2302-25-2

Basic information

• Product Name: 4-Bromo-1H-imidazole
• Synonyms: 4-BROMO-1H-IMIDAZOLE;4-BROMOIMIDAZOLE;4(or5)-bromo-imidazol;4(or5)-bromoimidazole;4-bromo-1h-imidazol;4-bromo-imidazol;4-Bromo-1H-imidazole,98%;4-Bromo-1H-imidazole,97%
• CAS NO: 2302-25-2
• Molecular Formula: C₃H₃BrN₂
• Molecular Weight: 146.97
• Product Categories: blocks;Bromides;Imidazoles;Imidazol&Benzimidazole;Imidaxoles;Halogenated Heterocycles;Heterocyclic Building Blocks;ImidazolesBuilding Blocks;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;alkyl bromide
• Mol File: 2302-25-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 131-135 °C(lit.)
• Boiling Point: 324.7 °C at 760 mmHg
• Flash Point: 150.2 °C
• Appearance: Colorless to beige/Crystalline Flakes or Powder
• Density: 1.904 g/cm³
• Vapor Pressure: 0.000457mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C(protect from light)
• Solubility: soluble in Dimethylformamide
• PKA: 11.70±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-Bromo-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-1H-imidazole(2302-25-2)
• EPA Substance Registry System: 4-Bromo-1H-imidazole(2302-25-2)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-36-45-37/39-28A
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: NI3517450
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 2302-25-2(Hazardous Substances Data)

Usage

Description

4-Bromo-1H-imidazole (4-Br-1H-Im) is a heterocyclic building block that features an imidazole ring and is known for its crystalline structure in the monoclinic space group P21/c. It is characterized by its colorless to beige crystalline flakes or powder appearance.

Uses

Used in Organic Synthesis:
4-Bromo-1H-imidazole is used as an important intermediate for the synthesis of various organic compounds due to its versatile chemical properties and reactivity.
Used in Agrochemicals:
In the agrochemical industry, 4-Bromo-1H-imidazole is utilized as a key building block for the development of new agrochemical products, contributing to its effectiveness in this field.
Used in Pharmaceutical Industry:
4-Bromo-1H-imidazole serves as a valuable intermediate in the pharmaceutical industry, playing a crucial role in the synthesis of various drugs and medicinal compounds.
Used in Dye Industry:
4-Bromo-1H-imidazole is also employed in the dyestuff field, where it is used as a raw material for the production of different types of dyes, leveraging its chemical properties to enhance color and performance.

InChI:InChI=1/C3H3BrN2/c4-3-1-5-2-6-3/h1-2H,(H,5,6)

Synthetic route

2,4,5-tribromo-1H-imidazole (2034-22-2) → 4-bromo-1 H-imidazole (2302-25-2)

Conditions	Yield
With sodium sulfite In water at 110℃; for 6h;	89%
With sodium sulfite In water at 110℃; for 6h;	85%
With water; sodium sulfite
With sodium sulfite Heating;

2,4-dibromo-1H-imidazole (64591-03-3) → 4-bromo-1 H-imidazole (2302-25-2)

Conditions	Yield
With sodium sulfite In water at 100℃; for 1h; Sealed tube; Microwave irradiation; Green chemistry;	71%
With water; sodium sulfite

1H-imidazole (288-32-4) → 4,5-dibromo-1H-imidazole (2302-30-9) + 2,4,5-tribromo-1H-imidazole (2034-22-2) + 4-bromo-1 H-imidazole (2302-25-2)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 48h; Yields of byproduct given;	A n/a B n/a C 41%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 48h;	A 6% B 3% C 32%

1H-imidazole (288-32-4) + 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (77-48-5) → 4-bromo-1 H-imidazole (2302-25-2) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4)

Conditions	Yield
With sulfuric acid In water at 0℃; for 0.0833333h;	A 21% B 33%

1H-imidazole (288-32-4) → 4,5-dibromo-1H-imidazole (2302-30-9) + 4-bromo-1 H-imidazole (2302-25-2)

Conditions	Yield
With potassium (aquo)(2‑chlorobenzoato)oxodiperoxo–tungstate(VI) dihydrate; potassium bromide In water; acetonitrile at 20℃;	A 27% B 16%

