1753-75-9

Basic information

• Product Name: 5-BROMO-2,1,3-BENZOTHIADIAZOLE
• Synonyms: 5-BROMO-2,1,3-BENZOTHIADIAZOLE;5-BROMO-BENZO[1,2,5]THIADIAZOLE;BUTTPARK 95\50-70;5-Bromo-benzo[2,1,3]thiadiazole;5-Bromobenzo[c][1,2,5]thiadiazole
• CAS NO: 1753-75-9
• Molecular Formula: C₆H₃BrN₂S
• Molecular Weight: 215.07
• Product Categories: Heterocycles series
• Mol File: 1753-75-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 51-53°C
• Boiling Point: 272.2°Cat760mmHg
• Flash Point: 118.4°C
• Appearance: /
• Density: 1.859g/cm³
• Vapor Pressure: 0.0103mmHg at 25°C
• Refractive Index: 1.733
• Storage Temp.: 2-8°C
• PKA: -0.73±0.36(Predicted)
• CAS DataBase Reference: 5-BROMO-2,1,3-BENZOTHIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2,1,3-BENZOTHIADIAZOLE(1753-75-9)
• EPA Substance Registry System: 5-BROMO-2,1,3-BENZOTHIADIAZOLE(1753-75-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1753-75-9(Hazardous Substances Data)

Usage

General Description

5-Bromo-2,1,3-benzothiadiazole (also known as BBT) is a chemical compound generally used in organic semiconductors. Its molecular formula is C6H3BrN2S, and it appears as a white to beige crystalline powder. BBT is known for its high thermal stability and capacity to enhance the performance of organic field-effect transistors. The bromine atom in this compound also provides an easy pathway for various organic transformations, making it useful in synthetic chemistry and the production of polymers. It is often used in research and development settings due to its various unique properties.

InChI:InChI=1/C6H3BrN2S/c7-4-1-2-5-6(3-4)9-10-8-5/h1-3H

Upstream product

• 1575-37-7 4-Bromo-benzene-1,2-diamine 

Downstream Products

• 72023-79-1 5-bromo-4-nitro-benzo[1,2,5]thiadiazole 
• 1404481-85-1 4,5-bis[5-(4-methoxyphenyl)-2-methylthiophen-3-yl]benzo[c][1,2,5]thiadiazole 
• 1168135-03-2 5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzo[c][1,2,5]thiodiazole 
• 768-10-5 benzo[1,2,5]thiadiazol-5-ol 
• 1541809-17-9 11-(4-diphenylaminophenyl)dipyrido[3,2-a:2′,3′-c]phenazine 
• 32863-29-9 4-Nitro-5-hydroxybenz-2,1,3-thiadiazol 
• 49716-23-6 benzo[1,2,5]thiadiazole-5-carboxylic acid ethyl ester 

Relevant articles and documents

Bisthienylethenes containing a benzothiadiazole unit as a bridge: Photochromic performance dependence on substitution position

A conveniently synthesized photochromic compound, BTB-1, containing an unprecedented six-mem- bered 2, 1, 3-benzothiadiazole unit as the center ethene bridge, possesses good photochromic performance, with a high cyclization quantum yield and moderate fatigue resistance in solution or an organogel system. The fluorescence of BTB-1 can be modulated by solvato- and photochromism. However, the analogue BTB-2, in which the di- methylthiophene substituents are relocated to the 5, 6-positions of benzothia- diazole, does not show any detectable photochromism. To the best of our knowledge, this is the first example of six-membered bridge bisthienylethenes (BTEs) in which the photochromism can be controlled by the substitution position. The photochromism difference is elucidated by the analysis of resonance structure, the Woodward- Hoffmann rule, and theoretical calculations on the ground-state potential- energy surface. In a well-ordered single-crystal state, BTB-1 adopts a relatively rare parallel conformation, and forms an interesting two-dimensional structure due to the presence of multiple directional intermolecular interactions, including C-H-N and C-H-S hydrogen-bonding interactions, and π stacking interactions. This work contributes to several aspects for developing novel photochromic BTE systems with fluorescence modulation and performances controlled by substitution position in different states (solution, or- ganogel, and single crystal).

Funnel shaped molecules containing benzo/pyrido[1,2,5]thiadiazole functionalities as peripheral acceptors for organic photovoltaic applications

A series of four novel funnel shaped triphenylamine core derivatized materials with various combinations of 3,6-di-tert-butyl-9H-carbazole as donors and benzo/pyrido[1,2,5]thiadiazole as peripheral acceptors were designed, synthesized and characterized. O

Aromaticity-controlled thermal stability of photochromic systems based on a six-membered ring as ethene bridges: Photochemical and kinetic studies

Three photochromic compounds-2-butyl-5,6-bis[5-(4-methoxyphenyl)-2- methylthiophen-3-yl]-1 H-benzo[de]isoquinoline-1,3(2 H)-dione (BTE-NA), 4,5-bis[5-(4-methoxyphenyl)-2-methylthiophen-3-yl]benzo[c][1,2,5]thiadiazole (BTA), and BTTA, which contain naphtha