ChemicalBook > CAS DataBase List > 4-BROMO-1-METHYL-1H-IMIDAZOLE

4-BROMO-1-METHYL-1H-IMIDAZOLE

Application

Product Name: 4-BROMO-1-METHYL-1H-IMIDAZOLE
CAS No.: 25676-75-9
Chemical Name: 4-BROMO-1-METHYL-1H-IMIDAZOLE
Synonyms: 4-BROMO-1-METHYLIMIDAZOLE;1-Methyl-4-bromoimidazole;4-BROMO-1-METHYL IMDIAZOLE;4-Bromo-1-methyl-1H-imdazole;4-BROMO-1-METHYL-1H-IMIDAZOLE;1H-Imidazole, 4-bromo-1-methyl-;4-BroMo-1-Methyl-1H-iMidazole 95%;4-Bromo-1-methyl-1H-imidazole
CBNumber: CB0772114
Molecular Formula: C4H5BrN2
Formula Weight: 161
MOL File: 25676-75-9.mol

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4-BROMO-1-METHYL-1H-IMIDAZOLE Property

Boiling point:: 91-93/0.1mm
Density: 1.614 g/mL at 25 °C
refractive index: n20/D1.545
Flash point:: >110℃
storage temp.: Inert atmosphere,2-8°C
pka: 4.26±0.61(Predicted)
form: liquid
color: Light brown to brown
InChI: InChI=1S/C4H5BrN2/c1-7-2-4(5)6-3-7/h2-3H,1H3
InChIKey: IOTSLMMLLXTNNH-UHFFFAOYSA-N
SMILES: C1N(C)C=C(Br)N=1
CAS DataBase Reference: 25676-75-9

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Safety

Risk Statements: 36/37/38
Safety Statements: 26-36/37/39
WGK Germany: 2
Hazard Note: Harmful/Keep Cold
HS Code: 2933299090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 711292
Product name: 4-Bromo-1-methyl-1H-imidazole
Purity: 95%
Packaging: 1g
Price: $95.7
Updated: 2025/07/31

TRC

Product number: B697175
Product name: 4-Bromo-1-methyl-1H-imidazole
Packaging: 250mg
Price: $55
Updated: 2021/12/16

Apolloscientific

Product number: OR1221
Product name: 4-Bromo-1-methyl-1H-imidazole
Purity: 98%
Packaging: 1g
Price: $114
Updated: 2021/12/16

SynQuest Laboratories

Product number: 3H32-9-F9
Product name: 4-Bromo-1-methyl-1H-imidazole
Purity: 98%
Packaging: 1g
Price: $125
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB138831
Product name: 4-Bromo-1-methyl-1H-imidazole
Packaging: 1g
Price: $140
Updated: 2021/12/16

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4-BROMO-1-METHYL-1H-IMIDAZOLE Chemical Properties,Usage,Production

Application

4-Bromo-1-methyl-1H-imidazole is an organic synthesis intermediate and a pharmaceutical intermediate that can be used in laboratory research and development processes and chemical production processes.

Synthesis

1003-91-4

25676-75-9

1. To a solution of N-methylimidazole (1.64 g, 19.97 mmol) and sodium acetate (25 g, 300 mmol) in acetic acid (180 mL) was added dropwise a solution of bromine (9.6 g, 60.07 mmol) in acetic acid at room temperature. The reaction mixture was stirred at room temperature for 2.5 hours. Upon completion of the reaction, the acetic acid was removed by vacuum distillation and the residue was suspended in 500 mL of water and stirred for 10 minutes at room temperature. The precipitate was collected by filtration, washed with water and dried under high vacuum to afford 2,4,5-tribromo-1-methyl-1H-imidazole (1.82 g, 29% yield, part of the product was retained in the mother liquor) as a light yellow powder, which could be used in the next reaction without further purification. 2. 2,4,5-tribromo-1-methyl-1H-imidazole (1.82 g, 5.71 mmol) was suspended in 45 mL of water, sodium sulfite (13 g, 103 mmol) was added, and the reaction mixture was stirred under rapid reflux for 24 hours. After cooling to room temperature, the organic phase was extracted with ether (3 x 75 mL), the organic phases were combined, dried with magnesium sulfate, filtered and concentrated to give 1.61 g of a mixture of tribromo, dibromo and monobromo imidazole. 3. The above mixture was dissolved in 15 mL of a 3:1 water/acetic acid solvent mixture, the same amount of sodium sulfite was added, placed in a sealed container and heated at 130 °C for 60 hours. After cooling to room temperature, the pH of the reaction mixture was adjusted to 9-10 with 2N sodium hydroxide solution. the organic phase was extracted with ether (3 x 50 mL), the organic phases were combined, dried with magnesium sulfate, filtered and concentrated to give the crude 4-bromo-1-methyl-1H-imidazole (571 mg, yield about 62%), which could be used for the next reaction without further purification. 4. using 4-bromo-1-methyl-1H-imidazole (571 mg, about 3.53 mmol) as a raw material, 4-butyl-1-methyl-1H-imidazole (95 mg, 22% yield) was synthesized by substituting hexylboronic acid with propylboronic acid (372 mg, 4.24 mmol) according to the method of Example 3.1 , which was used in the next reaction without further purification. 5. Butyllithium (0.34 mL, 2.5 M hexane solution) was added dropwise to 2 mL of anhydrous tetrahydrofuran solution of diisopropylamine (0.13 mL, 0.918 mmol) at -0 °C. The reaction was carried out with stirring over a period of 20 min. With stirring, the solution was warmed to -20 °C over 20 min and then cooled to -78 °C. A 2 mL solution of anhydrous tetrahydrofuran of 4-butyl-1-methyl-1H-imidazole (95 mg, 0.765 mmol) was added dropwise and stirred for 40 min at -78 °C. Dimethylformamide (0.24 mL, 3.06 mmol) was added, stirred and warmed to room temperature. The reaction mixture was poured into 15 mL of 1N hydrochloric acid and stirred for 5 minutes. The pH was adjusted to 7-8 with saturated sodium bicarbonate solution, the organic phase was extracted with dichloromethane (3 x 20 mL), the organic phases were combined, dried with magnesium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with gradient elution (5-50% hexane solution of ethyl acetate) to afford 1-methyl-4-propyl-1H-imidazole-2-carboxaldehyde (9 mg, 8% yield) as an off-white solid, which can be used without further purification.

