2-AMINO-BENZOTHIAZOL-6-OL Chemical Properties

Melting point:

243-250℃

Boiling point:

394.6±34.0 °C(Predicted)

Density 

1.553±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

8.69±0.40(Predicted)

form 

solid

Appearance

Off-white to gray Solid

InChI

InChI=1S/C7H6N2OS/c8-7-9-5-2-1-4(10)3-6(5)11-7/h1-3,10H,(H2,8,9)

InChIKey

VLNVTNUTGNBNBY-UHFFFAOYSA-N

SMILES

S1C2=CC(O)=CC=C2N=C1N

CAS DataBase Reference

26278-79-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

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

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2934208090

2-AMINO-BENZOTHIAZOL-6-OL Usage And Synthesis

Uses

2-Amino-6-hydroxybenzothiazole is a reagent used in the chemical synthesis of new benzothiazole derivatives with anti proliferative and antiiconvulsant activity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 4103, 1970 DOI: 10.1021/jo00837a003

Synthesis

General procedure for the synthesis of 2-amino-6-hydroxybenzothiazole from 1-(4-hydroxyphenyl)thiourea: 1-(4-hydroxyphenyl)thiourea (5 g, 29.7 mmol) was dissolved in chloroform (30 mL) in a 100 mL two-necked round-bottomed flask fitted with a stirrer. The chloroform (15 mL) solution of bromine (5 g, 29.7 mmol) was transferred to a dropping funnel and slowly added dropwise to the reaction mixture under stirring while controlling the reaction temperature to be lower than 5 °C. After the dropwise addition, the reaction was continued with stirring for 4-6 hours. Subsequently, the reaction mixture was refluxed on a water bath until no more hydrogen bromide gas escaped. After completion of the reaction, the resulting solid was treated with ice water and filtered. The filtrate was neutralized with ammonia solution and the precipitated white precipitate was filtered and washed with water. Finally, the product 2-amino-6-hydroxybenzothiazole was recrystallized from ethanol to give a white solid powder (4 g, 80% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6, 400 MHz): δ 9.10 (s, 1H, -OH), 7.13 (d, J = 8.4 Hz, 1H, ArH, C5-H), 7.06 (s, 2H, -NH2), 7.01 (d, J = 2.4 Hz, 1H, ArH, C4-H), 6.65 (dd, J = 2.6 , 8.6 Hz, 1H, ArH, C7-H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3460 - 3463
[2] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9814 - 9824

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