62524-21-4

Basic information

• Product Name: 3-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID HYDRAZIDE
• Synonyms: BUTTPARK 96\04-82;AKOS BBS-00007328;AKOS BBB/117;AKOS AU36-M201;3-CHLORO-1-BENZOTHIOPHENE-2-CARBOHYDRAZIDE;3-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID HYDRAZIDE;3-CHLOROBENZO[B]THIOPHENE-2-CARBOHYDRAZIDE;3-Chloro-benzo[b]thiophene-2-carboxylic acid hydrazide ,97%
• CAS NO: 62524-21-4
• Molecular Formula: C₉H₇ClN₂OS
• Molecular Weight: 226.68
• Mol File: 62524-21-4.mol

Chemical Properties

• Melting Point: 181 °C
• Appearance: /
• Density: 1.486 g/cm³
• Refractive Index: 1.714
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID HYDRAZIDE(62524-21-4)
• EPA Substance Registry System: 3-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID HYDRAZIDE(62524-21-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 62524-21-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to light yellow solid

InChI:InChI=1/C9H7ClN2OS/c10-7-5-3-1-2-4-6(5)14-8(7)9(13)12-11/h1-4H,11H2,(H,12,13)

Upstream product

• 21211-07-4 3-chlorobenzo[b]thiophene-2-carboxylic acid methyl ester 
• 21815-91-8 3-chlorobenzo[b]thiophen-2-carbonyl chloride 
• 621-82-9 Cinnamic acid 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 144605-10-7 3-Chloro-benzo[b]thiophene-2-carboxylic acid [1-(4-hydroxy-phenyl)-eth-(E)-ylidene]-hydrazide 
• 298230-78-1 C₁₆H₁₀ClFN₂OS 
• 324561-36-6 C₁₆H₁₀Cl₂N₂OS 
• 346718-75-0 C₁₇H₁₃ClN₂O₂S 
• 675835-10-6 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-phenyl-1,3,4-oxadiazole 
• 333397-35-6 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 1257983-63-3 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-phenyl-2,3-dihydro-1,3,4-oxadiazole 
• 1257983-64-4 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-(4-fluorophenyl)-2,3-dihydro-1,3,4-oxadiazole 
• 1257983-66-6 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-(2-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole 
• 1257983-67-7 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-(4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole 
• 1257983-68-8 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-(3-nitrophenyl)-2,3-dihydro-1,3,4-oxadiazole 
• 1257983-69-9 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole 
• 1257983-70-2 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-(3-methoxy-4-hydroxyphenyl)-2,3-dihydro-1,3,4-oxadiazole 
• 540519-97-9 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole 

Relevant articles and documents

Targeting malaria and leishmaniasis: Synthesis and pharmacological evaluation of novel pyrazole-1,3,4-oxadiazole hybrids. Part II

In continuance with earlier reported work, an extension has been carried out by the same research group. Mulling over the ongoing condition of resistance to existing antimalarial agents, we had reported synthesis and antimalarial activity of certain pyrazole-1,3,4-oxadiazole hybrid compounds. Bearing previous results in mind, our research group ideated to design and synthesize some more derivatives with varied substitutions of acetophenone and hydrazide. Following this, derivatives 5a–r were synthesized and tested for antimalarial efficacy by schizont maturation inhibition assay. Further, depending on the literature support and results of our previous series, certain potent compounds (5f, 5n and 5r) were subjected to Falcipain-2 inhibitory assay. Results obtained for these particular compounds further strengthened our hypothesis. Here, in this series, compound 5f having unsubstituted acetophenone part and a furan moiety linked to oxadiazole ring emerged as the most potent compound and results were found to be comparable to that of the most potent compound (indole bearing) of previous series. Additionally, depending on the available literature, compounds (5a–r) were tested for their antileishmanial potential. Compounds 5a, 5c and 5r demonstrated dose-dependent killing of the promastigotes. Their IC50 values were found to be 33.3 ± 1.68, 40.1 ± 1.0 and 19.0 ± 1.47 μg/mL respectively. These compounds (5a, 5c and 5r) also had effects on amastigote infectivity with IC50 of 44.2 ± 2.72, 66.8 ± 2.05 and 73.1 ± 1.69 μg/mL respectively. Further target validation was done using molecular docking studies. Acute oral toxicity studies for most active compounds were also performed.

