5-BROMO-1,2-DIMETHYL-1H-IMIDAZOLE Chemical Properties

Melting point:

91 °C

Boiling point:

266.6±13.0 °C(Predicted)

Density 

1.58±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

form 

solid

pka

5.93±0.25(Predicted)

color 

beige

InChI

InChI=1S/C5H7BrN2/c1-4-7-3-5(6)8(4)2/h3H,1-2H3

InChIKey

WIRCWIXZNDCIST-UHFFFAOYSA-N

SMILES

C1(C)N(C)C(Br)=CN=1

CAS DataBase Reference

24134-09-6

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

22

Hazard Note 

Corrosive/Keep Cold

HS Code 

2933299090

5-BROMO-1,2-DIMETHYL-1H-IMIDAZOLE Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-bromo-1,2-dimethylimidazole from 1,2-dimethylimidazole: N-bromosuccinimide (NBS) (169 mg, 0.95 mmol) was added to a solution of dimethylformamide (DMF) (5 mL) of 1,2-dimethyl-1H-imidazole (1a) (96 mg, 1 mmol) at room temperature, and the reaction mixture was to be stirred for 3 hours away from light. After completion of the reaction, the resulting orange-yellow solution was diluted with ethyl acetate (EtOAc) (50 mL) and washed sequentially with 10% aqueous sodium hydroxide (2 x 50 mL), water (50 mL) and saturated saline (50 mL). The aqueous phase was then back-extracted with ethyl acetate (50 mL), and all organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure to give 5-bromo-1,2-dimethylimidazole as colorless crystals (3.78 g, 76% yield).

References

[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 4, p. 597 - 609
[2] Tetrahedron, 2004, vol. 60, # 37, p. 8065 - 8071
[3] Patent: US2014/107097, 2014, A1. Location in patent: Paragraph 0332
[4] Tetrahedron Letters, 2015, vol. 56, # 25, p. 3855 - 3857

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