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2,1,3-Benzothiadiazole

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CAS:273-13-2
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CAS:273-13-2
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2,1,3-Benzothiadiazole manufacturers

  • 2,1,3-Benzothiadiazole
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  • $10.00 / 1KG
  • 2025-09-25
  • CAS:273-13-2
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  • Purity: 99%
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2,1,3-Benzothiadiazole Basic information
Product Name:2,1,3-Benzothiadiazole
Synonyms:2-Thia-1,3-diaza-2H-isoindene;3,4-Benzo-1,2,5-thiadiazole;Benzisothiadiazole;Benzo[1,2,5]thiadiazole;PIAZTHIOLE;2,1,3-BENZOTHIADIAZOLE;BENZO-2,1,3-THIADIAZOLE;3,4-Benzo-1,2,5-thiodiazol
CAS:273-13-2
MF:C6H4N2S
MW:136.17
EINECS:205-985-2
Product Categories:Medical Intermediates
Mol File:273-13-2.mol
2,1,3-Benzothiadiazole Structure
2,1,3-Benzothiadiazole Chemical Properties
Melting point 42-44 °C (lit.)
Boiling point 206 °C (lit.)
density 1.323 (estimate)
refractive index 1.5300 (estimate)
Fp 203 °F
storage temp. Sealed in dry,Room Temperature
solubility Solubility in methanol almost transparent.
pka0.37±0.33(Predicted)
form Low Melting Solid
color Colorless to white to pale yellow
BRN 112408
InChIInChI=1S/C6H4N2S/c1-2-4-6-5(3-1)7-9-8-6/h1-4H
InChIKeyPDQRQJVPEFGVRK-UHFFFAOYSA-N
SMILESN1=C2C=CC=CC2=NS1
CAS DataBase Reference273-13-2(CAS DataBase Reference)
NIST Chemistry Reference2,1,3-Benzothiadiazole(273-13-2)
EPA Substance Registry System2,1,3-Benzothiadiazole (273-13-2)
Safety Information
Risk Statements 36/37/38
Safety Statements 22-24/25-36/37/39-26
WGK Germany 3
RTECS DM2580000
TSCA TSCA listed
HS Code 29349990
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
2,1,3-Benzothiadiazole Usage And Synthesis
Chemical PropertiesColorless to light brown solid
UsesThe product is used as an industrial solvent, and pharmaceutical intermediates for organic synthesis and used nitrocellulose and other resin, wax, fatty, dyes and other solvents.
Uses2,1,3-Benzothiadiazole is a chemical reagent used in the synthesis of supramolecules as well as the synthesis of benzothiadiazole derivatives via cross coupling.
Reactions 2,1,3-benzothiadiazole undergoes the standard chemistry of aromatic compounds, for example readily forming nitro and chloro derivatives.Under reducing conditions, it can be converted back to the 1,2-diaminobenzene compounds from which they were prepared.
Synthesis Reference(s)The Journal of Organic Chemistry, 27, p. 676, 1962 DOI: 10.1021/jo01049a536
Synthesis
o-Phenylenediamine

95-54-5

2,1,3-Benzothiadiazole

273-13-2

General procedure for the synthesis of 2,1,3-benzothiadiazole from o-phenylenediamine: 1,2-diaminobenzene (3.250 g, 30.05 mmol) and triethylamine (18 mL, 130.0 mmol) were dissolved in dichloromethane (20 mL). A solution of sulfuryl chloride (7.0 mL, 96.00 mmol) in dichloromethane (10 mL) was added dropwise with stirring. After completion of the reaction, the solvent was removed by rotary evaporator and the combined organic layers were concentrated under vacuum to afford the target product 2,1,3-benzothiadiazole (3.956 g, 97% yield). The melting point of the product was 43 °C. 1H NMR (CDCl3, 400 MHz, TMS) δ: 8.04-8.00 (m, 2H), 7.62-7.57 (m, 2H).

References[1] Dyes and Pigments, 2016, vol. 124, p. 268 - 276
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1989, vol. 25, # 11, p. 1303 - 1307
[3] Khimiya Geterotsiklicheskikh Soedinenii, 1989, # 11, p. 1555 - 1558
[4] Tetrahedron, 2005, vol. 61, # 46, p. 10975 - 10982
[5] Tetrahedron Letters, 2005, vol. 46, # 40, p. 6843 - 6846
2,1,3-Benzothiadiazole Preparation Products And Raw materials
Raw materialso-Phenylenediamine-->1,2-Benzoquinone dioxime-->Thionyl chloride-->Triethylamine-->Dichloromethane
Tag:2,1,3-Benzothiadiazole(273-13-2) Related Product Information
2-Mercapto-5-methyl-1,3,4-thiadiazole Benzo[b]thien-2-ylboronic acid 4-Aminobenzo-2,1,3-thiadiazole METHYL BENZO-2,1,3-THIADIAZOLE-5-CARBOXYLATE 4-NITRO-2,1,3-BENZOTHIADIAZOLE 2,1,3-Benzothiadiazole-4-sulphonyl chloride 5,6-DIMETHYLBENZO-2,1,3-THIADIAZOLE 5-CHLORO-N-(4,5-DIHYDR-1H-IMIDAZOL-2-YL)-2,1,3-BENZOTHIADIAZOLE-4-AMINE 4-ISOCYANATO-2,1,3-BENZOTHIADIAZOLE 2,1,3-BENZOXADIAZOL-4-AMINE 1,2,3-Benzothiadiazole-5-carbonyl chloride (9CI) 1,2,3-BENZOTHIADIAZOLE-5-CARBOXYLIC ACID Tizanidine hydrochloride 1,2,3-Benzothiadiazole-5-carboxaldehyde 5-Amino-2,1,3-benzothiadiazole 2,1,3-Benzothiadiazole-5-carbaldehyde 5-Chloro-4-Amino-1,2,3-Benzothiadiazole 5-CHLOROBENZO-2,1,3-THIADIAZOLE