Synthesis and pharmacological properties of some new 2-substituted benzo [b] thiophenes

3-Chlorobenzothiophene-2-carbonyl chloride 1 was treated with l-(aminomethyl) cyclohexylacetic acid in acetone to get compound 2, compound 1 was also reacted with substituted 2-aminobenzothiazoles, carbohydrizeds, anilines and pyrazole to get 3a-d, 4a-d,

Synthesis and antimicrobial activity of some new 5-(3-chloro-1- benzothiophen-2-YL)-1,3,4-oxadiazole-2-thiol and their derivatives

3-Chloro-1-benzothiophene-2-carbonylchloride 1 was made to reacts with hydrazine hydrate afforded 3-chloro-1-benothiophene-2-carbohydrazide 2 in good yield. 5-(3-chloro-1-benzothiophen-2-yl)-1,3,4-oxadiazole-2-thiol 4 was synthesized from 3-chloro- 1-benz

Synthesis and biological activity of some more heterocyclic compounds containing benzothiophene moiety

3-Chloro-1-benzothiophene-2-carbonylchloride 1 was allowed to react with hydrazine hydrate to give carbohydrazide 2. The reaction of 3-chloro-1- benzothiophene-2-carbohydrazide 2 with potassium thiocyanate gave compound 3, which was cyclized to form thioxotetrahydropyrimidine 4, thiazoles 5a-e, triazoles 7a-e and oxadiazoles 10a-h. The structures of all the synthesized compounds were confirmed by spectral data and have been screened for antimicrobial, analgesic and anthelmintic activities.

Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents

Some new 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-substituted phenyl-2,3-dihydro-1,3,4-oxadiazoles and 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5- substituted phenyl-1,3,4-oxadiazoles have been synthesized and evaluated for antimicrobial activity. Init

Synthesis, antimicrobial, and anthelmintic activities of some new 3-chlorobenzothiophene-2-carbonylchloride derivatives

3-Chlorobenzothiophene-2-carbonylchloride 1 was prepared from cinnamic acid and then converted into the acid hydrazide 2. Reaction of 3-chloro-1- benzothiophene-2-carbohydrazide 2 with the appropriate isothiocyanate yielded the substituted thiosemicarbazi

Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives

Benzo[b]thiophene molecules are found to be important tools in synthetic medicinal chemistry. They are of current interest due to their wide spectrum of pharmacological properties. In view of the biological activities of benzo[b]thiophene containing molecules, in this present research work, we propose the synthesis of some new benzo[b]thiophene derivatives such as thiadiazoles, oxadiazoles, pyrazolin & diaryl pyrazoles starting from 3-chlorobenzo[b]thiophene-2-carboxyl chloride. These newly synthesized compounds were characterized by elemental analyses, I.R, NMR and Mass spectral studies. Some of the selected compounds were screened for their antibacterial, antifungal and anti-inflammatory studies. Many of the molecules were found to be potent.

Synthesis of benzo[b]thiophene substituted carbamates, ureas, semicarbazides, and pyrazoles and their antimicrobial and analgesic activity

2-Azidocarbonyl-3-chlorobenzo[b]thiophene 3 was obtained from 3-chloro-benzo[b]thiophene-2-carbonyl chloride 1 and 3-chloro-benzo[b]thiophene- 2-carboxy hydrazide 2. The compound 3 on Curtius rearrangement with various alcohols, amines, and hydrazines afforded the corresponding carbamates 4a-b, ureas 5a-j, and semicarbazides 6a-g, respectively. Compound 2 was also utilized for the synthesis of pyrazoles 7a-c by treatment with various chalcones. The structures of the newly synthesized compounds were elucidated on the basis of IR, 1H NMR, and mass spectral data and have been screened for antimicrobial and analgesic activities.

Synthesis of oxadiazoles, thiadiazoles and triazoles derived from benzo[b]thiophene

In this work 3-chloro-2-chlorocarbonylbenzo[b]thiophene (1) was prepared from cinnamic acid and then converted into the acid hydrazide 2. The azomethines 3a-e were prepared from the corresponding aryl aldehydes and the acid hydrazide 2. Treatment of compo

Benzo[b]thiophenes, Part I: Synthesis and antimicrobial activity of benzo[b]thienyl-1,3,4-oxadiazole, -1,2,4-triazoline, and -thiazoline derivatives

Four new series of benzo[b]thiophene derivatives bearing various thiosemicarbazide, 1,3,4-oxadiazole, 1,2,4-triazoline, and thiazoline moieties have been synthesized and evaluated for antimicrobial activity.