16303-58-5

Basic information

• Product Name: 5,5'-DIMETHYL-2,2'-BITHIOPHENYL
• Synonyms: 5,5'-Dimethyl-2,2'-bithiophene;5,5'-DIMETHYL-2,2'-BITHIOPHENYL;5,5'-dimethyl-2,2'-bithiopheny;5,5'-Dimethyl-2,2'-bithiophene,99%;2-methyl-5-(5-methylthiophen-2-yl)thiophene
• CAS NO: 16303-58-5
• Molecular Formula: C₁₀H₁₀S₂
• Molecular Weight: 194.32
• Mol File: 16303-58-5.mol
• Article Data: 32

Chemical Properties

• Melting Point: 65-68 °C
• Boiling Point: 262.9 °C at 760 mmHg
• Flash Point: 81.8 °C
• Appearance: Yellow to light brown/Crystals
• Density: 1.169 g/cm³
• Storage Temp.: Refrigerator (+4°C)
• CAS DataBase Reference: 5,5'-DIMETHYL-2,2'-BITHIOPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5'-DIMETHYL-2,2'-BITHIOPHENYL(16303-58-5)
• EPA Substance Registry System: 5,5'-DIMETHYL-2,2'-BITHIOPHENYL(16303-58-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 16303-58-5(Hazardous Substances Data)

Usage

Chemical Properties

yellow to light brown crystals

Upstream product

• 16494-36-3 2-iodo-5-methylthiophene 
• 32358-94-4 5-methyl-2,2'-bithiophene-5'-carboxaldehyde 
• 765-58-2 2-bromo-5-methyl thiophene 
• 133118-10-2 5-methyl-2-thienylmagnesium iodide 
• 492-97-7 2,2'-Bithiophene 
• 74-88-4 methyl iodide 
• 63762-42-5 2-lithio-5-methylthiophene 
• 71486-35-6 5-(2'-thienyl)-2-thienyllithium 
• 554-14-3 2-Methylthiophene 
• 18494-74-1 2-methyl-2,5'-bithiophene 
• 3779-27-9 2,2'-bithiophene-5-carboxaldehyde 
• 96-43-5 2-thienyl chloride 
• 273-53-0 benzoxazole 
• 17626-75-4 2-(n-propyl)-thiazole 

Relevant articles and documents

Efficient Homocoupling of Aryl- and Alkenylboronic Acids in the Presence of Low Loadings of [{Pd(μ-OH)Cl(IPr)} 2 ]

NHC-palladium(II) complex [{Pd(μ-OH)Cl(IPr)} 2 ] (IPr = bis(2,6-diisopropylphenyl)imidazolin-2-ylidene) catalyzes the oxidative coupling of a broad spectrum of aryl- and alkenylboronic acids at loadings down to 5 ppm. At the concentration of 0.05 mol% the catalyst permits an efficient reaction under base-free conditions.

Conducting Polymers from Dimethyl-2,2'-bithiophenes

Electrochemical oxidation of symmetrical dimethylbithiophenes with free α-positions yields electroactive polymers with excellent cycling ability.

Expanding tetra[2,3-thienylene]-based molecular muscles to larger [4n]annulenes

The synthesis, X-ray structure, and predicted redox-induced conformational dynamics of a thiophene-fused [12]annulene is reported. Regiospecific halogenation of the thiophene ring system and transition-metal catalyzed cross-couplings are key elements in the synthetic strategy. It is predicted (B3LYP/6-31G*) that redox-induced conformational changes yield significant dimensional changes in this annulene, thus establishing it as a candidate for single molecule actuation.

Studies on the Electronic Absorption Spectra of 2,2'-Bithienyl and Some of Its Derivatives. A Molecular Orbital Treatment

The electronic absorption spectra of 2,2'-bithienyl and a number of its derivatives have been investigated.The predominant conformer as well as the polarity of the molecule were predicted from the spectrum.Molecular orbital calculations were performed on different conformers of 5-formyl-2,2'-bithienyl and the s-trans geometry proved to be the predominant conformer of the molecule.A good agreement is observed between calculated and observed transition energy and intensity.

Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation

A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain via the Ullmann or the Suzuki coupling protocols. Finally, we have shown a one-pot sequence describing C-H borylation/Cu-catalyzed homocoupling/Pd-catalyzed Suzuki coupling to obtain π-extended arene frameworks.