1006-99-1

Basic information

• Product Name: 5-Chloro-2-methylbenzothiazole
• Synonyms: 5-CHLORO-2-METHYL-1,3-BENZOTHIAZOLE;5-CHLORO-2-METHYLBENZOTHIAZOLE;2-METHYL-5-CHLORO-BENZOTHIAZOLE;2-METYL-5-CHLORO-BENZOTHIAZOLE;5-chloro-2-methyl-benzothiazol;USAF ek-p-4382;usafek-p-4382;Benzothiazole, 5-chloro-2-methyl- (6CI,7CI,8CI,9CI)
• CAS NO: 1006-99-1
• Molecular Formula: C₈H₆ClNS
• Molecular Weight: 183.66
• EINECS: 213-746-9
• Product Categories: BENZOTHIAZOLE;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiazoles;ThiazolesHeterocyclic Building Blocks
• Mol File: 1006-99-1.mol

Chemical Properties

• Melting Point: 65-70 °C(lit.)
• Boiling Point: 147 °C / 15mmHg
• Flash Point: 85 °C
• Appearance: White to pale brown/Solid
• Density: 1.2741 (rough estimate)
• Vapor Pressure: 0.000203mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: 2-8°C
• PKA: 1.14±0.10(Predicted)
• CAS DataBase Reference: 5-Chloro-2-methylbenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-methylbenzothiazole(1006-99-1)
• EPA Substance Registry System: 5-Chloro-2-methylbenzothiazole(1006-99-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• WGK Germany: 3
• RTECS: DL3325000
• TSCA: Yes
• Hazardous Substances Data: 1006-99-1(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C8H6ClNS2/c1-11-8-10-6-4-5(9)2-3-7(6)12-8/h2-4H,1H3

Upstream product

• 29452-11-7 N-(3-chlorophenyl)ethanethioamide 
• 108-24-7 acetic anhydride 
• 615-48-5 2-amino-4-chloro-benzenethiol hydrochloride 
• 29124-55-8 2-amino-4-chlorophenyl disulfide 
• 64-17-5 ethanol 
• 827-66-7 N-(2-bromo-5-chlorophenyl)acetamide 
• 14091-36-2 N-(5-chloro-2-iodophenyl)acetamide 
• 5310-07-6 N-methyl-N-phenylthioacetamide 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 2466-76-4 N-Acetylimidazole 
• 127-19-5 N,N-dimethyl acetamide 
• 127-17-3 2-oxo-propionic acid 
• 17749-24-5 3-oxo-dithiobutyric acid methyl ester 
• 123-54-6 acetylacetone 

Downstream Products

• 65287-04-9 Anhydro-2-methyl-5-chlor-3<3'-sulfopropyl>-benzthiazoliumhydroxid 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 120-75-2 2-Methylbenzothiazole 
• 1351403-32-1 5-(sec-butoxy)-2-methylbenzothiazole 
• 1384553-93-8 1-(3,4-dimethoxyphenyl)-3-(2-methylbenzo[d]thiazol-5-yl)urea 
• 1230021-37-0 C₁₅H₁₂N₂O₂S 
• 90558-52-4 N,2-dimethylbenzo[d]thiazol-5-amine 
• 137449-44-6 5-chloro-2-trans-styryl-benzothiazole 
• 20061-46-5 2-methyl-1,3-benzothiazole-5-carbaldehyde 
• 90418-93-2 2-methyl-1,3-benzothiazole-5-carbonitrile 
• 13382-43-9 2-methyl-5-aminobenzothiazole 

Relevant articles and documents

Metal free montmorillonite KSF clay catalyzed practical synthesis of benzoxazoles and benzothiazoles under aerobic conditions

An efficient method for the synthesis of benzoxazoles and benzothiazoles via montmorillonite KSF clay catalyzed condensation reaction between 2-aminophenols or 2-aminothiophenols and β-diketones is reported. The efficiency of the reaction reflects from the wide substrate scope with electronic differentiation on aryls. The reaction is metal free and proceeds without the exclusion of air or moisture, and further the catalyst can be recycled up to 3–5 catalytic cycles.

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

A simple, economical and metal-free approach to the synthesis of 2-substituted benzoxazoles and 2-substituted benzothiazoles from 2-aminophenols, 2-aminothiophenols and DMF derivatives, only using imidazolium chloride (50% mmol) as promoter without any other additive, was reported. Various 2-substituted benzoxazoles and 2-substituted benzothiazoles were thus prepared in moderate to excellent yields.

