1,3-BENZOTHIAZOL-5-AMINE Chemical Properties

Melting point:

55 °C

Boiling point:

323.1±15.0 °C(Predicted)

Density 

1.383

storage temp. 

2-8°C(protect from light)

form 

powder

pka

2.44±0.10(Predicted)

color 

Yellow

Water Solubility 

Sparingly soluble in water.(0.26 g/L) (25°C),

InChI

InChI=1S/C7H6N2S/c8-5-1-2-7-6(3-5)9-4-10-7/h1-4H,8H2

InChIKey

UJZYHMZRXGNDFB-UHFFFAOYSA-N

SMILES

S1C2=CC=C(N)C=C2N=C1

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-36-22

Safety Statements 

22-26-36/37/39

RIDADR 

2811

Hazard Note 

Harmful

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

2934208090

1,3-BENZOTHIAZOL-5-AMINE Usage And Synthesis

Uses

It is used as pharmaceutical intermediate. Benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor.

Synthesis

General procedure for the synthesis of 1,3-benzothiazol-5-amine from 5-nitrobenzothiazole: A mixture of 5-nitro-1,3-benzothiazole (5.1 g, 11 mmol) and stannous(II) chloride dihydrate (8.6 g, 38 mmol) in 2-propanol (30 mL) was heated to reflux and the reaction was sustained for 24 hr. Upon completion of the reaction, the cooled reaction mixture was poured into an ice/water mixture (85 mL) and the pH was adjusted with sodium hydroxide solution to 7. Subsequently, the mixture was extracted with ethyl acetate (3 x 50 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. The dried organic phase was filtered and concentrated and the residue was purified by silica gel column chromatography (eluent ratio 1:1 hexane:ethyl acetate) to afford the target product 1,3-benzothiazol-5-amine (820 mg, 52% yield). The product was characterized by LHNMR (CDCl3): δ 6.85 (1H, dd, J=2.3,8.6 Hz), 7.40 (1H, d, J=2.1 Hz), 7.66 (1H, d, J=8.4 Hz), 8.90 (1H, s).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 957 - 971
[2] Catalysis Letters, 2014, vol. 144, # 7, p. 1258 - 1267
[3] Patent: WO2005/28445, 2005, A2. Location in patent: Page/Page column 28
[4] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22
[5] Chem.Abstr., 1951, p. 609

1,3-BENZOTHIAZOL-5-AMINE(1123-93-9)Related Product Information

• 2-METHYL-5-NITROBENZOTHIAZOLE
• 5-NITRO-BENZOTHIAZOL-2-YLAMINE
• 2-Chloro-5-benzothiazolamine
• 1,3-BENZOTHIAZOL-5-AMINE
• 5-AMINO-2-METHYLBENZOTHIAZOLE
• 5-Nitrobenzothiazole-2-thiol
• 5-NITROBENZOTHIAZOLE
• 4-BROMO-BENZOTHIAZOL-5-YLAMINE
• Benzothiazole, 2-chloro-5-nitro- (7CI,8CI,9CI)
• N-METHYL-1,3-BENZOTHIAZOL-2-AMINE HYDROBROMIDE
• 4,6-Dichloro-1,3-benzothiazol-2-amine
• 4-(trifluoromethyl)benzothiazol-2-amine
• benzothiazol-6-amine
• 2-(METHYLTHIO)-1,3-BENZOTHIAZOL-6-AMINE
• 1,3-BENZOTHIAZOL-2-AMINE
• 2-AMINO-4,6-DIFLUOROBENZOTHIAZOLE
• Pramipexole
• 2,1,3-BENZOTHIADIAZOL-5-AMINE