfide (29124-55-8) + ethanol (64-17-5) → 2-methyl-5-chloro-benzothiazole (1006-99-1)

Guidance literature:

With di-tert-butyl peroxide; at 150 ℃; for 6h; Sealed tube;

DOI:10.1016/j.tetlet.2019.05.021

upstream raw materials:

ethanol

N-(5-chloro-2-mercaptophenyl)acetamide

bis(2-nitro-4-chlorophenyl)disulfide

N-(3-chlorophenyl)ethanethioamide

Downstream raw materials:

Anhydro-2-methyl-5-chlor-3<3'-sulfopropyl>-benzthiazoliumhydroxid

19-oxaheptatriacontane

octadec-1-ene

1-pentadecene

Refernces

• 1、 Tian, Qingqiang,Luo, Wen,Gan, Zongjie,Li, Dan,Dai, Zeshu,Wang, Huajun,Wang, Xuetong,Yuan, Jianyong. "Eco-friendly syntheses of 2-substituted benzoxazoles and 2-substituted benzothiazoles from 2-aminophenols, 2-aminothiophenols and DMF derivatives in the presence of imidazolium chloride". . . Retrieved 2019.
• 2、 Lima, David B.,Penteado, Filipe,Vieira, Marcelo M.,Alves, Diego,Perin, Gelson,Santi, Claudio,Lenard?o, Eder J.. "α-Keto Acids as Acylating Agents in the Synthesis of 2-Substituted Benzothiazoles and Benzoselenazoles". . p. 3830 - 3836. Retrieved 2017.
• 3、 Padilha, Nathalia B.,Penteado, Filipe,Salom?o, Maria C.,Lopes, Eric F.,Bettanin, Luana,Hartwig, Daniela,Jacob, Raquel G.,Lenard?o, Eder J.. "Peroxide-mediated oxidative coupling of primary alcohols and disulfides: Synthesis of 2-substituted benzothiazoles". . p. 1587 - 1591. Retrieved 2019.
• 4、 Pan, Jun,Wang, Xinyan,Zhang, Yong,Buchwald, Stephen L.. "An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides". . p. 4974 - 4976. Retrieved 2011.
• 5、 Cai, Mingzhong,Hao, Wenyan,Huang, Wencheng,Ye, Qian. "Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles". . . Retrieved 2022/01/19.