158956-23-1

Basic information

• Product Name: 2,5-DIBROMO-3-DECYLTHIOPHENE
• Synonyms: 2,5-DIBROMO-3-DECYLTHIOPHENE;2,5-DibroMo-3-n-decylthiophene, 97%
• CAS NO: 158956-23-1
• Molecular Formula: C14H22Br2S
• Molecular Weight: 382.2
• Product Categories: Organic Electronics and Photonics;Synthetic Tools and Reagents;Thiophene Monomers and Building Blocks;Thiophenes;Thiophene Series
• Mol File: 158956-23-1.mol

Chemical Properties

• Boiling Point: 168-170 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 1.372 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.38E-05mmHg at 25°C
• Refractive Index: n20/D 1.538(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,5-DIBROMO-3-DECYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIBROMO-3-DECYLTHIOPHENE(158956-23-1)
• EPA Substance Registry System: 2,5-DIBROMO-3-DECYLTHIOPHENE(158956-23-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 158956-23-1(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow liquid

Uses

Conducting polymer precursor.

InChI:InChI=1/C14H22Br2S/c1-2-3-4-5-6-7-8-9-10-12-11-13(15)17-14(12)16/h11H,2-10H2,1H3

Upstream product

• 65016-55-9 3-decylthiophene 

Relevant articles and documents

Cis/Cis-2,5-dipropenylthiophene monomers for high-molecular-weight poly(2,5-thienylene vinylene)s through acyclic diene metathesis polymerization

The synthesis of the 2,5-dipropenylthiophene monomer possessing exclusively cis-double bond configurations through the reduction of a dipropynylthiophene precursor is reported. Lindlar's catalyst is found to be completely ineffective, while a dissolving metal method involving activated zinc is successful in alkyne reduction to cis-alkenes with high yields and excellent selectivity. The acyclic diene metathesis polymerization of the monomer affords the poly(2,5-thienylene vinylene) polymer of a high molecular weight. Copyright

Regiocontrolled synthesis of poly(3-alkylthiophenes) mediated by Rieke zinc: Their characterization and solid-state properties

A systematically regiocontrolled synthesis of poly(3-alkylthiophenes) (P3AT) mediated by Rieke zinc is reported. Rieke zinc undergoes oxidative addition to 2,5-dibromo-3-alkylthiophene or 2-bromo-5-iodo-3-alkylthiophene regioselectively to afford 2-bromo-5-(bromozincio)-3-alkylthiophene (2) or 2-bromo-5-(iodozincio)-3-alkylthiophene (10). The intermediate 2 or 10 can be polymerized catalytically to a series of regiospecific poly(3-alkylthiophenes) using different catalysts. The regioregularity of the polymer chain is solely controlled by the structure of the catalyst. An almost completely regioregular head-to-tail (HT) P3AT (4) is obtained by using Ni(DPPE)Cl2 ([1,2-bis-(diphenylphosphino)ethane]nickel(II) chloride). Use of Pd(DPPE)Cl2 leads to a reduction in the regioregularity (70: 30 HT/HH), while using Ni(PPh3)4 also leads to a much reduced regioregular P3AT (63:35 HT/HH). A totally regiorandom (50:50 HT/HH) P3AT (5) is afforded by using Pd(PPh3)4. The poly(3-butylthiophene) 4a is a 97% HT regioregular polymer. Other poly(3-alkylthiophenes) (alkyl = hexyl (4b), octyl (4c), decyl (4d), dodecyl (4e), and tetradecyl (4f)) are regioregular P3ATs with the HT linkage larger than 98.5% based on NMR analysis. Electronic absorption, X-ray diffraction, and crossed polarizing micrograph studies show that the cast films of the regioregular P3ATs (4) are self-organized, crystalline, flexible, and bronze-colored films with a metallic luster, while that of the regiorandom P3ATs (5) are amorphous and orange-colored films. The regioregular P3ATs exhibit a small bandgap (1.7 eV) which is 0.4 eV lower than that of regiorandom P3ATs (2.1 eV). Regioregular HT P3ATs have considerably improved electroconductivity and other physical properties over regiorandom P3ATs.