399-73-5

Basic information

• Product Name: Benzothiazole, 6-fluoro-2-methyl- (7CI,8CI,9CI)
• Synonyms: Benzothiazole, 6-fluoro-2-methyl- (7CI,8CI,9CI);Benzothiazole, 6-fluoro-2-Methyl-;6-Fluoro-2-Methylbenzo[d]thiazole
• CAS NO: 399-73-5
• Molecular Formula: C₈H₆FNS
• Molecular Weight: 167.2033432
• Product Categories: BENZOTHIAZOLE
• Mol File: 399-73-5.mol

Chemical Properties

• Melting Point: 112-114 °C
• Boiling Point: 243.013°C at 760 mmHg
• Flash Point: 100.771°C
• Appearance: /
• Density: 1.319g/cm³
• Vapor Pressure: 0.051mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 1.48±0.10(Predicted)
• CAS DataBase Reference: Benzothiazole, 6-fluoro-2-methyl- (7CI,8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzothiazole, 6-fluoro-2-methyl- (7CI,8CI,9CI)(399-73-5)
• EPA Substance Registry System: Benzothiazole, 6-fluoro-2-methyl- (7CI,8CI,9CI)(399-73-5)

Safety Data

• Hazardous Substances Data: 399-73-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzothiazole, 6-fluoro-2-methyl(7CI,8CI,9CI) is used as a potential candidate for anti-cancer, anti-inflammatory, and anti-microbial agents due to its unique biological activities. The 6-fluoro-2-methyl substitution on the benzothiazole ring may enhance or modify these activities, making it a promising compound for further research and development in drug discovery and therapeutic applications.
Used in Chemical Industry:
In the chemical industry, Benzothiazole, 6-fluoro-2-methyl(7CI,8CI,9CI) may find applications in the synthesis of various chemical compounds and materials. Its unique structure and properties could be utilized in the development of new chemical processes, catalysts, or other specialty chemicals, contributing to advancements in the field.

InChI:InChI=1/C8H6FNS/c1-5-10-7-3-2-6(9)4-8(7)11-5/h2-4H,1H3

Upstream product

• 351-83-7 4'-fluoroacetanilide 
• 1009-22-9 N-(2-bromo-4-fluorophenyl)acetamide 
• 371-40-4 4-fluoroaniline 
• 29654-01-1 N-(2-iodo-4-fluorophenyl)acetamide 
• 399-36-0 N-(2,4-difluoro-phenyl)-acetamide 
• 367-25-9 2,4-difluorophenylamine 
• 141-82-2 malonic acid 
• 1544-68-9 4-fluorophenyl isothiocyanate 
• 351-84-8 N-(4-fluorophenyl)ethanethioamide 

Downstream Products

• 933749-06-5 6-fluorobenzo[d]thiazole-2-carbaldehyde 
• 157764-07-3 2-(6-fluorobenzo[d]thiazol-2-yl)acetonitrile 
• 33264-82-3 5-fluoro-2-aminobenzenethiol 

Relevant articles and documents

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 and antileishmanial activity of fluorinated rhodacyanine analogues: The ‘fluorine-walk’ analysis

In a search for potent antileishmanial drug candidates, eighteen rhodacyanine analogues bearing fluorine or perfluoroalkyl substituents at various positions were synthesized. These compounds were tested for their inhibitory activities against Leishmania martiniquensis and L. orientalis. This ‘fluorine-walk’ analysis revealed that the introduction of fluorine atom at C-5, 6, 5′, or 6′ on the benzothiazole units led to significant enhancement of the activity, correlating with the less negative reduction potentials of the fluorinated analogues confirmed by the electrochemical study. On the other hand, [sbnd]CF3 and [sbnd]OCF3 groups were found to have detrimental effects, which agreed with the poor aqueous solubility predicted by the in silico ADMET analysis. In addition, some of the analogues including the difluorinated species showed exceptional potency against the promastigote and axenic amastigote stages (IC50 = 40–85 nM), with the activities surpassing both amphotericin B and miltefosine.

Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization

A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.

Rational design and synthesis of 2-anilinopyridinyl-benzothiazole Schiff bases as antimitotic agents

Based on our previous results and literature precedence, a series of 2-anilinopyridinyl-benzothiazole Schiff bases were rationally designed by performing molecular modeling experiments on some selected molecules. The binding energies of the docked molecules were better than the E7010, and the Schiff base with trimethoxy group on benzothiazole moiety, 4y was the best. This was followed by the synthesis of a series of the designed molecules by a convenient synthetic route and evaluation of their anticancer potential. Most of the compounds have shown significant growth inhibition against the tested cell lines and the compound 4y exhibited good antiproliferative activity with a GI50 value of 3.8?μM specifically against the cell line DU145. In agreement with the docking results, 4y exerted cytotoxicity by the disruption of the microtubule dynamics by inhibiting tubulin polymerization via effective binding into colchicine domain, comparable to E7010. Detailed binding modes of 4y with colchicine binding site of tubulin were studied by molecular docking. Furthermore, 4y induced apoptosis as evidenced by biological studies like mitochondrial membrane potential, caspase-3, and Annexin V-FITC assays.

Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications

Recent efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective 3-[(benzothiazol-2-yl)methyl]indole-N-alkanoic acid aldose reductase inhibitors. The lead candidate, 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat, 9) inhibits aldose reductase with an IC50 of 5 nM, while being 5400 times less active against aldehyde reductase, a related enzyme involved in the detoxification of reactive aldehydes. It lowers nerve and lens sorbitol levels with ED50's of 1.9 and 4.5 mg/kg/d po, respectively, in the 5-day STZ-induced diabetic rat model. In a 3-month diabetic intervention model (1 month of diabetes followed by 2 months of drug treatment at 5 mg/kg/d po), it normalizes polyols and reduces the motor nerve conduction velocity deficit by 59% relative to diabetic controls. It has a favorable pharmacokinetic profile (F, 82%; t1/2, 5.6 h; Vd, 0.694 L/kg) with good drug penetration in target tissues (Cmax in sciatic nerve and eye are 2.36 and 1.45 μg equiv/g, respectively, when dosed with [14C] lidorestat at 10 mg/kg po).

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.