5-BROMO-2-METHYLBENZOTHIAZOLE Chemical Properties

Melting point:

79°C

Boiling point:

170 °C / 10mmHg

Density 

1.644±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

pka

1.14±0.10(Predicted)

form 

powder to crystal

color 

White to Orange to Green

InChI

InChI=1S/C8H6BrNS/c1-5-10-7-4-6(9)2-3-8(7)11-5/h2-4H,1H3

InChIKey

OLQKNZNXLBILDD-UHFFFAOYSA-N

SMILES

S1C2=CC=C(Br)C=C2N=C1C

CAS DataBase Reference

63837-11-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

2934208090

5-BROMO-2-METHYLBENZOTHIAZOLE Usage And Synthesis

Chemical Properties

Light yellow solid

Synthesis

Step A: Sodium nitrite (0.9 g, 13 mmol) was added in batches to a suspension of 2-methyl-5-aminobenzothiazole dihydrochloride (2.0 g, 8 mmol) in hydrobromic acid (24 ml) at 0 °C. The resulting mixture was slowly added dropwise to a solution of copper (I) bromide (4.0 g, 14 mmol) in hydrobromic acid (50 ml) at 0°C. The reaction mixture was stirred continuously at 0 °C for 2 h before the reaction was terminated by the addition of water. The pH of the reaction mixture was adjusted to 9 with aqueous ammonium hydroxide and subsequently extracted with ethyl acetate. The organic layers were combined, dried with magnesium sulfate and purified by column chromatography (eluent ratio 9:1 heptane/ethyl acetate) to afford the target product 2-methyl-5-bromobenzothiazole (1.0 g, 52% yield, 82% GC purity). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 8.12 (d, J=1.8 Hz, 1H), 8.02 (dd, J=8.4,1.5 Hz, 1H), 7.56 (dd, J=8.7,2.1 Hz, 1H), 2.81 (s, 3H).

References

[1] Patent: US2006/52378, 2006, A1. Location in patent: Page/Page column 108

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