153561-74-1

Basic information

• Product Name: 2-Bromo-5-dodecylthiophene
• Synonyms: 2-Bromo-5-dodecylthiophene
• CAS NO: 153561-74-1
• Molecular Formula: C₁₆H₂₇BrS
• Molecular Weight: 331.35458
• Mol File: 153561-74-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 162°C/2mmHg(lit.)
• Flash Point: >110℃
• Appearance: /
• Density: 1.105 g/mL at 25 °C
• Refractive Index: n20/D1.510
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Bromo-5-dodecylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-dodecylthiophene(153561-74-1)
• EPA Substance Registry System: 2-Bromo-5-dodecylthiophene(153561-74-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 153561-74-1(Hazardous Substances Data)

Usage

Description

2-Bromo-5-dodecylthiophene is an organic compound that belongs to the class of thiophenes, which are heterocyclic compounds with a sulfur atom. It is characterized by the presence of a bromine atom at the 2nd position and a dodecyl group attached to the 5th position. 2-Bromo-5-dodecylthiophene is known for its unique chemical properties and potential applications in various industries.

Uses

Used in Semiconductor Industry:
2-Bromo-5-dodecylthiophene is used as a terminal building block for semiconducting polymers and oligomers. Its incorporation into these materials enhances their solubility and mobility, which are crucial factors for the performance of semiconductor devices. The increased solubility allows for better processability and film formation, while the improved mobility contributes to higher charge carrier transport efficiency in the resulting devices.
Used in Organic Electronics:
In the field of organic electronics, 2-Bromo-5-dodecylthiophene can be utilized as a key component in the design and synthesis of novel organic materials with tailored electronic properties. Its unique structure and functional groups enable the development of materials with improved charge transport characteristics, which can be applied in organic solar cells, organic light-emitting diodes (OLEDs), and organic field-effect transistors (OFETs).
Used in Chemical Synthesis:
2-Bromo-5-dodecylthiophene can also serve as a valuable intermediate in the synthesis of various organic compounds, such as pharmaceuticals, agrochemicals, and specialty chemicals. Its bromine atom and dodecyl chain provide opportunities for further functionalization and modification, allowing chemists to create a wide range of derivatives with diverse applications.

Upstream product

• 4861-61-4 2-dodecylthiophene 
• 143-15-7 1-dodecylbromide 

Downstream Products

• 1258753-94-4 C₆₂H₇₀O₈S₄ 
• 1443982-39-5 4,8-bis(4-dodecylphenyl)-2,6-bis(5-dodecylthien-2-yl)benzo[1,2-d;4,5-d′]bis(oxazole) 
• 1375353-61-9 C₃₀H₄₅O₆S^(1-)*Li⁽¹⁺⁾ 
• 1375353-56-2 sodium 2-(2-(2-(2-(4-(5-dodecylthiophen-2-yl)phenoxy)ethoxy)ethoxy)ethoxy)acetate 
• 1375353-50-6 2-(2-(2-(4-(5-dodecylthiophen-2-yl)phenoxy)ethoxy)ethoxy)ethanol 
• 1299470-13-5 C₂₂H₃₂OS 
• 1227468-69-0 2,3-bis(4-(dodecyloxy)phenyl)-7,8-bis(5-dodecylthiophen-2-yl)pyrazino[2,3-g]quinoxaline 
• 153561-79-6 5,5'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene 

Relevant articles and documents

Selective synthesis of α-substituted oligothiophenes

An improved synthesis of selectively mono- and dibrominated oligothiophenes using the system N-bromosuccinimide/dimethylformamide is reported together with the preparation of the corresponding α-alkyl and α,α-dialkyl derivatives which represent potent biologically active agents.

End-capping of conjugated thiophene-benzene aromatic systems

The synthesis of end-capped thieno[3,2-f:4,5-f′]bis[1]benzothiophene was achieved from thiophene and 2,5-thiophenedicarboxaldehyde. Specifically, hexyl and dodecyl end-capping groups conferred reversible redox behavior as evidenced by cyclic voltammetry with oxidation potentials of 0.73 V versus Fc/Fc+ couple. An extensive spectrophotometric analysis is reported.

Probe of molecular ordering in photoconductive smectic mesophases by transient photocurrent measurement

We have studied the carrier transport properties of the two series of smectic mesophases, from SmA to SmE phases, and from SmC to SmG phases in 2-pahenynaphthalene and terthiophene derivatives by time of flight measurements. We examine the experimental data with the hopping transport formalism as a function of the molecular distance with the reference to that from X-ray diffraction. We propose another aspect of the carrier transport characteristics as a probe for elucidating the molecular alignment in the smectic layer.

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.

Bent-core mesogens with thiophene units

Bent-core mesogens with thiophene and 2,2′-bithiophene units at the periphery of the aromatic core were synthesized and investigated by polarizing microscopy, XRD and electrooptical methods. Resorcinol, 2,7-naphthalenediol and 3,4′-biphenyldiol were used as bent units, phenyl thiophene-2-carboxylates form the rod-like wings and n-alkyl chains as well as olefin- and silylated-terminated alkyl chains were attached as flexible end-groups. A broad variety of different mesophase structures, incorporating ferroelectric and antiferroelectric switching smectic as well as modulated smectic phases, was obtained. Compared with the corresponding benzoates, these thiophene derived compounds form nearly identical LC phase structures, but have significantly reduced transition temperatures, which make them advantageous for applications.