2-Bromo-5-hexylthiophene
[CAS# 211737-28-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Thiophene compound
• Name: 2-Bromo-5-hexylthiophene
• Synonyms: 5-Bromo-2-hexylthiophene
• Molecular Formula: C₁₀H₁₅BrS
• Molecular Weight: 247.20
• CAS Registry Number: 211737-28-9
• EC Number: 624-890-0
• SMILES: CCCCCCC1=CC=C(S1)Br

Properties

• Density: 1.274±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.535, Calc.^*
• Boiling Point: 273.6±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 119.3±21.8 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06 Danger
• Hazard Statements: H301-H318-H413
• Precautionary Statements: P264-P264+P265-P270-P273-P280-P301+P316-P305+P354+P338-P317-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

2-Bromo-5-hexylthiophene is a specialized organic compound that belongs to the class of thiophene derivatives, a group of compounds with an important role in organic electronics and materials science. This chemical has the molecular formula C10H13BrS and consists of a thiophene ring substituted with a bromo group at the 2-position and a hexyl group at the 5-position. The unique combination of these substituents imparts distinct electronic and structural properties that are utilized in various fields, including organic semiconductors, organic solar cells, and electronic devices.

The discovery of 2-bromo-5-hexylthiophene is closely tied to the study of thiophene-based materials, which have been explored for their potential in electronic applications since the mid-20th century. The introduction of halogen and alkyl groups onto the thiophene ring was found to significantly influence the material's electronic properties, making it more suitable for integration into organic electronic devices. Specifically, the bromo group at the 2-position of the thiophene ring serves as a point for further functionalization or coordination with other materials, while the hexyl group at the 5-position enhances the solubility of the compound in organic solvents, facilitating its processing in device fabrication.

One of the primary applications of 2-bromo-5-hexylthiophene is in the field of organic electronics. As a building block for organic semiconductors, it is frequently used in the synthesis of conjugated polymers and small molecules that are essential in the fabrication of organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and organic solar cells (OSCs). The hexyl group improves the compound’s solubility and allows for easier processing, while the bromo group provides a site for further chemical modifications, such as the creation of copolymers with other thiophene derivatives. These copolymers often exhibit enhanced charge transport properties, making them highly suitable for use in thin-film transistors and solar cells.

In addition to its role in organic electronics, 2-bromo-5-hexylthiophene has applications in materials science for the development of novel conductive materials and sensors. Its ability to undergo cross-coupling reactions, such as the Suzuki or Stille coupling, makes it a versatile intermediate for the synthesis of more complex organic structures, often incorporated into new materials for advanced electronic applications.

In summary, 2-bromo-5-hexylthiophene is an important compound in the development of organic semiconductors and electronic devices. Its structural properties make it a valuable building block for the creation of functional materials used in the manufacture of OLEDs, OFETs, and OSCs, as well as in other cutting-edge electronic technologies.