2255-80-3

Basic information

• Product Name: 4-BROMO-7-METHYL-BENZO[1,2,5]THIADIAZOLE
• Synonyms: 4-BROMO-7-METHYL-BENZO[1,2,5]THIADIAZOLE;4-broMo-7-Methylisothiazolo[4,5-c]pyridine;4-BroMo-7-Methyl-2,1,3-benzothiadiazole;4-bromo-7-methylbenzo[c][1,2,5]thiadiazole
• CAS NO: 2255-80-3
• Molecular Formula: C₇H₅BrN₂S
• Molecular Weight: 229.097
• Mol File: 2255-80-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 139.3-140.3 °C
• Boiling Point: 292.746 °C at 760 mmHg
• Flash Point: 130.848 °C
• Appearance: /
• Density: 1.736 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -0.96±0.50(Predicted)
• CAS DataBase Reference: 4-BROMO-7-METHYL-BENZO[1,2,5]THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-7-METHYL-BENZO[1,2,5]THIADIAZOLE(2255-80-3)
• EPA Substance Registry System: 4-BROMO-7-METHYL-BENZO[1,2,5]THIADIAZOLE(2255-80-3)

Safety Data

• Hazardous Substances Data: 2255-80-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 7, p. 629, 1970 DOI: 10.1002/jhet.5570070324

Upstream product

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• 1457-92-7 4-Methyl-2,1,3-benzothiadiazol 

Downstream Products

• 1393343-59-3 2-{[7-(5-(N,N-diphenyl)aminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile 
• 1393343-60-6 2-{[7-(4-(N,N-diphenyl)aminophenyl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile 
• 1393343-58-2 2-[(7-(4-[N,N-bis(4-methylphenyl)amino]phenyl)-2,1,3-benzothia-diazol-4-yl)methylene]propane-dinitrile 
• 1419639-20-5 2-{[7-(2-fluoro-4-(N,N-di-p-tolyl)aminophenyl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile 
• 1331742-86-9 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile 
• 2255-78-9 4-bromo-7-(bromomethyl)benzo[c][1,2,5]thiadiazole 
• 2101944-50-5 8-bromoquinoxaline-5-carbaldehyde 
• 1360599-43-4 5-bromo-8-methylquinoxaline 

Relevant articles and documents

Organic light-emitting material containing benzo[c][1,2,5]thiadiazole derivative receptor structural unit and application

The invention provides an organic light-emitting material based on a donor-receptor structure of a benzo[c][1,2,5]thiadiazole-4-aldehyde group receptor and a 2-(benzo[c][1,2,5]thiadiazole-4-methylene)malononitrile receptor and application thereof. The organic light-emitting material is a receptor-donor separation system, wherein the receptor is benzo[c][1,2,5]thiadiazole-4-aldehyde or 2-(benzo[c][1,2,5]thiadiazole-4-methylene) malononitrile, and a donor is carbazole and a derivative or benzoxazine and the like. The lowest unoccupied molecular orbital (LUMO) in the material is located in the receptor, and the highest occupied molecular orbital (HOMO) in the material is located in the donor, so that the molecular orbital energy level of the luminescent material can be effectively regulated and controlled through electrical regulation of the receptor structure and the donor. By regulating and controlling the structure of the light-emitting material or the electron donating capability of the donor, the light-emitting color of material molecules can be conveniently regulated. The organic light-emitting material has the characteristic that the light-emitting color is easy to adjust, andcan be used as a light-emitting material for preparing an OLED device.

Surprising characteristics of D-A-type functional dyes by introducing 4-alkoxythiazoles as the donor-unit

In this study, we report on the syntheses of novel donor-acceptor molecules. These new dyes comprised benzo[c][1,2,5]thiadiazole and pendants with one or two 4-alkoxythiazoles as donor parts, which were introduced without Pd-catalyzed cross coupling reactions. The optical and electrochemical properties were studied via absorption, emission spectroscopy and cyclovoltammetric measurements. We experimentally found surprising small band gaps from HOMO to LUMO of 2.4 eV and 2 eV, respectively, which were also investigated using DFT calculations.

Property modulation of benzodithiophene-based polymers via the incorporation of a covalently bonded novel 2,1,3-benzothiadiazole-1,2,4-oxadiazole derivative in their main chain for polymer solar cells

Two new electron accepting monomers (BBOB and BOB) containing two serially connected different electron deficient units, such as 2,1,3-benzothiadiazole and 1,2,4-oxadiazole, were prepared and copolymerized with electron-rich benzodithiophene (BDT) derivative to afford polymers P(BDT-BBOB) and P(BDT-BOB), respectively. The optical band gaps of P(BDT-BBOB) and P(BDT-BOB) are calculated to be 2.32 eV and 1.99 eV, respectively, and their highest occupied molecular energy levels are determined to be -5.31 eV and -5.27 eV, respectively. Each of the newly synthesized polymers, i.e.P(BDT-BBOB) and P(BDT-BOB), is used as an electron donor, along with PC61BM as an electron acceptor, in the preparation of polymer solar cells (PSCs). The PSCs made with the configuration of ITO/PEDOT:PSS/P(BDT-BBOB) or P(BDT-BOB):PC61BM (1 : 2 wt%)/LiF/Al gave a maximum power conversion efficiency (PCE) of 1.76% and 2.46%, respectively, and the device performance was further improved to 3.31% and 4.21%, respectively, by simply treating the photoactive layer of PSCs with isopropyl alcohol. Overall, the opto-electrical and photovoltaic properties of the two polymers are found to be quite dependent on the configuration of the covalently bonded 2,1,3-benzothiadiazole and 1,2,4-oxadiazole units incorporated in the polymer main chain.