2207-32-1

Basic information

• Product Name: 5-CHLOROBENZO-2,1,3-THIADIAZOLE
• Synonyms: 5-CHLOROBENZO-2,1,3-THIADIAZOLE;5-CHLORO-2,1,3-BENZOTHIADIAZOLE;2,1,3-benzothiadiazole, 5-chloro-;5-chloropiazthiole;6-chloro-2,1,3-benzothiadiazole;5-Chlorobenzo[c][1,2,5]thiadiazole;5-Chlorobenzothiadiazole;NSC 139785
• CAS NO: 2207-32-1
• Molecular Formula: C₆H₃ClN₂S
• Molecular Weight: 170.62
• Product Categories: API intermediates
• Mol File: 2207-32-1.mol

Chemical Properties

• Melting Point: 55-57°C
• Boiling Point: 248℃
• Flash Point: 104℃
• Appearance: /
• Density: 1.531
• Vapor Pressure: 0.039mmHg at 25°C
• Refractive Index: 1.71
• Storage Temp.: Room temperature.
• PKA: -0.73±0.36(Predicted)
• CAS DataBase Reference: 5-CHLOROBENZO-2,1,3-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROBENZO-2,1,3-THIADIAZOLE(2207-32-1)
• EPA Substance Registry System: 5-CHLOROBENZO-2,1,3-THIADIAZOLE(2207-32-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-22
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 2207-32-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLOROBENZO-2,1,3-THIADIAZOLE is used as a building block for the development of new drugs due to its unique chemical structure and potential biological activity. It can be incorporated into drug molecules to enhance their therapeutic properties and target specific diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 5-CHLOROBENZO-2,1,3-THIADIAZOLE is used as a precursor in the synthesis of various agrochemicals, such as pesticides and herbicides. Its chemical properties make it suitable for creating effective and targeted agrochemicals.
Used in Materials Science:
5-CHLOROBENZO-2,1,3-THIADIAZOLE is used in materials science for its potential applications in the development of dyes and pigments. Its unique structure allows for the creation of compounds with specific color properties and stability.
Used as a Corrosion Inhibitor:
5-CHLOROBENZO-2,1,3-THIADIAZOLE has been investigated for its properties as a corrosion inhibitor. It can be used to protect metal surfaces from corrosion, extending the lifespan of materials used in various industries.
Used in Organic Electronic Materials:
5-CHLOROBENZO-2,1,3-THIADIAZOLE is also a potential component in the development of organic electronic materials, such as organic light-emitting diodes (OLEDs) and organic solar cells. Its electronic properties make it a promising candidate for improving the performance and efficiency of these devices.

InChI:InChI=1/C6H3ClN2S/c7-4-1-2-5-6(3-4)9-10-8-5/h1-3H

Upstream product

• 222851-56-1 N-phenylsulfinylamine 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 108799-22-0 benzo[1,2,5]thiadiazole-5-sulfonic acid; barium salt 

Downstream Products

• 2274-89-7 5-chloro-4-nito-2,1,3-benzothiadiazole 
• 13315-65-6 4,5,6,7-Tetrachlor-2,1,3-benzothiadiazol 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 30536-19-7 4-amino-5-chloro-2,1,3-benzothiadiazole 
• 1435520-79-8 3-(4-(benzo[c][1,2,5]thiadiazol-5-yloxy)phenyl)propanenitrile 
• 1753-76-0 5-Methoxy-2,1,3-benzothiadiazol 
• 768-10-5 benzo[1,2,5]thiadiazol-5-ol 

Relevant articles and documents

Chlorination of Low-Band-Gap Polymers: Toward High-Performance Polymer Solar Cells

