2-AMINO-4-BROMOBENZOTHIAZOLE Chemical Properties

Melting point:

182-184 °C(Solv: ethanol (64-17-5))

Boiling point:

366.8±34.0 °C(Predicted)

Density 

1.836±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

2.14±0.10(Predicted)

color 

Off-white

InChI

InChI=1S/C7H5BrN2S/c8-4-2-1-3-5-6(4)10-7(9)11-5/h1-3H,(H2,9,10)

InChIKey

FVMCARDEQKVVIS-UHFFFAOYSA-N

SMILES

S1C2=CC=CC(Br)=C2N=C1N

Safety Information

HS Code 

29342000

2-AMINO-4-BROMOBENZOTHIAZOLE Usage And Synthesis

Chemical Properties

White solid

Synthesis

General procedure for the synthesis of 2-amino-4-bromobenzothiazole from o-bromophenylthiourea: (II) LiBr (1.5 eq.) was added to a solution of acetic acid (50 ml) of the product (5 g, 21.64 mmol) obtained in step (I) at room temperature. Subsequently, the reaction mixture was cooled to 0 °C and bromine (1 eq.) was slowly added. After addition, the reaction mixture was warmed to 85 °C and the reaction was continuously stirred for 16 hours. Upon completion of the reaction, the reaction was quenched with sodium thiosulfate solution and the mixture was diluted with ethyl acetate. The organic phase was separated and washed sequentially with water and saturated NaCl solution. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: ethyl acetate/hexane mixed solvent) to afford the target product 2-amino-4-bromobenzothiazole in 68.3% yield.

References

[1] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148
[2] Patent: WO2010/142402, 2010, A1. Location in patent: Page/Page column 114-115
[3] Journal fuer Praktische Chemie (Leipzig), 1974, vol. 316, p. 154 - 158
[4] Journal of the Chemical Society [Section] C: Organic, 1969, p. 268 - 272

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