Methyl benzo[b]thiophene-2-carboxylate

Base Information

• Chemical Name: Methyl benzo[b]thiophene-2-carboxylate
• CAS No.: 22913-24-2
• Molecular Formula: C10H8O2S
• Molecular Weight: 192.238
• Hs Code.: 2934999090
• European Community (EC) Number: 625-266-0
• DSSTox Substance ID: DTXSID50384160
• Nikkaji Number: J83.234K
• Wikidata: Q72487996
• ChEMBL ID: CHEMBL560931
• Mol file: 22913-24-2.mol

Synonyms:Methyl benzo[b]thiophene-2-carboxylate;22913-24-2;methyl 1-benzothiophene-2-carboxylate;Benzo[b]thiophene-2-carboxylic acid methyl ester;Benzo[b]thiophene-2-carboxylic acid, methyl ester;MFCD00067791;Methyl benzo(b)thiophene-2-carboxylate;Benzo(b)thiophene-2-carboxylic acid methyl ester;Maybridge1_001812;SCHEMBL700108;CHEMBL560931;HMS546K08;DTXSID50384160;GEO-00287;STK736357;AKOS000280413;DS-4162;SY006828;CS-0043114;FT-0628702;Methyl benzo[b]thiophene-2-carboxylate, 97%;EN300-193090;W-200236

Chemical Property of Methyl benzo[b]thiophene-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 70-74 °C
• Refractive Index: 1.638
• Boiling Point: 304.586 °C at 760 mmHg
• Flash Point: 138.009 °C
• PSA: 54.54000
• Density: 1.274 g/cm³
• LogP: 2.68790
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 192.02450067
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

99%, ^*data from raw suppliers

Methyl benzo[b]thiophene-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC2=CC=CC=C2S1

Technology Process of Methyl benzo[b]thiophene-2-carboxylate

There total 36 articles about Methyl benzo[b]thiophene-2-carboxylate 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: 98.0%

methanol (67-56-1) + benzo[b]thiophene-2-carboxylic acid (6314-28-9) → methyl benzo[b]thiophene-2-carboxylate (22913-24-2)

Guidance literature:

With chloro-trimethyl-silane;

DOI:10.1055/s-2004-822891

Reference yield: 95.0%

carbon dioxide (124-38-9,18923-20-1) + Benzo[b]thiophene (95-15-8,11095-43-5) + methyl iodide (74-88-4) → methyl benzo[b]thiophene-2-carboxylate (22913-24-2)

Guidance literature:

carbon dioxide; Benzo[b]thiophene; With 18-crown-6 ether; cesium fluoride; lithium tert-butoxide; at 160 ℃; for 15h; under 760.051 Torr; Inert atmosphere; Sealed tube;

methyl iodide; at 60 ℃; for 2h; Reagent/catalyst;

DOI:10.1002/chem.201805926

Reference yield: 95.0%

methanol (67-56-1) + benzothiophene-2-carboxaldehyde (3541-37-5) → methyl benzo[b]thiophene-2-carboxylate (22913-24-2)

Guidance literature:

With 2,2':6,2''-terpyridine; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate; sodium hydroxide; at 90 ℃; for 24h; chemoselective reaction; Green chemistry;

DOI:10.1039/c6sc00145a

upstream raw materials:

diazomethane

benzo[b]thiophene-2-carboxylic acid

methanol

2-chlorobenzo[b]thiophene

Downstream raw materials:

benzothiophene-2-methanol

2-Methylbenzothiophene

benzo[b]thiophene-2-carboxylic acid hydrazide

benzo[b]thiophene-2-carboxylic acid-(2-chloro-anilide)

Refernces

• 1、 Li, Wen-Zhen,Xi, Hui-Zhi,Wang, Yi-Jie,Ma, Hong-Bo,Cheng, Zhi-Qiang,Yang, Yu,Wu, Meng-Ling,Liu, Ting-Mei,Yang, Wen,Wang, Qin,Liao, Meng-Ya,Xia, Yong,Zhang, Yi-Wen. "Design, synthesis, and biological evaluation of benzo[b]thiophene 1,1-dioxide derivatives as potent STAT3 inhibitors". . p. 835 - 849. Retrieved 2021/09/02.
• 2、 Lee, Mijung,Hwang, Young Kyu,Kwak, Jaesung. "Ag(I)-Catalyzed C-H Carboxylation of Thiophene Derivatives". . p. 3136 - 3144. Retrieved 2021/09/30.