3-Benzoylthiophene

Base Information

• Chemical Name: 3-Benzoylthiophene
• CAS No.: 6453-99-2
• Molecular Formula: C11H8OS
• Molecular Weight: 188.25
• Hs Code.: 2934999090
• NSC Number: 66006
• DSSTox Substance ID: DTXSID20289991
• Nikkaji Number: J81.222F
• Wikidata: Q82027554
• Mol file: 6453-99-2.mol

Synonyms:3-BENZOYLTHIOPHENE;6453-99-2;phenyl(thiophen-3-yl)methanone;phenyl(3-thienyl)methanone;METHANONE,PHENYL-3-THIENYL-;MFCD00114995;Phenyl 3-Thienyl ketone;NSC66006;Cambridge id 5103831;NCIOpen2_000319;SCHEMBL838599;Phenyl-thiophen-3-yl-methanone;DTXSID20289991;HMS1577E17;NSC 66006;NSC-66006;AKOS009505285;MB00688

Chemical Property of 3-Benzoylthiophene

Chemical Property:

• Vapor Pressure: 0.000956mmHg at 25°C
• Melting Point: 63.5°C
• Refractive Index: 1.609
• Boiling Point: 303 °C at 760 mmHg
• Flash Point: 137 °C
• PSA: 45.31000
• Density: 1.198 g/cm³
• LogP: 2.97910
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 188.02958605
• Heavy Atom Count: 13
• Complexity: 185

Purity/Quality:

99% ^*data from raw suppliers

3-Benzoylthiophene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=CSC=C2

Technology Process of 3-Benzoylthiophene

There total 78 articles about 3-Benzoylthiophene 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: 99.0%

3-benzylthiophene (27921-48-8) → 3-benzoylthiophene (6453-99-2)

Guidance literature:

With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,1,2,2-tetrachloroethane; at 130 ℃; for 10h; Autoclave;

DOI:10.1016/j.tet.2015.07.042

Reference yield: 97.0%

3-Bromothiophene (872-31-1) + phenylglyoxylic acid potassium salt (63468-90-6) → 3-benzoylthiophene (6453-99-2)

Guidance literature:

3-Bromothiophene; phenylglyoxylic acid potassium salt; With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-Phenanthroline; palladium(II) hexafluoroacetylacetonate; cyclohexylamine; copper(I) bromide; In quinoline; at 100 ℃; for 10h; Inert atmosphere; Molecular sieve;

With hydrogenchloride; In tetrahydrofuran; quinoline; water; at 80 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.201101103

Reference yield: 96.0%

phenyl(thiophen-3-yl)methyl acetate (185329-74-2) → 3-benzoylthiophene (6453-99-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; chlorobenzene; at 130 ℃; for 2h;

upstream raw materials:

3-thienyl lithium

benzonitrile

3-thiophenecarbonitrile

3-thiophene carboxylic acid chloride

Downstream raw materials:

2,4-dibenzoylthiophene

3-((4-(tert-butyl)phenyl)(phenyl)methyl)thiophene

phenyl-[3]thienyl ketone-(2,4-dinitro-phenylhydrazone)

phenyl-thiophen-3-yl-methanone semicarbazone

Refernces

• 1、 Cavallo, Luigi,Nolan, Steven P.,Poater, Albert,Szostak, Michal,Yang, Shiyi,Zhou, Tongliang. "Suzuki-Miyaura cross-coupling of esters by selective O-C(O) cleavage mediated by air- And moisture-stable [Pd(NHC)(μ-Cl)Cl]2precatalysts: Catalyst evaluation and mechanism". . p. 3189 - 3197. Retrieved 2021/05/25.
• 2、 Li, Guangchen,Ma, Siyue,Szostak, Michal,Zhou, Tongliang. "Suzuki-Miyaura Cross-Coupling of Amides using Well-Defined, Air-Stable [(PR3)2Pd(II)X2] Precatalysts". supporting information. . Retrieved 2020/05/26.