2-Acetyl-3-bromothiophene

Base Information

• Chemical Name: 2-Acetyl-3-bromothiophene
• CAS No.: 42877-08-7
• Molecular Formula: C6H5BrOS
• Molecular Weight: 205.075
• Hs Code.: 29349990
• European Community (EC) Number: 629-028-7
• DSSTox Substance ID: DTXSID20377468
• Nikkaji Number: J1.093.418D
• Wikidata: Q72434923
• Mol file: 42877-08-7.mol

Synonyms:2-Acetyl-3-bromothiophene;42877-08-7;1-(3-bromothiophen-2-yl)ethanone;2-Acetyl-3-boromothiophene;1-(3-BROMO-2-THIENYL)-1-ETHANONE;1-(3-BROMOTHIOPHEN-2-YL)ETHAN-1-ONE;MFCD00794287;Ethanone, 1-(3-bromo-2-thienyl)-;SCHEMBL507698;DTXSID20377468;ZUXPELAHJQSZTE-UHFFFAOYSA-N;2-Acetyl-3-bromothiophene, 97%;1-(3-bromo-2-thiophenyl)ethanone;1-(3-bromanylthiophen-2-yl)ethanone;1-(3-bromo-thiophen-2-yl)-ethanone;AKOS005071342;AB07140;SY062236;FT-0658159;EN300-36968;9J-900;A826046;J-503113;Z381006388

Chemical Property of 2-Acetyl-3-bromothiophene

Chemical Property:

• Vapor Pressure: 0.00314mmHg at 25°C
• Melting Point: 38-41 °C
• Refractive Index: 1.6108
• Boiling Point: 283.537 °C at 760 mmHg
• Flash Point: 125.279 °C
• PSA: 45.31000
• Density: 1.619 g/cm³
• LogP: 2.71320
• Storage Temp.: 2-8°C(protect from light)
• Sensitive.: Stench
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 203.92445
• Heavy Atom Count: 9
• Complexity: 126

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Acetyl-3-bromothiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi, Xn
• Hazard Codes: T,Xi,Xn
• Statements: 22-36-43
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C=CS1)Br

Technology Process of 2-Acetyl-3-bromothiophene

There total 8 articles about 2-Acetyl-3-bromothiophene 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: 98.0%

3-Bromothiophene (872-31-1) + acetyl chloride (75-36-5) → 1-(3-bromothiophen-2-yl)ethanone (42877-08-7)

Guidance literature:

acetyl chloride; With aluminium trichloride; In dichloromethane; cooling;

3-Bromothiophene; In dichloromethane; at 0 - 20 ℃; for 1.66667h;

DOI:10.1021/jo051826s

Reference yield:

3-bromo-2-thiophenecarboxaldehyde (930-96-1) → 1-(3-bromothiophen-2-yl)ethanone (42877-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: magnesium; iodine / diethyl ether / 3 h / -10 - 0 °C

2: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C

With iodine; silica gel; magnesium; pyridinium chlorochromate; In diethyl ether; dichloromethane;

DOI:10.1021/acs.orglett.1c00493

Reference yield:

2-Bromo-3-iodothiophene (24287-92-1) + acetic anhydride (108-24-7) → 1-(3-bromothiophen-2-yl)ethanone (42877-08-7) + 1-(2-bromothiophen-3-yl)ethane-1-one (137272-68-5)

Guidance literature:

2-Bromo-3-iodothiophene; With ethylmagnesium chloride; In tetrahydrofuran; at 15 ℃; for 0.25h;

acetic anhydride; In tetrahydrofuran; at 20 - 25 ℃; for 0.75h; Title compound not separated from byproducts;

DOI:10.1021/jo034919n

upstream raw materials:

3-Bromothiophene

acetyl chloride

acetic anhydride

2-Bromo-3-iodothiophene

Downstream raw materials:

bromomethyl 3-bromo-2-thienyl ketone

6-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

methyl 3-phenylthiophene-2-carboxylate

1-(3-Z-phenyl-5-(p-tolyl)thiophene-2-yl)ethanone

Refernces

• 1、 Pelly, Stephen C.,Parkinson, Christopher J.,Van Otterlo, Willem A. L.,De Koning, Charles B.. "Metathesis reactions for the synthesis of ring-fused carbazoles". . p. 10474 - 10481. Retrieved 2005.
• 2、 Sun, Xiangyu,Gong, Ming,Huang, Mengmeng,Li, Yabo,Kim, Jung Keun,Kovalev, Vladimir,Shokova, Elvira,Wu, Yangjie. ""one-Pot" Synthesis of γ-Pyrones from Aromatic Ketones/Heteroarenes and Carboxylic Acids". . p. 15051 - 15061. Retrieved 2020/12/02.
• 3、 Ji, Shaomin,Ge, Jie,Escudero, Daniel,Wang, Zhijia,Zhao, Jianzhang,Jacquemin, Denis. "Molecular structure-intersystem crossing relationship of heavy-atom-free bodipy triplet photosensitizers". . p. 5958 - 5963. Retrieved 2015/06/16.