Benzo[b]thiophene-3-butanoic acid

Base Information

• Chemical Name: Benzo[b]thiophene-3-butanoic acid
• CAS No.: 24444-97-1
• Molecular Formula: C₁₂H₁₂O₂S
• Molecular Weight: 220.292
• DSSTox Substance ID: DTXSID30500487
• Mol file: 24444-97-1.mol

Synonyms:4-Benzo[b]thiophen-3-yl-buttersaeure;4-benzo[b]thiophen-3-yl-butyric acid;Benzo[b]thiophene-3-butanoic acid;

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

Chemical Property:

• PSA: 65.54000
• LogP: 3.30860
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 220.05580079
• Heavy Atom Count: 15
• Complexity: 230

Purity/Quality:

4-(1-benzothiophen-3-yl)butanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 12 articles about Benzo[b]thiophene-3-butanoic 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: 83.0%

(E)-4-(benzo[b]thiophen-3-yl)but-3-enoic acid → 4-(benzo[b]thiophen-3-yl)butanoic acid (24444-97-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; ethyl acetate; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02851

Reference yield:

benzothiophene-3-carboxaldehyde (5381-20-4) → 4-(benzo[b]thiophen-3-yl)butanoic acid (24444-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butylate / dichloromethane / 12 h / 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 1 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; potassium tert-butylate; hydrogen; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/acs.orglett.5b02851

Reference yield:

Benzo[b]thiophene (95-15-8,11095-43-5) → 4-(benzo[b]thiophen-3-yl)butanoic acid (24444-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / SnCl₄ / benzene / 24 h / 0 - 20 °C

2: 1.) NH₂NH₂*H₂O, NaOH / 1.) diethylene glycol, reflux, 2 h, 2.) diethylene glycol, reflux, 3 h

With sodium hydroxide; tin(IV) chloride; hydrazine hydrate; In benzene;

DOI:10.1002/jhet.5570350325

upstream raw materials:

4-benzo[b]thiophen-3-yl-4-oxo-butyric acid

4-benzo[b]thiophen-3-yl-4-oxo-butyric acid methyl ester

3-(3-Chloro-propyl)-benzo[b]thiophene

Benzo[b]thiophene

Refernces

• 1、 Motiwala, Hashim F.,Vekariya, Rakesh H.,Aubé, Jeffrey. "Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol". supporting information. p. 5484 - 5487. Retrieved 2015/11/18.