References

[1] Patent: WO2013/192352, 2013, A1. Location in patent: Page/Page column 117

4-BROMO-1-METHYL-1H-IMIDAZOLE Preparation Products And Raw materials

Raw materials

Preparation Products

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4-BROMO-1-METHYL-1H-IMIDAZOLE Suppliers

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View Lastest Price from 4-BROMO-1-METHYL-1H-IMIDAZOLE manufacturers

Career Henan Chemical Co

Product: 4-BROMO-1-METHYL-1H-IMIDAZOLE 25676-75-9
Price: US $1.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: 10000KGS
Release date: 2020-01-09

25676-75-9, 4-BROMO-1-METHYL-1H-IMIDAZOLERelated Search:

4-BROMO-1-TRITYL-1H-IMIDAZOLE 4-Bromo-1-methyl-1H-imidazole-5-carboxaldehyde 98%,4-BROMO-1-METHYL-1H-IMIDAZOLE-5-CARBOXALDEHYDE 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE 1-BENZYL-2,4,5-TRIBROMO-1H-IMIDAZOLE 4-BROMO-1-METHYL-1H-IMIDAZOLE 2,4,5-TRIBROMO-1-METHYL-1H-IMIDAZOLE 4,5-DIBROMO-1-METHYL-1H-IMIDAZOLE 5-BROMO-1-METHYL-1H-IMIDAZOLE 4-Bromo-2-methyl-1H-imidazole 98%,4-Bromo-2-methyl-1H-imidazole 2-BROMO-4-METHYL-1H-IMIDAZOLE 2-Bromo-1-methyl-1H-imidazole-4-carboxylic acid 4-Bromo-5-methyl-1H-imidazole 2-BROMO-1-METHYL-1H-IMIDAZOLE HYDROCHLORIDE 98,2-Bromo-1-methyl-1H-imidazole hydrochloride 98% 5-Bromo-1-methyl-1H-imidazole-2-carboxaldehyde,5-BROMO-1-METHYL-1H-IMIDAZOLE-2-CARBALDEHYDE,5-Bromo-1-methyl-1H-imidazole-2-carboxaldehyde 98% 2-BROMO-1-METHYL-1H-IMIDAZOLE-4,5-DICARBOXYLIC ACID 2-BROMO-1-METHYL-1H-IMIDAZOLE-4,5-DICARBONITRILE 2-BROMO-1-METHYL-1H-IMIDAZOLE,2-Bromo-1-methyl-1H-imidazole 97% ETHYL 2-(2,4,5-TRIBROMO-1H-IMIDAZOL-1-YL)ACETATE

4-BROMO-1-METHYLIMIDAZOLE

4-BROMO-1-METHYL-1H-IMIDAZOLE

4-BroMo-1-Methyl-1H-iMidazole 95%

1-Methyl-4-bromoimidazole

1H-Imidazole, 4-bromo-1-methyl-

4-Bromo-1-methyl-1H-imdazole

4-BROMO-1-METHYL IMDIAZOLE

4-Bromo-1-methyl-1<i>H</i>-imidazole

25676-75-9

25676-95-9

blocks

Bromides

Imidazoles