6-Aminobenzothiazole Chemical Properties

Melting point:

87-91 °C (lit.)

Boiling point:

323.1±15.0 °C(Predicted)

Density 

1.2162 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, Methanol (Slightly)

form 

Solid

pka

2.74±0.10(Predicted)

color 

Yellow to Beige

Water Solubility 

Slightly soluble in water.

Merck 

14,425

BRN 

116381

InChIKey

FAYAYUOZWYJNBD-UHFFFAOYSA-N

CAS DataBase Reference

533-30-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39-22

WGK Germany 

3

RTECS 

DL1050200

Hazard Note 

Irritant

HS Code 

29342000

MSDS

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

6-Aminobenzothiazole Usage And Synthesis

Chemical Properties

Yellow solid

Uses

6-Aminobenzothiazole is used as pharmaceutical intermediate.

Uses

6-Aminobenzothiazole may be used in the synthesis of following:

• 1-(6-amino-benzothiazolyl)-3-chloro-5-methoxytriazine
• 6-[(4-N,N-dimethylaminophenyl)diazenyl]benzothiazole
• 6-[(2-hydroxy-1-naphthyl)diazenyl]benzothiazole
• 6-dimethylaminobenzothiazole

General Description

6-Aminobenzothiazole can be prepared from 6-nitrobenzothiazole via sonochemical reduction method.

Synthesis

General procedure for the synthesis of 6-aminobenzothiazole from 6-nitrobenzothiazole: 6-nitrobenzothiazole (6.13 mmol) was dissolved in ethanol (30 mL), and 10% Pd/C catalyst was added (20% of the mass of 6-nitrobenzothiazole was used as catalyst). The mixture was placed in a Parr hydrogenation unit and reacted overnight at 50 psi hydrogen pressure. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under vacuum to remove the solvent. Finally, purification by fast chromatography using a 30%-40% ethyl acetate/hexane gradient elution gave pure 6-aminobenzothiazole.

Purification Methods

It crystallises from aqueous EtOH, pet ether or *C6H6/pet ether. The hydrochloride has m 305o(dec) from dilute HCl, and the picrate has m 185o(dec ) from Me2CO. [Boggust & Cocker J Chem Soc 360 1949, Beilstein 27 III/IV 4884.]

References

[1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 11-12, p. 1834 - 1840
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 19, p. 7002 - 7007
[3] Synthesis, 2005, # 4, p. 600 - 604
[4] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 8726 - 8736
[5] Molecules, 2014, vol. 19, # 1, p. 925 - 939

6-Aminobenzothiazole(533-30-2)Related Product Information

• 2,2'-Dithiobis(benzothiazole)
• Triallylamine
• Dibenzylamine
• Benzothiazole
• Glucosamine
• 2-Mercaptobenzothiazole
• Aminopyrine
• Bis(2-ethylhexyl)amine
• Acetaminophen
• EC 2.6.1.2
• 2-Benzothiazolamine
• 2-Chloro-6-nitrobenzothiazole
• 6-NITRO-2-AMINOBENZOTHIAZOLE
• 2-MERCAPTO-6-NITROBENZOTHIAZOLE
• 6-AMINO-2-METHYLBENZOTHIAZOLE
• 6-aminobenzothiazole-2-thiol,6-Aminobenzothiazole-2(3H)-thione
• 2-(METHYLTHIO)-1,3-BENZOTHIAZOL-6-AMINE
• 6-Nitrobenzothiazole