13196-30-0

Basic information

• Product Name: 5-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one
• CAS NO: 13196-30-0
• Molecular Formula: C₈H₈OS
• Molecular Weight: 152.2135
• Mol File: 13196-30-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 242.8°C at 760 mmHg
• Flash Point: 100.6°C
• Density: 1.222g/cm³
• Vapor Pressure: 0.0333mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: 5-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one(13196-30-0)
• EPA Substance Registry System: 5-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one(13196-30-0)

Safety Data

• Hazardous Substances Data: 13196-30-0(Hazardous Substances Data)

Upstream product

• 2522-99-8 N,N-dimethyl-N-<2-methyl-3-oxo-3-(2-thienyl)propyl>ammonium chloride 
• 13679-75-9 1-thiophen-2-yl-propan-1-one 
• 1195-52-4 3-(3-thienyl)-2-propenoic acid 
• 16378-06-6 3-(3-thienyl)propanoic acid 
• 188290-36-0 thiophene 
• 79-41-4 poly(methacrylic acid) 
• 5650-52-2 4,5-dihydro-6H-cyclopenta[b]thiophen-6-one 
• 74-88-4 methyl iodide 
• 13191-26-9 2-methyl-1-(thiophen-2-yl)prop-2-en-1-one 

Downstream Products

• 827609-20-1 (R)-5-hydroxy-5-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one O-methyloxime 
• 827609-28-9 (R,R)-N-(5-hydroxy-5-methyl-5,6-dihydro-4H-cyclopenta[b]thien-6-yl)benzamide 
• 1026640-09-4 (5R,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate 
• 690656-72-5 (6S)-(-)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide 
• 690656-71-4 (6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide 
• 690656-67-8 (S)-(-)-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid 
• 690656-65-6 (R)-(+)-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid 
• 690656-63-4 5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophen-6-carboxylic acid 

Relevant articles and documents

Bridged Dithienylethylenes as Precursors of Small Bandgap Electrogenerated Conjugated Polymers

Bridged dithienylethylenes (DTEs) bearing solubilizing alkyl chains at various positions (2-5) have been synthesized by McMurry dimerization of cyclopenta[b]thiophen-6-ones. In order to introduce alkyl substituents at different positions of the DTE molecule, the precursor ketones have been prepared by different strategies based on a combination of Mannich or Wittig - Horner reaction and Friedel - Craft intramolecular cyclization. The position and the length of the alkyl substituents exert a strong effect on the ability of the precursor to undergo electrochemical polymerization. Thus, whereas substitution at the α-position of the ethylene linkage (3) results in a rapid inhibition of electropolymerization, introduction of alkyl chains at the β-position (4, 5) greatly improves the efficiency of the polymerization process. The analysis of the electrochemical and optical properties of the polymers shows that rigidification of the DTE molecule leads to a significant decrease of the oxidation potential and bandgap. A comparative analysis of DTE and its bridged analogues by means of X-ray diffraction reveals, in agreement with experimental and theoretical results, that the observed reduction of both the HOMO - LUMO gap of the precursor and the bandgap of the corresponding polymers are related to a relaxation of bond length alternation in the DTE moiety.

Diastereoselective synthesis of thieno[3′,2′:4,5]cyclopenta[1, 2-d][1,3]-oxazolines - New ligands for the copper-catalyzed asymmetric conjugate addition of diethylzinc to enones

Several new ligands featuring a rigid three ring skeleton have been prepared for the first time following a modular approach. Chirality has been introduced by use of an oxazoline moiety fused with a cyclopenta[b]thiophene backbone. The efficiency and stereochemical impact of these ligands on the copper-catalyzed enantioselective addition of Et2Zn to chalcone was examined and enantiomeric excesses up to 79% were achieved using the ligand (R,R)-16 substituted with a methyl group at the cyclopenta moiety. Computational and ESI-mass spectral studies show that these new compounds behave as monodentate ligands towards Cu+. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.