4,5-dibromo-1H-imidazole (2302-30-9) → 4-bromo-1 H-imidazole (2302-25-2)

Conditions	Yield
With water; sodium sulfite
With sodium sulfite In water; isopropyl alcohol Reflux; Large scale;	3.6 kg

4-acetyl pyrimidine (39870-05-8) + C3H2BrN2(1-)*K(1+) → 4-bromo-1 H-imidazole (2302-25-2) + C6H5N2O(1-)*K(1+)

Conditions	Yield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;

5-bromo-1(3)H-imidazole-4-carboxylic acid-(4-bromo-anilide) (861362-49-4) + 30percent hydrobromic acid → 4-bromo-1 H-imidazole (2302-25-2)

Conditions	Yield
at 150℃;

5-bromo-imidazole-carboxylic acid-(4)-<4-bromo-anilide> → 4-bromo-1 H-imidazole (2302-25-2)

Conditions	Yield
With hydrogen bromide at 150℃; im Rohr;

2,4-dibromo-1H-imidazole (64591-03-3) + aqueous sodium sulfite solution → 4-bromo-1 H-imidazole (2302-25-2)

4,5-dibromo-1H-imidazole (2302-30-9) + water (7732-18-5) + sodium sulfite → 4-bromo-1 H-imidazole (2302-25-2)

hydrogenchloride (7647-01-0) + 5-bromo-1(3)H-imidazole-4-sulfonic acid (116081-72-2) → 4-bromo-1 H-imidazole (2302-25-2) + sulfuric acid (7664-93-9)

Conditions	Yield
at 170℃;

2,4,5-tribromo-1H-imidazole (2034-22-2) + water (7732-18-5) + sodium sulfite → 1H-imidazole (288-32-4) + 4,5-dibromo-1H-imidazole (2302-30-9) + 4-bromo-1 H-imidazole (2302-25-2) + 5-bromo-imidazole-sulfonic acid-(4)

1H-imidazole (288-32-4) → 4-bromo-1 H-imidazole (2302-25-2)

Conditions	Yield
With N-Bromosuccinimide In water at 28.44℃; Kinetics; Thermodynamic data; Temperature;
With bromine In water at 28.44℃; Kinetics;

4-bromo-1 H-imidazole (2302-25-2) + acetic anhydride (108-24-7) → 1-acetyl-4-bromoimidazole (26227-67-8)

Conditions	Yield
for 0.5h;	99%

4-bromo-1 H-imidazole (2302-25-2) + di-tert-butyl dicarbonate (24424-99-5) → 4-bromo-imidazole-1-carboxylic acid tert-butyl ester (1338257-80-9)

Conditions	Yield
With triethylamine In dichloromethane for 2h;	98%
With dmap In tetrahydrofuran at 25℃; for 1.5h;	95%
With dmap In dichloromethane at 20℃; for 12h;	93%

4-bromo-1 H-imidazole (2302-25-2) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 4-bromo-1-(tetramethylsilyl)-1H-imidazole (898830-80-3)

Conditions	Yield
for 6h; Heating;	95%

4-bromo-1 H-imidazole (2302-25-2) + 3,5-dimethoxyphenylboronic acid (192182-54-0) → 4(5)-(3,5-dimethoxyphenyl)-1H-imidazole (312583-37-2)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride In water; toluene for 96h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	95%

4-bromo-1 H-imidazole (2302-25-2) + (Z)-4-(3-(4-chlorobut-2-en-1-yl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifiuoromethyl)benzonitrile → (Z)-4-(3-(4-(4-bromo-1H-imidazol-1-yl)but-2-en-1-yl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifiuoromethyl)benzonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;	93%

4-bromo-1 H-imidazole (2302-25-2) + 4-methoxybenzenediazonium tetrafluoroborate (459-64-3) → 4-bromo-2-(4-methoxyphenylazo)imidazole (130749-87-0)

