2-Acetylbenzothiophene

Base Information

• Chemical Name: 2-Acetylbenzothiophene
• CAS No.: 22720-75-8
• Molecular Formula: C10H8OS
• Molecular Weight: 176.239
• Hs Code.: 29349990
• European Community (EC) Number: 245-177-7
• UNII: ZC5EPE32DF
• DSSTox Substance ID: DTXSID3057692
• Nikkaji Number: J286.284K
• Wikidata: Q72434824
• ChEMBL ID: CHEMBL541695
• Mol file: 22720-75-8.mol

Synonyms:2-ABT cpd;2-acetylbenzothiophene

Chemical Property of 2-Acetylbenzothiophene

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00087mmHg at 25°C
• Melting Point: 86-88 ºC
• Refractive Index: 1.646
• Boiling Point: 304.5 ºC at 760 mmHg
• Flash Point: 138 ºC
• PSA: 45.31000
• Density: 1.219 g/cm³
• LogP: 3.10390
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 176.02958605
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

98%min ^*data from raw suppliers

2-Acetylbenzothiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-22
• Safety Statements: 36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC2=CC=CC=C2S1
• Uses: A novel anti-osteoporosis agent, by enhansing expression of the BMP-2 gene.

Technology Process of 2-Acetylbenzothiophene

There total 35 articles about 2-Acetylbenzothiophene 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: 100.0%

2-(ethylsulfanyl)benzenecarbaldehyde (53606-33-0) + chloroacetone (78-95-5) → 2-acetyl benzo[b]thiophene (22720-75-8)

Guidance literature:

With calcium oxide; In acetone; at 59 ℃;

DOI:10.1016/j.bmcl.2014.03.024

Reference yield: 98.0%

1-(benzo[b]thiophen-2-yl)ethanol (51868-95-2) → 2-acetyl benzo[b]thiophene (22720-75-8)

Guidance literature:

With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); potassium tert-butylate; acetone; In n-heptane; at 50 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1002/cssc.201900308

Reference yield: 95.0%

diethylacetamide (685-91-6) + sodium trisulfide (37488-76-9) + chloroacetone (78-95-5) → 2-acetyl benzo[b]thiophene (22720-75-8)

Guidance literature:

In diethyl ether; water;

upstream raw materials:

benzothiophen-2-yllithium

acetic anhydride

Benzo[b]thiophene

2-(hydroxymethyl)thiophenoxyacetone

Downstream raw materials:

1-(N-hydroxyamino)-1-(benzothien-2-yl)ethane

1-benzo[b]thiophen-2-yl-2-phenylsulfanyl-ethanone

1-benzo[b]thiophen-2-yl-2-phenylsulfanyl-ethanone-(2,4-dinitro-phenylhydrazone)

2-[1-(hydroxyimino)ethyl]-benzo[b]thiophene

Refernces

• 1、 Basha,Brooks. "Synthesis of the 5-lipoxygenase inhibitor zileuton from thiophenol". . p. 1293 - 1294. Retrieved 1993.
• 2、 Forsyth,D.A.,Olah,G.A.. "-". . p. 5309. Retrieved 1979.
• 3、 Wang, Hua,Liu, Jie,Qu, Jian-Ping,Kang, Yan-Biao. "Overcoming Electron-Withdrawing and Product-Inhibition Effects by Organocatalytic Aerobic Oxidation of Alkylpyridines and Related Alkylheteroarenes to Ketones". . p. 3942 - 3948. Retrieved 2020/03/23.
• 4、 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.