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2,2'-BIBENZOTHIAZOLE, with the molecular formula C12H8S2, is a heterocyclic aromatic organic compound known for its applications in various industries. It is characterized by the presence of sulfur atoms in its structure, which contributes to its unique properties and uses.

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  • 4271-09-4 Structure
  • Basic information

    1. Product Name: 2,2'-BIBENZOTHIAZOLE
    2. Synonyms: 2,2'-BIBENZOTHIAZOLE;2-(1,3-benzothiazol-2-yl)-1,3-benzothiazole
    3. CAS NO:4271-09-4
    4. Molecular Formula: C14H8N2S2
    5. Molecular Weight: 268.35672
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 4271-09-4.mol
  • Chemical Properties

    1. Melting Point: 300.5 °C
    2. Boiling Point: 453.8°Cat760mmHg
    3. Flash Point: 220.9°C
    4. Appearance: /
    5. Density: 1.424g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: -0.21±0.10(Predicted)
    10. CAS DataBase Reference: 2,2'-BIBENZOTHIAZOLE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2,2'-BIBENZOTHIAZOLE(4271-09-4)
    12. EPA Substance Registry System: 2,2'-BIBENZOTHIAZOLE(4271-09-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 4271-09-4(Hazardous Substances Data)

4271-09-4 Usage

Uses

Used in Rubber Industry:
2,2'-BIBENZOTHIAZOLE is used as a vulcanization accelerator for the manufacturing of rubber products such as tires and belts. It enhances the process of vulcanization, which is essential for improving the strength, elasticity, and durability of rubber products.
Used in Plastics and Polymers Industry:
2,2'-BIBENZOTHIAZOLE serves as a light stabilizer in plastics and polymers, protecting them from degradation caused by exposure to sunlight and other environmental factors. This helps to maintain the physical properties and appearance of the materials over time.
Used in Dye Production:
2,2'-BIBENZOTHIAZOLE is utilized in the production of dyes due to its ability to impart color to various substrates. Its chemical structure allows it to form stable complexes with other molecules, making it suitable for creating a wide range of colors.
Used in Pharmaceutical Industry:
2,2'-BIBENZOTHIAZOLE is used in the synthesis of certain pharmaceutical compounds, taking advantage of its unique chemical properties to develop new drugs with potential therapeutic applications.
However, it is important to note that 2,2'-BIBENZOTHIAZOLE has been found to be moderately toxic, causing irritation to the eyes, skin, and respiratory system in high concentrations. It is also classified as a possible human carcinogen, which necessitates careful handling and regulation of its usage and production to minimize potential health and environmental risks.

Check Digit Verification of cas no

The CAS Registry Mumber 4271-09-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,2,7 and 1 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 4271-09:
(6*4)+(5*2)+(4*7)+(3*1)+(2*0)+(1*9)=74
74 % 10 = 4
So 4271-09-4 is a valid CAS Registry Number.

4271-09-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(1,3-benzothiazol-2-yl)-1,3-benzothiazole

1.2 Other means of identification

Product number -
Other names 2,2'-dibenzothiazolyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4271-09-4 SDS

4271-09-4Relevant articles and documents

Copper-catalyzed dehydrogenative cross-coupling of benzothiazoles with thiazoles and polyfluoroarene

Fan, Shilu,Zhang, Xingang,Chen, Zhao

supporting information, p. 4950 - 4953,4 (2020/09/16)

A copper-catalyzed dehydrogenative cross-coupling of benzothiazoles with thiazoles and polyfluoroarene under mild reaction conditions is described. This protocol provides a straightforward and operationally simple method for the synthesis of the 2,27prime;-linkage of thiazoles and 2-polyfluoroarylthiazoles of interest in life and material sciences.

Copper(II)-catalyzed dehydrogenative cross-coupling between two azoles

Qin, Xurong,Feng, Boya,Dong, Jiaxing,Li, Xiaoyu,Xue, Ying,Lan, Jingbo,You, Jingsong

supporting information, p. 7677 - 7683 (2012/11/06)

The copper(II)-catalyzed dehydrogenative coupling between two different azoles for the preparation of unsymmetrical biazoles has been developed. The current catalytic system can effectively control the chemoselectivity for heterocoupling over homocoupling.

A general method for copper-catalyzed arene cross-dimerization

Do, Hien-Quang,Daugulis, Olafs

supporting information; experimental part, p. 13577 - 13586 (2011/10/10)

A general method for a highly regioselective copper-catalyzed cross-coupling of two aromatic compounds using iodine as an oxidant has been developed. The reactions involve an initial iodination of one arene followed by arylation of the most acidic C-H bon

Reactions of 2-allylthiobenzimidazole, -oxazole, -thiazole, and the isomeric thiones with dichlorocarbene

Ramazanova,Tarakanova,Vagabov,Litvinova,Anisimov

, p. 201 - 206 (2007/10/03)

The reactions of 2-allylthiobenzimidazole, -oxazole, and -thiazole, and the thiones formed from them on heating, with dichlorocarbene have been investigated under phase transfer catalysis conditions.

