7312-10-9

Basic information

• Product Name: 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID
• Synonyms: 5-BROMO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID;5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID;5-bromo-1,3-benzothiazole-2-carboxylic acid;5-Bromo-1-benzothiophene-2-carboxylic acid, 5-Bromo-2-carboxy-1-benzothiophene
• CAS NO: 7312-10-9
• Molecular Formula: C₉H₅BrO₂S
• Molecular Weight: 257.1
• Product Categories: Carboxylic Acids;Thiophenes & Benzothiophenes;Carboxylic Acids;Thiophenes & Benzothiophenes
• Mol File: 7312-10-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 230-234°C
• Boiling Point: 429.7 °C at 760 mmHg
• Flash Point: 213.7 °C
• Appearance: /
• Density: 1.813 g/cm³
• Vapor Pressure: 3.8E-08mmHg at 25°C
• Refractive Index: 1.738
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.29±0.30(Predicted)
• CAS DataBase Reference: 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID(7312-10-9)
• EPA Substance Registry System: 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID(7312-10-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 7312-10-9(Hazardous Substances Data)

Usage

General Description

5-Bromo-1-benzothiophene-2-carboxylic Acid is a sophisticated chemical compound known for its utility in scientific research, primarily within the discipline of chemistry. Its systematic name is 5-Bromo-benzo[b]thiophene-2-carboxylic acid, and it has a molecular weight of 277.07 g/mol. It falls under the category of heterocyclic compounds, specifically possessing a benzothiophene structure. Its unique structure of a fused aromatic ring makes it interesting for the studies probing the influence of bromine-substitution on chemical properties and reactivity. Furthermore, its carboxylic acid group expands its utility, such as in the production of various derivatives for different chemical reactions. However, it is deemed to require expert handling due to its potentially hazardous nature.

InChI:InChI=1/C9H5BrO2S/c10-6-1-2-7-5(3-6)4-8(13-7)9(11)12/h1-4H,(H,11,12)

Upstream product

• 101774-45-2 (4-bromo-2-cyano-phenylsulfanyl)-acetic acid 
• 7312-11-0 5-bromo-1-benzothiophene-2-carboxylic acid methyl ester 
• 1423-64-9 1-(5-bromobenzo[b]thiophen-2-yl)ethan-1-one 
• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 4923-87-9 5-bromobenzo[b]thiophene 
• 124-38-9 carbon dioxide 

Downstream Products

• 644988-73-8 5-bromo-benzo[b]thiophene-2-carboxylic acid {4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butyl}-amide 
• 644988-72-7 5-bromo-benzo[b]thiophene-2-carboxylic acid {4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-amide 
• 13771-68-1 5-bromobenzo[b]thiophene-2-carboxylic acid ethyl ester 
• 105191-14-8 5-Cyanbenzothiophen-2-carbonsaeure-ethylester 
• 7312-14-3 5-bromobenzo[b]thiophene-2-carbonyl chloride 
• 1093631-53-8 5-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-benzothiophene-2-carboxylic acid 
• 1236000-73-9 5-bromo-N-methyI-N-({4-[(trifluoromethyl)oxy]phenyl}methyl)-1-benzothiophene-2-carboxamide 
• 13771-72-7 (5-bromobenzo[b]thiophen-2-yl)methanol 

Relevant articles and documents

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

Design, synthesis, and biological evaluation of benzo[b]thiophene 1,1-dioxide derivatives as potent STAT3 inhibitors

As a member of the signal transducer and activator of transcription (STAT) family, STAT3 plays a critical role in several biological pathways such as cell proliferation, migration, survival, and differentiation. Due to abnormal continuous activation in tumors, inhibition of STAT3 has emerged as an attractive approach for the treatment of various cancer cells. Herein, we report a series of novel STAT3 inhibitors based on benzo[b]thiophene 1,1-dioxide scaffold and evaluated their anticancer potency. Among them, compound 8b exhibited the best activity against cancer cells. Compound 8b induced apoptosis and blocked the cell cycle. Meanwhile, 8b reduced intracellular ROS content and caused the loss of mitochondrial membrane potential. Further research revealed that 8b significantly blocked STAT3 phosphorylation and STAT3-dependent dual-luciferase reporter gene experiments showed that compound 8b has a marked inhibition of STAT3-mediated Firefly luciferase activity. Molecular modeling studies revealed compound 8b occupied the pocket well with the SH2 domain in a favorable conformation.

Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?

The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 μM and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 μM). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 ± 0.37 μM). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.