1-(5-BROMO-1-BENZOTHIEN-3-YL)ETHANONE

Base Information

• Chemical Name: 1-(5-BROMO-1-BENZOTHIEN-3-YL)ETHANONE
• CAS No.: 1423-63-8
• Molecular Formula: C₁₀H₇BrOS
• Molecular Weight: 255.135
• Hs Code.: 29349990
• Mol file: 1423-63-8.mol

Synonyms:Ketone,5-bromobenzo[b]thien-3-yl methyl (7CI,8CI);3-Acetyl-5-bromobenzo[b]thiophene;

Chemical Property of 1-(5-BROMO-1-BENZOTHIEN-3-YL)ETHANONE

Chemical Property:

• Vapor Pressure: 2.34E-05mmHg at 25°C
• Melting Point: 112-113 °C
• Refractive Index: 1.672
• Boiling Point: 359.7 °C at 760 mmHg
• Flash Point: 171.3 °C
• PSA: 45.31000
• Density: 1.587 g/cm³
• LogP: 3.86640

Purity/Quality:

99%min ^*data from raw suppliers

3-Acetyl-5-bromobenzo[b]thiophene ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 24/25-36/37

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(5-BROMO-1-BENZOTHIEN-3-YL)ETHANONE

There total 5 articles about 1-(5-BROMO-1-BENZOTHIEN-3-YL)ETHANONE 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: 96.0%

5-bromobenzo[b]thiophene (4923-87-9) + acetic anhydride (108-24-7) → 1-(5-bromobenzo[b]thiophen-3-yl)ethan-1-one (1423-63-8)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2018.01.026

Reference yield: 92.2%

5-bromobenzo[b]thiophene (4923-87-9) + acetyl chloride (75-36-5) → 1-(5-bromobenzo[b]thiophen-3-yl)ethan-1-one (1423-63-8)

Guidance literature:

acetyl chloride; With aluminum (III) chloride; In dichloromethane; at 0 ℃; for 0.5h;

5-bromobenzo[b]thiophene; In dichloromethane; at 25 ℃; for 2.5h;

Reference yield:

1-bromo-4-[2,2-(dimethoxy)ethylsulfanyl]benzene (118780-12-4) → 1-(5-bromobenzo[b]thiophen-3-yl)ethan-1-one (1423-63-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 42.35 g / PPA / chlorobenzene / 15 h / Heating

2: 90 percent / SnCl₄ / 1,2-dichloro-ethane / 20 h / 0 - 20 °C

With tin(IV) chloride; In 1,2-dichloro-ethane; chlorobenzene; 2: Friedel-Crafts acylation;

DOI:10.1021/jm0205189

upstream raw materials:

5-bromobenzo[b]thiophene

acetyl chloride

1-bromo-4-[2,2-(dimethoxy)ethylsulfanyl]benzene

para-bromobenzenethiol

Downstream raw materials:

5-bromobenzo[b]thiophene-3-carboxylic acid

5-hydroxybenzo[b]thiophene-3-carboxylic acid

5-methoxy-3-benzo[b]thiophenecarboxylic acid

Refernces

• 1、 Liu, Guangchang,Xu, Bo. "Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream". supporting information. p. 869 - 872. Retrieved 2018/02/09.
• 2、 Mitsumori, Susumu,Tsuri, Tatsuo,Honma, Tsunetoshi,Hiramatsu, Yoshiharu,Okada, Toshihiko,Hashizume, Hiroshi,Inagaki, Masanao,Arimura, Akinori,Yasui, Kiyoshi,Asanuma, Fujio,Kishino, Junji,Ohtani, Mitsuaki. "Synthesis and biological activity of various derivatives of a novel class of potent, selective, and orally active prostaglandin D2 receptor antagonists. 2. 6,6-dimethylbicyclo[3.1.1]heptane derivatives". . p. 2446 - 2455. Retrieved 2007/10/03.