6-Aminobenzothiazole

Product Name6-Aminobenzothiazole
CAS533-30-2
MFC7H6N2S
MW150.2
EINECS208-559-4
MOL File533-30-2.mol

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
InChI	1S/C7H6N2S/c8-5-1-2-6-7(3-5)10-4-9-6/h1-4H,8H2
InChIKey	FAYAYUOZWYJNBD-UHFFFAOYSA-N
SMILES	Nc1ccc2ncsc2c1
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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

Yellow solid

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

Uses

6-Aminobenzothiazole is used as pharmaceutical intermediate.

General Description

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

Synthesis

2942-06-5

533-30-2

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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