Methyl 5-bromo-1-benzothiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 5-bromo-1-benzothiophene-2-carboxylate
• CAS No.: 7312-11-0
• Molecular Formula: C10H7BrO2S
• Molecular Weight: 271.134
• Hs Code.: 2934999090
• European Community (EC) Number: 692-361-1
• DSSTox Substance ID: DTXSID00384973
• Wikidata: Q72488403
• Mol file: 7312-11-0.mol

Synonyms:7312-11-0;methyl 5-bromo-1-benzothiophene-2-carboxylate;methyl 5-bromobenzo[b]thiophene-2-carboxylate;5-bromobenzothiophene-2-carboxylic acid methyl ester;5-Bromo-benzo[b]thiophene-2-carboxylic acid methyl ester;Methyl 5-Bromo-1-Benzothiophene-2Carboxylate;Maybridge4_002488;SCHEMBL256555;DTXSID00384973;XDYVZHUZZZKQOS-UHFFFAOYSA-N;HMS1528B02;AMY15385;FD7324;MFCD05662034;AKOS005071196;CCG-249609;PB18671;IDI1_032366;BP-20476;Methyl5-BroMobenzo[b]thiophen-2-carboxylate;CS-0053872;FT-0636430;methyl 5-bromobenzo[b]thiophen-2-carboxylate;methyl 5-bromo-benzo[b]thiophene-2-carboxylate;5-BROMO-BENZOTHIOPHENE-2-CARBOXYLIC ACID;EN300-7422931;7X-0709;5-Bromo-benzo[b]thiophene-2-carboxylic methyl ester;J-522464;5-Bromobenzo[b]thiophene-2-carboxylic acid methyl ester;Z1269233055

Chemical Property of Methyl 5-bromo-1-benzothiophene-2-carboxylate

Chemical Property:

• Vapor Pressure: 2.47E-05mmHg at 25°C
• Melting Point: 110 °C
• Refractive Index: 1.663
• Boiling Point: 358.9 °C at 760 mmHg
• Flash Point: 170.8 °C
• PSA: 54.54000
• Density: 1.622 g/cm³
• LogP: 3.45040
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 269.93501
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

97% ^*data from raw suppliers

5-Bromobenzothiophene-2-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(S1)C=CC(=C2)Br
• Uses: 5-Bromobenzothiophene-2-carboxylic acid methyl ester is used in the preparation of new derivatives of (heterocycle-tetrahydropyridine)-(piperazinyl)-1-alkanone and (heterocycle-dihydropyrrolidine)-(piperazinyl)-1-alkanone, as p75 neurotrophin receptor ligands for treating neurological and neurodegenerative diseases.

Technology Process of Methyl 5-bromo-1-benzothiophene-2-carboxylate

There total 3 articles about Methyl 5-bromo-1-benzothiophene-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: 99.0%

5-bromobenzo[b]thiophene (4923-87-9) + carbon dioxide (124-38-9,18923-20-1) + methyl iodide (74-88-4) → 5-bromo-1-benzothiophene-2-carboxylic acid methyl ester (7312-11-0)

Guidance literature:

5-bromobenzo[b]thiophene; carbon dioxide; With 18-crown-6 ether; cesium fluoride; lithium tert-butoxide; at 160 ℃; for 3h; under 760.051 Torr; Inert atmosphere; Sealed tube;

methyl iodide; at 60 ℃; for 2h;

DOI:10.1002/chem.201805926

Reference yield: 92.0%

Methyl thioglycolate (2365-48-2) + 5-bromo-2-fluorobenzaldehyde (93777-26-5) → 5-bromo-1-benzothiophene-2-carboxylic acid methyl ester (7312-11-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 15h;

DOI:10.1016/j.ejmech.2019.04.024

Reference yield: 87.0%

→ 5-bromo-1-benzothiophene-2-carboxylic acid methyl ester (7312-11-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 3h;

upstream raw materials:

Methyl thioglycolate

5-bromo-2-fluorobenzaldehyde

5-bromobenzo[b]thiophene

carbon dioxide

Downstream raw materials:

methyl 5-iodobenzo[b]thiophene-2-carboxylate

methyl 5-(4-methoxyphenyl)benzo[b]thiophene-2-carboxylate

5-phenylbenzo[b]thiophene-2-carboxylic acid

3-fluoro-5-phenyl-benzo[b]thiophene-2-carboxylic acid