148256-63-7

Basic information

• Product Name: 2,5-DIBROMO-3-DODECYLTHIOPHENE
• Synonyms: 2,5-DIBROMO-3-DODECYLTHIOPHENE;2,5-DIBROM-3-DODECYLTHIOPHEN 97%;2, ,5-Bromo-3-dodecylthiophene;2,5-DibroMo-3-n-dodecylthiophene, 97%;2,5-Dibromo-3-laurylthiophene;2,5-DibroMo-3-dodecylthiophene,97%;DibroMo-3-dodecylthioph;Thiophene,2,5-dibroMo-3-dodecyl-
• CAS NO: 148256-63-7
• Molecular Formula: C₁₆H₂₆Br₂S
• Molecular Weight: 410.25
• Product Categories: Thiophenes;Organic Electronics and Photonics;Synthetic Tools and Reagents;Thiophene Monomers and Building Blocks;Thiophene Series
• Mol File: 148256-63-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 135 °C2.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.321 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.35E-05mmHg at 25°C
• Refractive Index: n20/D 1.53(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2,5-DIBROMO-3-DODECYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIBROMO-3-DODECYLTHIOPHENE(148256-63-7)
• EPA Substance Registry System: 2,5-DIBROMO-3-DODECYLTHIOPHENE(148256-63-7)

Safety Data

• Hazard Codes: Xi:
• Statements: R36:
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 148256-63-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to yellow liquid

Uses

2,5-Dibromo-3-n-dodecylthiophene is used as an OLED intermediate, flavor and fragrance intermediate.

InChI:InChI=1/C16H27BrS/c1-2-3-4-5-6-7-8-9-10-11-12-15-13-14-18-16(15)17/h13-14H,2-12H2,1H3

Upstream product

• 104934-52-3 3-dodecylthiophene 
• 143-15-7 1-dodecylbromide 
• 15890-72-9 laurylmagnesium bromide 

Downstream Products

• 1245707-29-2 1,4-bis((E)-2-(5-bromo-3-dodecylthiophen-2-yl)vinyl)benzene 
• 1299469-86-5 C₂₃H₃₃BrOS 
• 1299469-91-2 C₃₅H₅₈OS 

Relevant articles and documents

Patchy Nanofibers from the Thin Film Self-Assembly of a Conjugated Diblock Copolymer

An unexpected morphology comprising patchy nanofibers can be accessed from the self-assembly of an all-conjugated, polyselenophene-block-polythiophene copolymer. This morphology consists of very small (10 nm), polythiophene- and polyselenophene-rich domains and is unprecedented for both conjugated polymers and diblock copolymers in general. We propose that the patchy morphology occurs from the enhanced miscibility of the blocks arising from the longer alkyl chains in comparison to similar block copolymers with shorter alkyl chains, which fully phase separate, as well as the difference in rigidity between the polythiophene and polyselenophene blocks. This work demonstrates a facile way to tune the self-assembly behavior of conjugated block copolymers by modification of the side chain substituents.

Synthesis and mesophase behavior of phenylthiophene based amphiphilic molecules

Novel amphiphilic molecules consisting of a rigid 2-phenylthiophene core, with a polar flexible tri(oxylethylene) moiety attached to the phenyl ring and one or two alkyl chains attached to the thiophene ring at the other side have been synthesized by using Ni(II) and Pd(0) catalyzed coupling reaction as key steps. The tri(oxylethylene) moieties were terminated with hydroxyl group, sodium carboxylate group and lithium carboxylate group respectively. The thermotropic and solvent induced liquid crystalline behavior of these substances was investigated by polarized optical microscopy, differential scanning calorimetry and X-ray diffraction. Thereby the influence of the terminal groups attached to the tri(oxylethylene) moities as well as the influence of the length and the number of the alkyl chains on the mesophase behavior were investigated. The single alkyl chain Na-carboxylate termianted derivatives show smectic A phases, double alkyl chain Na-carboxylate terminated derivatives show a thermo tropic hexagonal columnar mesophase, while columnar mesophases are found in both single and double alkyl chain Li-carbonate terminated derivatives. The model for molecular organization in the hexagonal columnar mesophase is established.

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.