Conditions	Yield
With sodium carbonate In water at 0 - 5℃; for 1h;	92%

4-bromo-1 H-imidazole (2302-25-2) + 4-fluoro-3-methylphenyl boronic acid (139911-27-6) → 4-(4-fluoro-3-methylphenyl)-1H-imidazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 150℃; for 0.833333h; Inert atmosphere; Microwave irradiation;	92%

2-fluoropyridine (372-48-5) + 4-bromo-1 H-imidazole (2302-25-2) → 2-(4-bromo-1H-imidazol-1-yl)pyridine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Microwave irradiation;	92%

4-bromo-1 H-imidazole (2302-25-2) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (211615-79-1)

Conditions	Yield
Stage #1: 4-bromo-1 H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 18h; Inert atmosphere;	91.3%
Stage #1: 4-bromo-1 H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃; for 2h;	1.36 g

4-bromo-1 H-imidazole (2302-25-2) + 4-methoxyphenylboronic acid (5720-07-0) → 4-(4-methoxyphenyl)-1H-imidazole (35512-31-3)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; toluene at 110℃; for 66h; Suzuki-Miyaura reaction;	91%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride In water; toluene for 96h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	75%

4-bromo-1 H-imidazole (2302-25-2) → 4-bromo-1,2,5-trideutero-1H-imidazole

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; water-d2 In water-d2 at 100℃; for 1h;	91%

2-methyl-1,2-epoxypropane (558-30-5) + 4-bromo-1 H-imidazole (2302-25-2) → 1-(4-bromo-1H-imidazol-1-yl)-2-methylpropan-2-ol

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 90℃;	90.6%

4-bromo-1 H-imidazole (2302-25-2) + naphthalene-2-boronic acid (32316-92-0) → 4(5)-(2-naphthyl)-1H-imidazole (54532-16-0)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; toluene at 110℃; for 72h; Suzuki-Miyaura reaction;	90%

Upstream product

• 2302-30-9 4,5-dibromo-1H-imidazole 
• 2034-22-2 2,4,5-tribromo-1H-imidazole 
• 64591-03-3 2,4-dibromo-1H-imidazole 
• 288-32-4 1H-imidazole 
• 39870-05-8 4-acetyl pyrimidine 
• 861362-49-4 5-bromo-1⁽³⁾H-imidazole-4-carboxylic acid-(4-bromo-anilide) 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 116081-72-2 5-bromo-1⁽³⁾H-imidazole-4-sulfonic acid 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 

Downstream Products

• 25676-75-9 4-bromo-1-methyl-1H-imidazole 
• 1003-21-0 5-bromo-N-methylimidazole 
• 123914-24-9 diphenylmethanol 
• 130749-87-0 4-bromo-2-(4-methoxyphenylazo)imidazole 
• 123914-25-0 1-cyclohexanol 
• 78892-77-0 4⁽⁵⁾-(p-toluoyl)imidazole 
• 91874-84-9 4⁽⁵⁾-(p-chlorobenzoyl)imidazole 
• 76-84-6 triphenylmethyl alcohol 
• 87941-55-7 4-bromo-1-(triphenylmethyl)-1H-imidazole 
• 61985-32-8 phenyl 4⁽⁵⁾-imidazolyl ketone 
• 106848-38-8 1-benzyl-4-bromo-1H-imidazole 
• 132430-59-2 5-bromo-1-benzyl-1H-imidazole 
• 84396-14-5 4-methoxyphenyl 4⁽⁵⁾-imidazolyl ketone 
• 13189-13-4 1⁽³⁾H-imidazole-4-carboxylic acid anilide 

Relevant articles and documents

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Synthesis, anti-HIV-1 and antiproliferative evaluation of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety

In an effort to synthesize more effective non-nucleoside reverse transcriptase inhibitors (NNRTIs) against the HIV-1 infection, a new series of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety were designed by molecular docking studies, prepared and characterized by spectroscopic techniques. All the synthesized compounds were in vitro evaluated for their inhibitory effect against the HIV-1 replication in the MT-4 cells. Results showed that none of these synthesized compounds displayed any specific anti HIV-1 activity. Surprisingly, these compounds showed high cytotoxicity against MT-4 cells with low selectivity index (50 = 1.3 μM and EC50 = 1.8 μM respectively).

Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium

Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.