6-Bromo-3-chloro-1-benzothiophene-2-carboxylic acid

Base Information

• Chemical Name: 6-Bromo-3-chloro-1-benzothiophene-2-carboxylic acid
• CAS No.: 438613-29-7
• Molecular Formula: C₉H₄BrClO₂S
• Molecular Weight: 291.553
• Hs Code.: 2934999090
• European Community (EC) Number: 673-149-8
• DSSTox Substance ID: DTXSID00357061
• Wikidata: Q82136773
• Mol file: 438613-29-7.mol

Synonyms:438613-29-7;6-bromo-3-chloro-1-benzothiophene-2-carboxylic acid;6-Bromo-3-chlorobenzo[b]thiophene-2-carboxylic acid;6-Bromo-3-chlorobenzo[b]thiophene-2-carboxylicacid;6-Bromo-3-Chlorobenzothiophene-2-Carboxylic Acid;C9H4BrClO2S;Benzo[b]thiophene-2-carboxylicacid, 6-bromo-3-chloro-;Cambridge id 7305320;AK-968/41017485;SCHEMBL18050231;DTXSID00357061;BBL016656;MFCD02090814;STK427450;AKOS000291390;SB67075;FT-0678484;Methyl 3,6-dimethyl-3-hydroxy-6-heptenoate;EN300-70128;F84470;A848180;Z228589152;6-Bromo-3-chloro-1-benzothiophene-2-carboxylic acid, AldrichCPR

Chemical Property of 6-Bromo-3-chloro-1-benzothiophene-2-carboxylic acid

Chemical Property:

• PSA: 65.54000
• LogP: 4.01540
• Storage Temp.: 2-8°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 289.88039
• Heavy Atom Count: 14
• Complexity: 251

Purity/Quality:

97% ^*data from raw suppliers

6-Bromo-3-chloro-1-benzothiophene-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)SC(=C2Cl)C(=O)O

Technology Process of 6-Bromo-3-chloro-1-benzothiophene-2-carboxylic acid

There total 3 articles about 6-Bromo-3-chloro-1-benzothiophene-2-carboxylic acid 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:

ethyl 6-bromo-3-chlorobenzo[b]thiophene-2-carboxylate (227803-28-3) + methyl 4-hydroxycinnamate (3943-97-3) → 6-bromo-3-chlorobenzo[b]thiophene-2-carboxylic acid (438613-29-7) + 6-bromo-3-chlorobenzo[b]thiophene + C18H11BrO5S + C21H17BrO5S

Guidance literature:

methyl 4-hydroxycinnamate; With tetrabutyl-ammonium chloride; potassium carbonate; In dimethyl sulfoxide; toluene; at 110 - 130 ℃; Inert atmosphere; Dean-Stark;

ethyl 6-bromo-3-chlorobenzo[b]thiophene-2-carboxylate; In dimethyl sulfoxide; toluene; at 15 - 85 ℃; for 40h; Inert atmosphere;

DOI:10.1021/acs.oprd.0c00076

Reference yield:

6-bromo-1-benzothiophene-2-carboxylic acid (19075-58-2) → 6-bromo-3-chlorobenzo[b]thiophene-2-carboxylic acid (438613-29-7)

Guidance literature:

6-bromo-1-benzothiophene-2-carboxylic acid; With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃; for 1h;

With N-chloro-succinimide; In tetrahydrofuran; at -70 ℃; for 0.5h;

Reference yield:

trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8) → 6-bromo-3-chlorobenzo[b]thiophene-2-carboxylic acid (438613-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine; thionyl chloride / chlorobenzene / 17.5 h / 65 - 125 °C / Inert atmosphere

1.2: -5 - 70 °C / Inert atmosphere

2.1: potassium carbonate; tetrabutyl-ammonium chloride / dimethyl sulfoxide; toluene / 110 - 130 °C / Inert atmosphere; Dean-Stark

2.2: 40 h / 15 - 85 °C / Inert atmosphere

With pyridine; thionyl chloride; tetrabutyl-ammonium chloride; potassium carbonate; In dimethyl sulfoxide; chlorobenzene; toluene;

DOI:10.1021/acs.oprd.0c00076

upstream raw materials:

6-bromo-1-benzothiophene-2-carboxylic acid

trans-4-bromocinnamic acid

ethyl 6-bromo-3-chlorobenzo[b]thiophene-2-carboxylate

methyl 4-hydroxycinnamate