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)

Flash point:

203 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Solubility in methanol almost transparent.

form 

Low Melting Solid

pka

0.37±0.33(Predicted)

color 

Colorless to white to pale yellow

BRN 

112408

InChI

InChI=1S/C6H4N2S/c1-2-4-6-5(3-1)7-9-8-6/h1-4H

InChIKey

PDQRQJVPEFGVRK-UHFFFAOYSA-N

SMILES

N1=C2C=CC=CC2=NS1

CAS DataBase Reference

273-13-2(CAS DataBase Reference)

NIST Chemistry Reference

2,1,3-Benzothiadiazole(273-13-2)

EPA Substance Registry System

2,1,3-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 

Yes

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,1,3-Benzothiadiazole Usage And Synthesis

Chemical Properties

Colorless to light brown solid

Uses

The 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.

Uses

2,1,3-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

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(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