2548-79-0

Basic information

• Product Name: 3-CHLORO-THIOBENZAMIDE
• Synonyms: 3-CHLOROBENZENE-1-CARBOTHIOAMIDE;3-Chlorobenzothioamide;3-CHLORO-THIOBENZAMIDE;3-CHLOROBENZENECARBOTHIOAMIDE
• CAS NO: 2548-79-0
• Molecular Formula: C₇H₆ClNS
• Molecular Weight: 171.65
• Mol File: 2548-79-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 289.5 °C at 760 mmHg
• Flash Point: 128.9 °C
• Appearance: /
• Density: 1.341 g/cm³
• Vapor Pressure: 0.0022mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.37±0.29(Predicted)
• CAS DataBase Reference: 3-CHLORO-THIOBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-THIOBENZAMIDE(2548-79-0)
• EPA Substance Registry System: 3-CHLORO-THIOBENZAMIDE(2548-79-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37
• RIDADR: UN2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2548-79-0(Hazardous Substances Data)

Usage

Uses

3-Chlorothiobenzamide is a thiobenzamide derivative with antibacterial activity.

InChI:InChI=1/C7H6ClNS/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H2,9,10)

Upstream product

• 587-04-2 m-Chlorobenzaldehyde 
• 34158-71-9 3-chlorobenzaldehyde oxime 
• 618-48-4 3-chlorobenzamide 
• 766-84-7 3-chloro-benzonitrile 
• 5909-67-1 tetramethyldiamidothiophosphoric acid 

Downstream Products

• 113984-97-7 N-(3-Chloro-thiobenzoyl)-acetamide 
• 27429-86-3 2-(3-chlorophenyl)-4,5-dihydro-1H-imidazole 
• 113985-00-5 1-Allyl-3-(3-chloro-thiobenzoyl)-thiourea 
• 113985-03-8 1-(3-Chloro-phenyl)-3-(3-chloro-thiobenzoyl)-urea 
• 113984-99-9 1-(3-Chloro-thiobenzoyl)-3-methyl-thiourea 
• 95211-54-4 3-[2-(3-Chloro-phenyl)-5-ethoxycarbonylmethyl-thiazol-4-yl]-propionic acid ethyl ester 
• 85558-99-2 3-(3-Chloro-phenyl)-[1,4,2]dithiazole-5-thione 
• 113985-02-7 1-(3-Chloro-thiobenzoyl)-3-phenyl-urea 
• 53514-99-1 [2-(3-chloro-phenyl)-4-(4-chloro-phenyl)-thiazol-5-yl]-acetic acid 
• 70650-90-7 3,5-bis-(3-chlorophenyl)-[1,2,4]thiadiazole 
• 144060-65-1 ethyl 2-(3-chlorophenyl)-4-hydroxy-1,3-thiazole-5-carboxylate 

Relevant articles and documents

Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions

Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.

Synthesis of imidazo[1,2-: C] thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides

Building new biological molecules is challenging. Herein, imidazo[1,2-c]thiazoles were synthesized as a new class of heterobicyclic analogs through Pd-catalyzed cascade bicyclization from isonitriles with thioamides. The bicyclic scaffolds were constructed by inserting three molecules of isonitrile into two molecules of thioamide and then cyclizing them in a one-pot procedure. In vitro antitumor studies of these new compounds were conducted by using the MTT assay, and compound 3c showed excellent inhibitory effects against HepG2 at 7.06 ± 0.68 μM.

Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.