Sodium dichloroiodate promoted C-C bond cleavage: An efficient synthesis of 1,3-Benzazoles via condensation of o -amino/mercaptan/hydroxyanilines with β -diketones

An efficient aqueous sodium dichloroiodate (NaICl 2) mediated protocol is developed for the synthesis of benzofused azoles by the cyclization of 2-amino anilines/thiophenols/phenols with β-diketone compounds. The reactions gave moderate to good yield of the corresponding 2-substituted benzimidazoles/benzothiazoles/benzoxazoles under mild conditions. This tandem process involved a C-C bond cleavage and C-N bond formation. Graphical Abstract?: SYNOPSIS A facile and single protocol for the synthesis of three versatile 1,3-benzazoles viz 2-substituted 1H-benzimidazoles, benzoxazoles and benzothiazoles from readily available starting materials, 1,3-diketones and corresponding o-amino anilines/thiophenols/phenols, by aqueous sodium dichloroiodate (NaICl 2) mediated C—C bond cleavage has been developed. The reaction provides a rapid access to these 1, 3-benzazoles in good yields, thus speeding up the drug discovery process.[Figure not available: see fulltext.].

α-Keto Acids as Acylating Agents in the Synthesis of 2-Substituted Benzothiazoles and Benzoselenazoles

Herein, we report the first decarboxylative oxidation of α-keto acids that is promoted by sodium metabisulfite (Na2S2O5) to obtain 2-substituted benzothiazoles and benzoselenazoles. Diaryl disulfides and diselenides were used as chalcogen sources, and the desired products were obtained in moderate to excellent yields. This protocol does not require an inert gas, transition metals, or harsh reaction conditions, and CO2 is released as an environmentally benign coproduct. The presence of Na2S2O5 was essential to guarantee that the reaction reached completion and afforded maximum product yields.

Eco-friendly atom-economical synthesis of 2-substituted-benzo[d]thiazoles and 2-substituted-benzo[d]oxazoles using 2-acylpyridazin-3(2H)-ones

Efficient and green syntheses of heterocycles are of great importance. In this work, we have demonstrated the synthesis of benzo[d]thiazoles and benzo[d]oxazoles using 2-acylpyridazin-3(2H)-ones as acyl transfer agents under transition-metal-free and eco-

Peroxide-mediated oxidative coupling of primary alcohols and disulfides: Synthesis of 2-substituted benzothiazoles

A peroxide-mediated protocol for the synthesis of 2-substituted benzothiazoles was developed, starting from bis(o-aminophenyl) disulfides and primary alcohols. Eleven differently 2-substituted benzothiazoles were prepared in moderate to excellent yields using di-tert-butyl peroxide (DTBP) as an oxidant.

Solid phase synthesis of benzothiazole and thiophene derivatives based on resin-bound cyclic malonic acid ester

A new method for the solid phase synthesis of benzothiazoles and 2-arylamino-3-carboxyl-4-hydroxy-5-arylthiophenes is described. Resin bound cyclic malonic acid ester was reacted with aryl isothiocyanates and then with bromine or α-bromoketones, followed by treatment with perchloric acid or sodium methoxide to afford substituted 2-methylbenzothiazoles or 2-arylamino-3-carboxyl-4-hydroxy-5-arylthiophenes, respectively, in high yields and purities.

An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides

A facile Pd-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) is described. This method allows convenient access to a variety of aryl, heteroaryl, and vinyl halides in good to excellent yields and with greatly simplified conditions relative to our previous report.

Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles

An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C–S coupling in DMF at 80 or 140 °C in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramolecular condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.

Synthesis method of benzothiazole compound

The invention relates to a novel process for synthesizing benzothiazole compounds, which comprises the following steps of: (1) heating and stirring orthoester, o-aminothiophenol and derivatives thereof to react, monitoring the reaction process by TLC, and obtaining crude benzothiazole compounds after the reaction is finished; and (2) distilling the crude benzothiazole compound obtained in the step (1) or recrystallizing by using a solvent, and filtering to obtain the benzothiazole compound. According to the method, no solvent is added in the reaction process, the separation and purification process is optimized, and green production of fine chemicals is effectively achieved; and no catalyst is added, the operation is simple, the reaction time is remarkably shortened, the production efficiency of the product is improved, and the yield can reach 79%-90%. The problems of environmental pollution, potential safety hazards, harm to human health, resource waste and the like caused by the solvent are fundamentally solved, and the method has extremely high green industrialization value.