4-Bromo-1H-imidazole supplier

Name
4-Bromo-1H-imidazole
EINECS
CAS No. 2302-25-2
Article Data18
CAS DataBase
Density 1.904 g/cm³
Solubility Slightly soluble in water.
Melting Point 131-135 °C(lit.)
Formula C₃H₃BrN₂
Boiling Point 324.7 °C at 760 mmHg
Molecular Weight 146.974
Flash Point 150.2 °C
Transport Information UN 2811 6.1/PG 3
Appearance Colorless to beige crystalline flakes or powder
Safety 26-36/37/39-45
Risk Codes 25-36/37/38
Molecular Structure
Hazard Symbols T
Synonyms 1H-Imidazole,4-bromo- (9CI);Imidazole, 4(or 5)-bromo- (6CI,7CI);Imidazole, 4-bromo- (8CI);4(or 5)-Bromoimidazole;4-Bromoimidazole;NSC 227280;NSC54254;
PSA 28.68000
LogP 1.17220

Synthetic route

: 2034-22-2
2,4,5-tribromo-1H-imidazole

: 2302-25-2
4-bromo-1 H-imidazole

Conditions

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;

: 64591-03-3
2,4-dibromo-1H-imidazole

: 2302-25-2
4-bromo-1 H-imidazole

Conditions

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

: 288-32-4
1H-imidazole

A: 2302-30-9
4,5-dibromo-1H-imidazole

B: 2034-22-2
2,4,5-tribromo-1H-imidazole

C: 2302-25-2
4-bromo-1 H-imidazole

Conditions

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%

...Expand

: 288-32-4
1H-imidazole

: 77-48-5
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

A: 2302-25-2
4-bromo-1 H-imidazole

B: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

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

...Expand

: 288-32-4
1H-imidazole

A: 2302-30-9
4,5-dibromo-1H-imidazole

B: 2302-25-2
4-bromo-1 H-imidazole

Conditions

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

: 2302-30-9
4,5-dibromo-1H-imidazole

: 2302-25-2
4-bromo-1 H-imidazole

Conditions

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

: 39870-05-8
4-acetyl pyrimidine

: C3H2BrN2(1-)*K(1+)

A: 2302-25-2
4-bromo-1 H-imidazole

B: C6H5N2O(1-)*K(1+)

Conditions

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

...Expand

: 861362-49-4
5-bromo-1(3)H-imidazole-4-carboxylic acid-(4-bromo-anilide)

30percent hydrobromic acid: 30percent hydrobromic acid

: 2302-25-2
4-bromo-1 H-imidazole

Conditions

Conditions	Yield
at 150℃;

5-bromo-imidazole-carboxylic acid-(4)-<4-bromo-anilide>: 5-bromo-imidazole-carboxylic acid-(4)-<4-bromo-anilide>

: 2302-25-2
4-bromo-1 H-imidazole

Conditions

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

: 64591-03-3
2,4-dibromo-1H-imidazole

aqueous sodium sulfite solution: aqueous sodium sulfite solution

: 2302-25-2
4-bromo-1 H-imidazole

: 2302-30-9
4,5-dibromo-1H-imidazole

: 7732-18-5
water

sodium sulfite: sodium sulfite

: 2302-25-2
4-bromo-1 H-imidazole

...Expand

: 7647-01-0
hydrogenchloride

: 116081-72-2
5-bromo-1(3)H-imidazole-4-sulfonic acid

A: 2302-25-2
4-bromo-1 H-imidazole

B: 7664-93-9
sulfuric acid

Conditions

Conditions	Yield
at 170℃;

...Expand

: 2034-22-2
2,4,5-tribromo-1H-imidazole

: 7732-18-5
water

sodium sulfite: sodium sulfite

A: 288-32-4
1H-imidazole

B: 2302-30-9
4,5-dibromo-1H-imidazole

C: 2302-25-2
4-bromo-1 H-imidazole

D 5-bromo-imidazole-sulfonic acid-(4): 5-bromo-imidazole-sulfonic acid-(4)

...Expand

: 288-32-4
1H-imidazole

: 2302-25-2
4-bromo-1 H-imidazole

Conditions

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

: 2302-25-2
4-bromo-1 H-imidazole

: 108-24-7
acetic anhydride

: 26227-67-8
1-acetyl-4-bromoimidazole

Conditions

Conditions	Yield
for 0.5h;	99%

: 2302-25-2
4-bromo-1 H-imidazole

: 24424-99-5
di-tert-butyl dicarbonate

: 1338257-80-9
4-bromo-imidazole-1-carboxylic acid tert-butyl ester

Conditions

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%

: 2302-25-2
4-bromo-1 H-imidazole

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 898830-80-3
4-bromo-1-(tetramethylsilyl)-1H-imidazole