Halogenation is an effective way to tune the energy levels of organic semiconducting materials. To date, fluorination of organic semiconducting materials to fabricate polymer solar cells (PSCs) has been used far more than chlorination; however, fluorine exchange reactions suffer from low yields and the resulting fluorinated polymer always comes with a higher price, which will greatly hinder their commercial applications. Herein, we designed and synthesized a series of chlorinated donor-acceptor (D-A) type polymers, in which benzo[1,2-b:4,5-b]dithiophene and chlorinated benzothiadiazole units are connected by thiophene π-bridges with an asymmetric alkyl chain. These chlorinated polymers showed deep highest occupied molecular orbital (HOMO) energy levels, which promoted the efficiency of their corresponding PSCs by increasing the device open circuit voltage. The asymmetric alkyl chain on the thiophene moieties gave the final polymer sufficient solubility for solution processing and strong π-π stacking in films allowed for high mobility. Although the introduction of a large Cl atom increased the torsion angle of the polymer backbone, the chlorinated polymers maintained a favorable backbone orientation in blend films for efficient PSC application. These factors contributed to respectable device performances from thick-film devices, which showed PCEs as high as 9.11% for a 250-nm-thick active layer. These results demonstrate that chlorination is a promising method to fine-tune the energy levels of conjugated polymers, and chlorinated benzothiadiazole may be a versatile building block in materials for efficient solar energy conversion.

Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity

The delocalization of electron density upon tautomerization of a proton across a conjugated bridge can alter the strength of hydrogen bonds. This effect has been dubbed resonance-assisted hydrogen bonding (RAHB) and plays a major role in the energetics of the tautomeric equilibrium. The goal of this work was to investigate the role that π-delocalization plays in the stability of RAHBs by engaging other isomerization processes. Similarly, acid-base chemistry has received little experimental attention in studies of RAHB, and we address the role that acid-base effects play in the tautomeric equilibrium. We find that π-delocalization and the disruption of adjacent aromatic rings is the dominant effect in determining the stability of a RAHB.

Highly stable and bright fluorescent chlorinated polymer dots for cellular imaging

Chlorinated organic materials have drawn much attention and have been applied in various fields due to their intriguing properties such as easy accessibility with low cost, high capability to hold electron density, and “heavy-atom effect”. In this work, a

Chlorination: Vs. fluorination: A study of halogenated benzo [c] [1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging

Red/near-infrared organic dyes are becoming increasingly widespread in biological applications. However, designing these dyes with long-wavelength emission, large Stokes shifts, and high fluorescence quantum efficiency is still a very challenging task. In this work, five donor-acceptor (D-A) red/near-infrared fluorophores based on different chlorinated/fluorinated benzo[c][1,2,5]thiadiazole units are designed and synthesized. The photophysical, theoretical calculations, and electrochemical properties explored in this study have proved that the introducing of chlorine atoms will lead to a lower HOMO level, stronger steric hindrance, and a relatively lower quantum yield in solutions. When the organic dots are fabricated, the chlorinated dots demonstrate much higher fluorescence quantum yield, larger Stokes shift, and better photostability than that of the fluorinated dots. After labeling A549 cells, all the chlorinated/fluorinated dots exhibit high red emission intensities. All these results indicated that the subtle change in the halogen atom of the benzo[c][1,2,5]thiadiazole unit is a unique method to tune the photophysical properties of those materials, and also provides good guidelines to design highly efficient red/near-infrared molecules for cellular imaging applications.

METHOD OF MANUFACTURING 3, 3' , 4, 4'-TETRAAMINOBIPHENYL

An object of the present invention is to provide an efficient method of manufacturing 3,3′,4,4′-tetraaminobiphenyl with a smaller number of steps. The manufacturing method of 3,3′,4,4′-tetraaminobiphenyl includes reacting the amino groups of a 4-halo-o-phenylenediamine with an inorganic sulfur compound to lead to a 5-halo-2,1,3-benzothiadiazole, subsequently coupling two molecules of the benzothiadiazole together to form a 5,5′-bis(2,1,3-benzothiadiazole) and then deprotecting the amino groups to yield 3,3′,4,4′-tetraaminobiphenyl.