(7-Bromo-1-benzothiophen-2-yl)methanol

Base Information

• Chemical Name: (7-Bromo-1-benzothiophen-2-yl)methanol
• CAS No.: 1171926-64-9
• Molecular Formula: C₉H₇BrOS
• Molecular Weight: 243.124
• Hs Code.: 2934208090
• DSSTox Substance ID: DTXSID601295171
• Mol file: 1171926-64-9.mol

Synonyms:(7-bromo-1-benzothiophen-2-yl)methanol;1171926-64-9;(7-Bromobenzo[b]thiophen-2-yl)methanol;Benzo[b]thiophene-2-methanol, 7-bromo-;SCHEMBL1850712;GOQLHIBVKJDKPR-UHFFFAOYSA-N;DTXSID601295171;WWB92664;7-Bromobenzo[b]thiophene-2-methanol;MFCD12032282;AKOS015835866;AT26033;CF-0742;(7-Bromo-1-benzothiophene-2-yl)methanol;(7-Bromo-benzo[b]thiophen-2-yl)-methanol;7-Bromo-2-(hydroxymethyl)benzo[b]thiophene;CS-0155817;EN300-359247

Chemical Property of (7-Bromo-1-benzothiophen-2-yl)methanol

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 241.94010
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

98%min ^*data from raw suppliers

(7-Bromo-1-benzothiophen-2-yl)methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)Br)SC(=C2)CO

Technology Process of (7-Bromo-1-benzothiophen-2-yl)methanol

There total 4 articles about (7-Bromo-1-benzothiophen-2-yl)methanol 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: 83.0%

7-bromo-1-benzothiophene-2-carboxylic acid (19075-59-3) → (7-bromo-1-benzothiophen-2-yl)methanol (1171926-64-9)

Guidance literature:

With borane-THF; at 60 ℃; for 3h; Cooling with ice;

Reference yield:

7-bromobenzo[b]thiophene-2-carbaldehyde (19075-47-9) → (7-bromo-1-benzothiophen-2-yl)methanol (1171926-64-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.5b12579

Reference yield:

1-bromo-2-(methylsulfinyl)benzene (126218-83-5,146235-11-2,7321-58-6) → (7-bromo-1-benzothiophen-2-yl)methanol (1171926-64-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 16 h / -78 - 65 °C / Inert atmosphere

2: iodine; oxygen / toluene / 16 h / 80 °C

3: sodium tetrahydroborate / ethanol / 1 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; sodium tetrahydroborate; trifluoromethylsulfonic anhydride; iodine; oxygen; In ethanol; dichloromethane; toluene;

DOI:10.1021/jacs.5b12579

upstream raw materials:

7-bromo-1-benzothiophene-2-carboxylic acid

1-bromo-2-(methylsulfinyl)benzene

7-bromobenzo[b]thiophene-2-carbaldehyde

Downstream raw materials:

N-(2-hydroxyethyl)-3-{2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl}benzamide

N-(2-amino-2-oxoethyl)-3-{2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl}benzamide

N-(2-methoxyethyl)-3-{2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl}benzamide

3-[2-(3-chloro-5-fluorobenzyl)-1-benzothiophen-7-yl]-N-(2-methoxyethyl)benzamide

Refernces

• 1、 Setoh, Masaki,Ishii, Naoki,Kono, Mitsunori,Miyanohana, Yuhei,Shiraishi, Eri,Harasawa, Toshiya,Ota, Hiroyuki,Odani, Tomoyuki,Kanzaki, Naoyuki,Aoyama, Kazunobu,Hamada, Teruki,Kori, Masakuni. "Discovery of the first potent and orally available agonist of the orphan G-protein-coupled receptor 52". . p. 5226 - 5237. Retrieved 2014/07/08.