Benzo[b]thiophen-3-yl acetate

Base Information

• Chemical Name: Benzo[b]thiophen-3-yl acetate
• CAS No.: 24434-82-0
• Molecular Formula: C10H8 O2 S
• Molecular Weight: 192.238
• Hs Code.: 2934999090
• European Community (EC) Number: 246-246-4
• DSSTox Substance ID: DTXSID30179192
• Nikkaji Number: J236.696G
• Wikidata: Q83049701
• Mol file: 24434-82-0.mol

Synonyms:benzo[b]thiophen-3-yl acetate;24434-82-0;3-Acetoxythianaphthene;1-benzothiophen-3-yl acetate;Benzo(b)thiophen-3-yl acetate;EINECS 246-246-4;Benzo(b)thiophene-3-ol, acetate;Benzo[b]thiophene-3-ol, acetate;starbld0020279;1-Benzothien-3-yl acetate #;SCHEMBL2025468;IFMOFXZTHWSMEA-UHFFFAOYSA-;DTXSID30179192;AC9432;MFCD00005865;SY253153

Chemical Property of Benzo[b]thiophen-3-yl acetate

Chemical Property:

• Vapor Pressure: 0.000574mmHg at 25°C
• Boiling Point: 311.2°Cat760mmHg
• Flash Point: 142°C
• PSA: 54.54000
• Density: 1.275g/cm³
• LogP: 2.82660
• XLogP3: 2.8
• 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:

98%Min ^*data from raw suppliers

Benzo[b]thiophen-3-ylacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CSC2=CC=CC=C21

Technology Process of Benzo[b]thiophen-3-yl acetate

There total 34 articles about Benzo[b]thiophen-3-yl acetate 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: 89.0%

N,N-diethyl-2-methylsulfanylbenzamide (65935-87-7) + acetyl chloride (75-36-5) → benzo[b]thiophen-3-yl acetate (24434-82-0)

Guidance literature:

N,N-diethyl-2-methylsulfanylbenzamide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

acetyl chloride; With sodium hydride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2005.01.038

Reference yield: 89.0%

thioindoxyl (130-03-0) + acetyl chloride (75-36-5) → benzo[b]thiophen-3-yl acetate (24434-82-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 10h;

DOI:10.1016/j.tet.2005.07.050

Reference yield:

N,N-diethylbenzamide (1696-17-9) → benzo[b]thiophen-3-yl acetate (24434-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1: s-BuLi; TMEDA / tetrahydrofuran

2: LDA / tetrahydrofuran / -78 - 20 °C

3: 89 percent / NaH / tetrahydrofuran / 10 h / 20 °C

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/j.tet.2005.07.050

upstream raw materials:

3-hydroxybenzothiophene

acetyl chloride

2-methyl-1,2-benzisothiazole-3(2H)-one

potassium acetate

Downstream raw materials:

2-cyano-3-oxo-3-(1-phenyl-1H-benzothieno<3,2-c>pyrazol-3-yl)-N-phenyl-propanamide

1-phenyl-1H-benzothieno<3,2-c>pyrazole-3-carboxylic acid ethyl ester

1-phenyl-1H-benzothieno<3,2-c>pyrazole-3-carboxylic acid

1-phenyl-1H-benzothieno<3,2-c>pyrazole-3-carbonyl chloride

Refernces

• 1、 Hansen, Finn K.,Khankischpur, Mehdi,Tolaymat, Ibrahim,Mesaros, Renata,Dannhardt, Gerd,Geffken, Detlef. "Efficient synthesis and 5-LOX/COX-inhibitory activity of some 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives". . p. 5031 - 5034. Retrieved 2012/08/28.
• 2、 Pradhan, Tarun Kanti,De, Asish,Mortier, Jacques. "Application of directed metalation in synthesis. Part 8: Interesting example of chemoselectivity in the synthesis of thioaurones and hydroxy ketones and a novel anionic ortho-Fries rearrangement used as a tool in the synthesis of thienopyranones and thiafluorenones". . p. 9007 - 9017. Retrieved 2007/10/03.