Conditions

Conditions	Yield
for 6h; Heating;	95%

: 2302-25-2
4-bromo-1 H-imidazole

: 192182-54-0
3,5-dimethoxyphenylboronic acid

: 312583-37-2
4(5)-(3,5-dimethoxyphenyl)-1H-imidazole

Conditions

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%

: 2302-25-2
4-bromo-1 H-imidazole

: (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

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

: 2302-25-2
4-bromo-1 H-imidazole

: 459-64-3
4-methoxybenzenediazonium tetrafluoroborate

: 130749-87-0
4-bromo-2-(4-methoxyphenylazo)imidazole

Conditions

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

: 2302-25-2
4-bromo-1 H-imidazole

: 139911-27-6
4-fluoro-3-methylphenyl boronic acid

: 4-(4-fluoro-3-methylphenyl)-1H-imidazole

Conditions

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%

: 372-48-5
2-fluoropyridine

: 2302-25-2
4-bromo-1 H-imidazole

: 2-(4-bromo-1H-imidazol-1-yl)pyridine

Conditions

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

: 2302-25-2
4-bromo-1 H-imidazole

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 211615-79-1
4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

Conditions

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

: 2302-25-2
4-bromo-1 H-imidazole

: 5720-07-0
4-methoxyphenylboronic acid

: 35512-31-3
4-(4-methoxyphenyl)-1H-imidazole

Conditions

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%

: 2302-25-2
4-bromo-1 H-imidazole

: 4-bromo-1,2,5-trideutero-1H-imidazole

Conditions

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

: 558-30-5
2-methyl-1,2-epoxypropane

: 2302-25-2
4-bromo-1 H-imidazole

: 1-(4-bromo-1H-imidazol-1-yl)-2-methylpropan-2-ol

Conditions

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

: 2302-25-2
4-bromo-1 H-imidazole

: 32316-92-0
naphthalene-2-boronic acid

: 54532-16-0
4(5)-(2-naphthyl)-1H-imidazole

Conditions

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%

4-Bromo-1H-imidazole Specification

The 1H-Imidazole,4-bromo-, with the CAS registry number 2302-25-2, is also known as 4-Bromoimidazole. It belongs to the product categories of Blocks; Bromides; Imidazoles; Imidazol & Benzimidazole; Imidaxoles; Halogenated Heterocycles; Heterocyclic Building Blocks; ImidazolesBuilding Blocks. This chemical's molecular formula is C₃H₃BrN₂ and molecular weight is 146.97. What's more, its systematic name is 5-bromo-1H-imidazole. It is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides.

Physical properties of 1H-Imidazole,4-bromo- are: (1)ACD/LogP: 0.97; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.9; (4)ACD/LogD (pH 7.4): 0.97; (5)ACD/BCF (pH 5.5): 2.75; (6)ACD/BCF (pH 7.4): 3.21; (7)ACD/KOC (pH 5.5): 68.59; (8)ACD/KOC (pH 7.4): 80.12; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 17.82 Å²; (13)Index of Refraction: 1.601; (14)Molar Refractivity: 26.46 cm³; (15)Molar Volume: 77.1 cm³; (16)Polarizability: 10.49×10^-24cm³; (17)Surface Tension: 56.4 dyne/cm; (18)Density: 1.904 g/cm³; (19)Flash Point: 150.2 °C; (20)Enthalpy of Vaporization: 54.42 kJ/mol; (21)Boiling Point: 324.7 °C at 760 mmHg; (22)Vapour Pressure: 0.000457 mmHg at 25°C.

Preparation: this chemical can be prepared by 5-bromo-1-methyl-1H-imidazole at the ambient temperature. This reaction will need solvent dimethylformamide with the reaction time of 6 hours. The yield is about 66%.

1H-Imidazole,4-bromo- can be used to produce 1H-imidazole at the temperature of 20 °C

Uses of of 1H-Imidazole,4-bromo-: it can be used to produce 5-bromo-1-methyl-1H-imidazole at the ambient temperature. It will need reagent N-bromosuccinimide and solvent dimethylformamide with the reaction time of 48 hours. The yeld is about 41%.

1H-Imidazole,4-bromo- can be prepared by 5-bromo-1-methyl-1H-imidazole at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)InChI: InChI=1S/C3H3BrN2/c4-3-1-5-2-6-3/h1-2H,(H,5,6)
(2)InChIKey: FHZALEJIENDROK-UHFFFAOYSA-N
(3)Canonical SMILES: C1=C(NC=N1)Br

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	250mg/kg (250mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES	Toxicology and Applied Pharmacology. Vol. 89, Pg. 175, 1987.

Product Name

4-Bromo-1H-imidazole

Synthetic route

4-Bromo-1H-imidazole Specification

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