ChemicalBook--->CAS DataBase List--->24134-09-6

24134-09-6

24134-09-6 Structure

24134-09-6 Structure
IdentificationBack Directory
[Name]

5-BROMO-1,2-DIMETHYL-1H-IMIDAZOLE
[CAS]

24134-09-6
[Synonyms]

4-BROMO-1,5-DIMETHYLIMIDAZOLE
5-broMo-1,2-diMethyliMidazole
5-BROMO-1,2-DIMETHYL-1H-IMIDAZOLE
1,2-Dimethyl-5-bromo-1H-imidazole
1H-IMidazole,5-broMo-1,2-diMethyl-
5-Bromo-1,2-dimethyl-1H-imidazole 96%
5-Bromo-1,2-dimethyl-1H-imidazole ,97%
[Molecular Formula]

C5H7BrN2
[MDL Number]

MFCD06659905
[MOL File]

24134-09-6.mol
[Molecular Weight]

175.03
Chemical PropertiesBack Directory
[Melting point ]

91 °C
[Boiling point ]

266.6±13.0 °C(Predicted)
[density ]

1.58±0.1 g/cm3(Predicted)
[storage temp. ]

Keep Cold
[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 DataBack Directory
[Symbol(GHS) ]

Flame (GHS02)Corrosion (GHS05)
GHS02,GHS05
[Signal word ]

Danger
[Hazard statements ]

H226-H314
[Precautionary statements ]

P280-P305+P351+P338-P310
[Hazard Codes ]

C,Xn
[Risk Statements ]

22
[Hazard Note ]

Corrosive/Keep Cold
[HS Code ]

2933299090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium hydroxide-->Ethyl acetate-->Dichloromethane-->Bromine-->Sodium bicarbonate-->N-Bromosuccinimide-->Sodium sulfite-->2-Methylimidazole-->Methyl p-toluenesulfonate-->1,2-Dimethylimidazole
Spectrum DetailBack Directory
[Spectrum Detail]

5-BROMO-1,2-DIMETHYL-1H-IMIDAZOLE(24134-09-6)1HNMR
Hazard InformationBack Directory
[Synthesis]

1,2-Dimethylimidazole

1739-84-0

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

24134-09-6

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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