A new synthesis of chloroheterocycles via metal-halogen exchange between trichloroacetyl derivatives and heteroaromatic lithium and Grignard reagents

Boga, Carla,Del Vecchio, Erminia,Forlani, Luciano,Milanesi, Lilia,Edgardo Todesco, Paolo

, p. 155 - 159 (2007/10/03)

The reaction between 2-lithio derivatives of aromatic azaheterocycles and trichlorocetyl derivatives rapidly produces the corresponding 2-chloro derivatives in high yields through a metal-halogen exchange mechanism. The use of ethyl trichloroacetate can give better results with respect to those obtained with trichloroacetyl chloride, which probably involves dichloroketene formation. The reaction with Grignard reagents is more complex: in fact, 2-benzothiazolylmagnesium chloride with ethyl trichloroacetate or trichloroacetyl chloride gives 2-chlorobenzothiazole together with considerable amounts of ethyl 1,3-benzothiazole-2-carboxylate or 2-benzothiazolyl dichloromethyl ketone, respectively.

Chemical Interactions between 2-Mercaptobenzazoles and ?-Acceptors

Hassan, A. A.,Mohamed, N. K.,El-Tamany, E. H.,Ali, B. A.,Mourad, A. E.

, p. 653 - 662 (2007/10/02)

2-Mercaptobenzazoles (1a-c) interact with several ?-acceptors such as tetracyanoethylene (TCNE), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), 2,3,5,6-tetrachloro-1,4-benzoquinone (CHL), dicyanomethyleneindane-1,3-dione (CNIND), 2,3-dicyano-1,4-naphthoquinone (DCNQ), 9-dicyanomethylene-2,4,7-trinitrofluorene (DTF), and 2,3-dichloro-1,4-naphthoquinone (DCHNQ) via the formation of charge-transfer (CT) complexes to yield various heterocyclic compounds. - Keywords: 2-Mercaptobenzazoles; Molecular interactions; ?-Acceptors

Inter- and Intramolecular Biaryl Couplings Via Cyanocuprate Intermediates

Lipshutz, Bruce H.,Kayser, Frank,Maullin, Nathalie

, p. 815 - 818 (2007/10/02)

Low temperature oxidations of selected higher order cyanocuprates composed of one or two heteroaromatic ligands can be oxidatively coupled in an inter- or intramolecular fashion to afford unsymmetrical biaryls.Non-heteroaromatic systems have also been studied in related intramolecular processes.

REACTION OF TRIHETEROARYLPHOSPHINES WITH ORGANOLITHIUM REAGENTS CONCURRENT LIGAND EXCHANGE AND LIGAND COUPLING

Uchida, Yuzuru,Takaya, Yoshikazu,Oae, Shigeru

, p. 347 - 351 (2007/10/02)

Reaction of tri(2-benzothiazyl)phosphine or tri(2-pyridyl)phosphine with aryl- or heteroaryllithium compounds in THF affords 2,2'-bibenzothiazyl or 2,2'-bipyridyl by ligand coupling in good yields.

LIGAND EXCHANGE AND LIGAND COUPLING VIA THE ?-SULFURANE INTERMEDIATE IN THE REACTION OF ALKYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENTS: CONVENIENT PREPARATION OF 2,2'-BIPYRIDINES

Oae, Shigeru,Kawai, Tsutomu,Furukawa, Naomichi

, p. 123 - 132 (2007/10/02)

The reaction between methyl 2-pyridyl sulfoxide (1) with Grignard reagents afforded 2,2'-bipyridine (2) in moderate yield.The reaction is considered to involve initial ligand exchange to generate 2-pyridylmagnesium halide which in the subsequent step attacks the original sulfoxide to form the ?-sulfurane that undergoes ligand coupling to afford 2.The reaction of t-butyl-2-pyridyl sulfoxide (3) with C6H5MgBr, however, gave only 2-phenylpyridine (4).This may due to steric hindrance to the initial ligand exchange.Formation of 2 is a convenient process for preparation of 2,2'-bipyridines bearing various substituents.

Electrochemical behaviour of 5-(2-benzothiazolyl hydrazono)-1,3-dimethylbarbituric acid

Malik, Wahid U.,Goyal, R. N.,Rajeshwari, Miss

, p. 78 - 82 (2007/10/02)

The electrochemical oxidation and reduction behaviour of 5-(2-benzothiazolyl hydrazono)-1,3-dimethyl barbituric acid has been studied in the pH range 3.0-11.0 at PGE and dropping mercury electrode.The electrochemical oxidation of hydrazones has not previously been studied in detail.The studies reported on hydrazones earlier deal with their reduction.The mechanisms of electrooxidation and electroreduction are suggested on the basis of spectral studies, coulometry and product identification.

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