24287-92-1

Basic information

• Product Name: 2-BROMO-3-IODOTHIOPHENE
• Synonyms: 2-BROMO-3-IODOTHIOPHENE
• CAS NO: 24287-92-1
• Molecular Formula: C₄H₂BrIS
• Molecular Weight: 288.93
• Mol File: 24287-92-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 252.0±20.0 °C(Predicted)
• Appearance: /
• Density: 2.465±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-BROMO-3-IODOTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-3-IODOTHIOPHENE(24287-92-1)
• EPA Substance Registry System: 2-BROMO-3-IODOTHIOPHENE(24287-92-1)

Safety Data

• Hazardous Substances Data: 24287-92-1(Hazardous Substances Data)

Usage

General Description

2-Bromo-3-iodothiophene is a chemical compound with the molecular formula C4H2BrIS. It is a heterocyclic organic compound that consists of a thiophene ring with both bromine and iodine atoms attached at the 2 and 3 positions, respectively. 2-BROMO-3-IODOTHIOPHENE is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and organic electronic materials. It is also known for its use in the field of organic chemistry as a versatile reagent for the construction of more complex compounds. Additionally, 2-Bromo-3-iodothiophene is also used in the field of materials science for the development of novel polymers and materials with unique properties.

Upstream product

• 10486-61-0 3-thienyl iodide 

Downstream Products

• 1860-99-7 2-bromothiophene-3-carbaldehyde 
• 62224-14-0 ethyl ester of 3-bromo-2-thiophenecarboxylic acid 
• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 
• 930-97-2 3-iodothiophene-2-carboxaldehyde 
• 1553280-33-3 2-bromo-3-(4-hexylphenyl)ethynylthiophene 
• 1123215-50-8 2-bromo-3-phenylethynylthiophene 
• 36155-75-6 3-acetyl-2-thienylboronic acid 
• 42877-08-7 1-(3-bromothiophen-2-yl)ethanone 
• 137272-68-5 1-(2-bromothiophen-3-yl)ethane-1-one 
• 1003-09-4 2-bromothiophene 
• 52770-39-5 2-d₁-3-bromothiophene 
• 56182-43-5 2-bromothiophene-3-carbonitrile 
• 18791-98-5 3-bromo-thiophene-2-carbonitrile 
• 463336-26-7 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbonitrile 

Relevant articles and documents

Tetrathiahexacene as building block for solution-processable semiconducting polymers: Exploring the monomer size limit

A larger fused monomer in a polythiophene chain which can improve stability and device performance has been reported. The largest building block in a soluble polythiophene so far is tetrathienoacene (P3). This polymer is very stable toward oxidation in an organic field-effect transistor and also shows high charge-carrier mobilities. The polymerization using dibromodithiophene as comonomer was performed using Pd(PPh3)4 as catalyst in toluene. The reaction mixture was heated for 40 minutes in the microwave to 150 °C with a power density of 70 W/mL. In a field-effect transistor, a good device characteristic, which is low contact resistance and low hysteresis, have been measured. The field-effect mobility does not yet reach values needed for applications but is likely to be achieved after more processing optimizations.

Tuning the antiaromatic character and charge transport of pentalene-based antiaromatic compounds by substitution

Understanding the structure-property relationships in antiaromatic molecules is crucial for controlling their electronic properties and designing new organic optoelectronic materials. Here we report the design, synthesis, and characterization of three new antiaromatic molecules (Pn, n = 1-4) based on the pentalene (P) antiaromatic core, to investigate how electron-donating and electron-accepting substituents affect P1-P4 properties. As expected, the optical, HOMO and LUMO energy levels and electronic structure are greatly modulated by core substitution. Compared to the unsubstituted compound (P1), P3 and P4 containing strong electron-withdrawing units reduced antiaromaticity as assessed by nucleus-independent chemical shift (NICS) calculations compared with P2, which is functionalized with strong electron-donating units, showing that substitution strongly tunes local antiaromaticity. Organic field-effect transistors (OFETs) fabricated using these materials indicate that P2 has an average hole mobility of ～10-4 cm2 V-1 s-1 while P3 has an average electron mobility of up to 0.03 cm2 V-1 s-1, versus FET-inactive P1. Therefore, introduction of strong π-extended electron-withdrawing or electron-donating substituents onto an antiaromatic core is an effective strategy to switch-on charge transport capacity. This journal is

ORGANIC SEMICONDUCTING COMPOUNDS AND RELATED OPTOELECTRONIC DEVICES

The present teachings relate to new organic semiconducting compounds and their use as active materials in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The present compounds can provide improved device performance, for example, as measured by power conversion efficiency, fill factor, open circuit voltage, field-effect mobility, on/off current ratios, and/or air stability when used in photovoltaic cells or transistors. The present compounds can have good solubility in common solvents enabling device fabrication via solution processes.