Benzo[b]thiophene-3-carbonyl chloride

Base Information

• Chemical Name: Benzo[b]thiophene-3-carbonyl chloride
• CAS No.: 39827-12-8
• Molecular Formula: C9H5 Cl O S
• Molecular Weight: 196.657
• Hs Code.: 29339900
• European Community (EC) Number: 692-237-7
• DSSTox Substance ID: DTXSID30379998
• Nikkaji Number: J89.313G
• Wikidata: Q82170025
• ChEMBL ID: CHEMBL3358214
• Mol file: 39827-12-8.mol

Synonyms:39827-12-8;Benzo[b]thiophene-3-carbonyl chloride;1-benzothiophene-3-carbonyl chloride;Benzothiophene-3-carbonyl chloride;CHEMBL3358214;Benzo[b]thiophene-3-carbonylchloride;benzothiophene-3-carboxylic acid chloride;SCHEMBL645673;DTXSID30379998;GSMXWLPUJAYDHX-UHFFFAOYSA-N;BDBM50037881;MFCD02682005;AKOS005172552;FS-5875;SB67090;1-benzo[b]thiophene-3-carbonyl chloride;FT-0607374;1-benzothiophene-3-carbonyl chloride, AldrichCPR;A824754;J-504230

Chemical Property of Benzo[b]thiophene-3-carbonyl chloride

Chemical Property:

• Vapor Pressure: 0.000636mmHg at 25°C
• Boiling Point: 309.5°Cat760mmHg
• Flash Point: 141°C
• PSA: 45.31000
• Density: 1.41g/cm³
• LogP: 3.28030
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 195.9749636
• Heavy Atom Count: 12
• Complexity: 195

Purity/Quality:

99% ^*data from raw suppliers

1-Benzothiophene-3-carbonylChloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C,Xi
• Statements: 34-36
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CS2)C(=O)Cl
• Uses: 1-Benzothiophene-3-Carbonyl Chloride was studied as for its potential as a novel CYP2A6 inhibitor to be used as a possible way to mediate nicotine metabolism.

Technology Process of Benzo[b]thiophene-3-carbonyl chloride

There total 4 articles about Benzo[b]thiophene-3-carbonyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

benzo[b]thiophene-3-carboxylic acid (5381-25-9) → benzothiophene-3-carbonyl chloride (39827-12-8)

Guidance literature:

With thionyl chloride; for 4h; Heating;

DOI:10.1002/jps.2600720228

Reference yield:

benzothiophene-3-carboxaldehyde (5381-20-4) → benzothiophene-3-carbonyl chloride (39827-12-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / acetone

2: (COCl)2; DMF / toluene / 3 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; N,N-dimethyl-formamide; In acetone; toluene;

DOI:10.1055/s-2002-35577

Reference yield:

3-Bromothianaphthene (7342-82-7) → benzothiophene-3-carbonyl chloride (39827-12-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: nBuLi / diethyl ether / -78 °C

1.2: diethyl ether / -78 °C

2.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / acetone

3.1: (COCl)2; DMF / toluene / 3 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; N,N-dimethyl-formamide; In diethyl ether; acetone; toluene;

DOI:10.1055/s-2002-35577

upstream raw materials:

benzo[b]thiophene-3-carboxylic acid

benzothiophene-3-carboxaldehyde

3-Bromothianaphthene

Downstream raw materials:

3-acetylbenzothiophene

N-phenylbenzo[b]thiophene-3-carboxamide

3-benzothiophenemethanamine

1-benzothiophene-3-yl isocyanate

Refernces

• 1、 Yamada, Takayuki,Shibata, Yu,Tanaka, Ken. "Formal Lossen Rearrangement/Alkenylation or Annulation Cascade of Heterole Carboxamides with Alkynes Catalyzed by CpRhIII Complexes with Pendant Amides". . p. 16022 - 16031. Retrieved 2019.
• 2、 Cachatra, Vasco,Carvalho, Sílvia,Chen, Li-Jun,Félix, Vítor,Gale, Philip A.,Goodfellow, Brian J.,Marques, Igor,Moiteiro, Cristina,Ryder, William G.. "Binding and Transport Properties of a Benzo[b]thiophene-Based Mono-(thio)urea Library". supporting information. . Retrieved 2022/02/02.
• 3、 Yu, Yongshi,Tazeem,Xu, Zhichao,Du, Liaoqi,Jin, Mengyu,Dong, Chune,Zhou, Hai-Bing,Wu, Shuwen. "Design and synthesis of heteroaromatic-based benzenesulfonamide derivatives as potent inhibitors of H5N1 influenza A virus". . p. 89 - 100. Retrieved 2019/01/30.