4H-Cyclopenta[b]thiophen-6(5H)-one

Base Information

• Chemical Name: 4H-Cyclopenta[b]thiophen-6(5H)-one
• CAS No.: 5650-52-2
• Molecular Formula: C7H6 O S
• Molecular Weight: 138.19
• Hs Code.: 2934999090
• European Community (EC) Number: 823-210-1
• NSC Number: 241111
• DSSTox Substance ID: DTXSID50311299
• Nikkaji Number: J1.063.833J
• Wikidata: Q72464792
• Mol file: 5650-52-2.mol

Synonyms:4H-Cyclopenta[b]thiophen-6(5H)-one;5650-52-2;4,5-dihydrocyclopenta[b]thiophen-6-one;4H,5H,6H-cyclopenta[b]thiophen-6-one;6H-Cyclopenta[b]thiophen-6-one, 4,5-dihydro-;4,5-dihydro-6H-cyclopenta[b]thiophen-6-one;MFCD03426936;NSC241111;SCHEMBL350515;DTXSID50311299;AKOS006280045;CS-W003073;GS-4039;NSC 241111;NSC-241111;4,5-dihydro-cyclopenta[b]thiophen-6-one;SY027678;AMMONIUMIRON(III)SULFATEDODECAHYDRATE;AM20100391;FT-0660291;4,5-Dihydro-6H-cyclopenta[b]thiophene-6-one;EN300-136799;J-515445;Z1198162777

Chemical Property of 4H-Cyclopenta[b]thiophen-6(5H)-one

Chemical Property:

• Vapor Pressure: 0.0398mmHg at 25°C
• Melting Point: 90-91 °C
• Boiling Point: 239.6°Cat760mmHg
• Flash Point: 98.7°C
• PSA: 45.31000
• Density: 1.322g/cm³
• LogP: 1.87700
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 138.01393598
• Heavy Atom Count: 9
• Complexity: 144

Purity/Quality:

99.0%Min ^*data from raw suppliers

4H-Cyclopenta[b]thiophen-6(5H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)C2=C1C=CS2

Technology Process of 4H-Cyclopenta[b]thiophen-6(5H)-one

There total 24 articles about 4H-Cyclopenta[b]thiophen-6(5H)-one 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: 54.0%

3-(3-thienyl)propanoic acid (16378-06-6) → 4,5-dihydro-6H-cyclopenta[b]thiophen-6-one (5650-52-2)

Guidance literature:

With phosphorus pentaoxide; methanesulfonic acid; at 20 ℃; for 0.666667h;

DOI:10.1002/ejoc.200400351

Reference yield: 42.0%

1-(thiophen-3-yl)-3-(trimethylsilyl)prop-2-yn-1-ol (849769-14-8) → 4,5-dihydro-6H-cyclopenta[b]thiophen-6-one (5650-52-2)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; Tri(p-tolyl)phosphine; In toluene; for 16h; Reflux;

Reference yield: 38.0%

1-(thiophen-2-yl)-3-(trimethylsilyl)prop-2-yn-1-ol (21980-45-0) → 4,5-dihydro-6H-cyclopenta[b]thiophen-6-one (5650-52-2)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; Tri(p-tolyl)phosphine; In toluene; for 16h; Reflux;

upstream raw materials:

3-thienylpropionic acid chloride

2,3-Dibromo-4,5-dihydro-cyclopenta[b]thiophen-6-one

3-(3-thienyl)propanoic acid

1-(thiophen-2-yl)-3-(trimethylsilyl)prop-2-yn-1-ol

Downstream raw materials:

4,5-dihydro-5-methyl-6H-cyclopentathiophen-6-one

ethyl 1-(2',4'-dichlorophenyl)-1,4-dehydro-thieno[3',2':4,5]cyclopenta[1,2-c]pyrazol-3-carboxylate

Refernces

• 1、 Vekariya, Rakesh H.,Horton, Matthew C.,Aubé, Jeffrey. "Hexafluoro-2-propanol-promoted intramolecular friedel-crafts acylation". . p. 486 - 498. Retrieved 2019/08/20.
• 2、 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.