Benzo[b]thiophene-3-acetic acid

Base Information

• Chemical Name: Benzo[b]thiophene-3-acetic acid
• CAS No.: 1131-09-5
• Molecular Formula: C10H8O2S
• Molecular Weight: 192.238
• Hs Code.: 2934999090
• European Community (EC) Number: 214-461-2
• NSC Number: 93635,18875
• UNII: N3GWR5VCX2
• DSSTox Substance ID: DTXSID70150283
• Nikkaji Number: J54.175C
• Wikidata: Q83016303
• ChEMBL ID: CHEMBL2138134
• Mol file: 1131-09-5.mol

Synonyms:1131-09-5;Benzo[b]thiophene-3-acetic acid;(Benzo[b]thiophen-3-yl)acetic acid;2-(benzo[b]thiophen-3-yl)acetic acid;2-(1-benzothiophen-3-yl)acetic acid;Acetic acid, 3-benzo(b)thienyl-;3-Benzo(b)thienylacetic acid;2-Benzo[b]thiophen-3-ylacetic acid;EINECS 214-461-2;Benzothiophene-3-acetic acid;1-benzothien-3-ylacetic acid;3-Benzo(b)thiopheneacetic acid;Benzo(b)thiophene-3-acetic acid;NSC 18875;NSC 93635;N3GWR5VCX2;thianaphthene-3-acetic acid;BRN 0143357;1-Benzothiophene-3-acetic acid;5-18-06-00447 (Beilstein Handbook Reference);NSC-18875;NSC-93635;3-Benzo[b]thienylacetic acid;WLN: T56 BSJ D1VQ;Acetic acid, 3-benzo[b]thienyl-;Benzo[b]thiophene-3-aceticacid;1-Benzothiophen-3-ylacetic acid;3-benzothienylacetic acid;Maybridge1_007369;UNII-N3GWR5VCX2;NCIOpen2_001520;Oprea1_783053;MLS000093716;3-benzo[b]thienyl acetic acid;SCHEMBL1233284;CHEMBL2138134;Benzp[b]thiophene-3-acetic acid;HMS562G21;DTXSID70150283;benzo[b]-thiophene-3-acetic acid;CHEBI:194621;HMS2174H22;HMS3446C14;Benzo[b]thiophen-3-yl-acetic acid;NSC18875;NSC93635;STR09444;CCG-52577;MFCD00051637;AKOS000282793;AM86322;PS-3254;SMR000029334;Benzo[b]thiophene-3-acetic acid, AldrichCPR;CS-0108787;FT-0622691;EN300-43083;F13984;SR-01000621926-2;Z432090858

Chemical Property of Benzo[b]thiophene-3-acetic acid

Chemical Property:

• Vapor Pressure: 2.07E-06mmHg at 25°C
• Melting Point: 82 °C
• Refractive Index: 1.688
• Boiling Point: 378.7 °C at 760 mmHg
• PKA: 4.23±0.30(Predicted)
• Flash Point: 182.9 °C
• PSA: 65.54000
• Density: 1.368 g/cm³
• LogP: 2.52840
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 192.02450067
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

98%,99%, ^*data from raw suppliers

Benzo[b]thiophene-3-acetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38-36
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CS2)CC(=O)O

Technology Process of Benzo[b]thiophene-3-acetic acid

There total 13 articles about Benzo[b]thiophene-3-acetic 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: 81.0%

carbon dioxide (124-38-9,18923-20-1) + C9H8N2S → benzo[b]thiophene-3-acetic acid (1131-09-5)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; caesium carbonate; cesium fluoride; In N,N-dimethyl-formamide; at 80 ℃; for 24h; under 760.051 Torr; chemoselective reaction;

DOI:10.1039/c8sc01299g

Reference yield: 66.0%

5-(3-benzo[b]thienyl)hexahydropyrimidine-2,4,6-trione → benzo[b]thiophene-3-acetic acid (1131-09-5)

Guidance literature:

With sodium hydroxide;

DOI:10.1023/A:1024781801125

Reference yield: 54.0%

3-(bromomethyl)benzothiophene (1196-19-6) + carbon monoxide (201230-82-2) → benzo[b]thiophene-3-acetic acid (1131-09-5)

Guidance literature:

With palladium hydroxide, 20 wt% on carbon; tetrabutylammomium bromide; water; In tetrahydrofuran; at 110 ℃; for 4h; under 7500.75 Torr; Sealed tube; Autoclave;

DOI:10.1021/acs.oprd.9b00402

upstream raw materials:

2-(benzo[b]thiophen-3-yl)acetonitrile

ethyl (2-chloroaceto)acetate

sodium thiophenolate

benzo[b]thiophen-3-ylmethyl-magnesium chloride

Downstream raw materials:

3-benzo-thienylacetamide

4-((E)-2-Benzo[b]thiophen-3-yl-vinyl)-2,6-dimethyl-phenol

3-phenylbutyric acid

methyl 3-benzothienylacetate

Refernces

• 1、 Gaertner. "-". . p. 2185,2187. Retrieved 1952.
• 2、 Wakuluk-Machado, Anne-Marie,Dewez, Damien F.,Baguia, Hajar,Imbratta, Miguel,Echeverria, Pierre-Georges,Evano, Gwilherm. "Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide". . p. 713 - 723. Retrieved 2020/02/04.
• 3、 Chapman,Scrowston,Westwood. "Pharmacologically active benzo[b]thiophen derivatives. 8. Benzo[b]thiophen analogues of tryptophan and alpha-methyltryptophan, and some of their 5-substituted derivatives.". . p. 1855 - 1858. Retrieved 2007/10/08.