288-32-4

Basic information

• Product Name: Imidazole
• Synonyms: 1,3-Dia-zole,Miazole;1H-Imidazol;Formamidine, N,N'-vinylene-;glioksal;IMD;Imidazol;Imidazolin;Imutex
• CAS NO: 288-32-4
• Molecular Formula: C₃H₄N₂
• Molecular Weight: 68.08
• EINECS: 206-019-2
• Product Categories: Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Biochemistry;Reagents for Oligosaccharide Synthesis;Highly Purified Reagents;Other Categories;Zone Refined Products;Buffer;ACS Grade Buffers;ACS Grade;Biological Buffers;Buffers A to Z;Building Blocks;C3 to C8;Chemical Synthesis;Essential Chemicals;Heterocyclic Building Blocks;Imidazoles;Inorganic Salts;Research Essentials;Solutions and Reagents;Intermediate for Propafenone hydrochloride.;2-8°C;Pharmaceutical intermediates
• Mol File: 288-32-4.mol
• Article Data: 211

Chemical Properties

• Melting Point: 88-91 °C(lit.)
• Boiling Point: 256 °C(lit.)
• Flash Point: 293 °F
• Appearance: white/crystalline
• Density: 1.01 g/mL at 20 °C
• Vapor Pressure: <1 mm Hg ( 20 °C)
• Refractive Index: 1.4801
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.1 M at 20 °C, clear, colorless
• PKA: 6.953(at 25℃)
• Water Solubility: 633 g/L (20 ºC)
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with acids, strong oxidizing agents. Protect from moisture.
• Merck: 14,4912
• BRN: 103853
• CAS DataBase Reference: Imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: Imidazole(288-32-4)
• EPA Substance Registry System: Imidazole(288-32-4)

Safety Data

• Hazard Codes: C,Xi,T
• Statements: 36/38-63-34-22-20/21/22-61
• Safety Statements: 26-36/37/39-45-22-36-27-53
• RIDADR: UN 2923 8/PG 3
• WGK Germany: 1
• RTECS: NI3325000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 288-32-4(Hazardous Substances Data)

Usage

chemical properties

Imidazole is between the two nitrogen atoms of five membered heterocyclic compounds containing. The unshared electron pair of 1-bit nitrogen atom in imidazole ring participates in the cyclic conjugation, reduces the electron density of the nitrogen atom, and makes hydrogen of the nitrogen atom easily leave in the form of hydrogen. Therefore imidazole has weak acidity, and can form salt with strong base. The unshared electron pair of 3-bit nitrogen atom in imidazole ring doesn’t participates in the cyclic conjugation, while it occupies the sp2 hybridized orbital, can accept protons, and form salt with strong acid. Alkaline of imidazole is slightly stronger than pyrazole and pyridine. There is tautomerism in the imidazole ring. The hydrogen on the 1-bit nitrogen atom can be transferred to the 3-atom, therefore, imidazole derivatives with same substituent respectively on 4-bit and 5-bit are tautomers. Imidazole is stable to acid, and has antioxidant activity. Imidazole derivatives are widely found in nature, such as histamine, histidine and benzimidazole, etc. There are some interesting reagents in acyl imidazole compounds. For example, 1-acetyl imidazole is a stable acylating agent, after reaction with pyrrole, it becomes 1-acetyl pyrrole. Furthermore, in general, 1-acetyl imidazole can get ketones and aldehydes using Grignard reagent and reducing agent. Reaction of N, N-carbonyldimidazole and carboxyl will get useful reagent acyl imidazole. The relationship between imidazole and natural compounds is very close. For example, pyrimidine ring turns into purine derivatives after condensation. In addition to being like 6-amino purine and guanine the nucleic acid bases, it also exists in the organisms of uric acid, caffeine and theophylline. The catalytic action of imidazole, such as accelerated enzyme hydrolysis, still under study. As the cause of allergic skin, its toxicity is similar todiamine. Rat oral LD501880mg/kg. imidazole structure

Physical characteristics

In nature, there are only imidazole derivatives and no free imidazole. The precipitation from benzene is a colorless crystalline prism, with scents of ammonia. Relative molecular mass 68.08. Relative density 1.0303(101/4℃) . Melting point 89～91℃，boiling point 257℃，165℃～168℃(2.67×103Pa) and 138.2℃(1.60×103Pa). Flash point 145℃. Refractive index 1.4801(101℃). Viscosity 2.696mPa·s(100℃). Slightly soluble in benzene, petroleum ether, soluble in ether, acetone, chloroform and pyridine, easily soluble in water (at normal temperature 70) and ethanol. It appears weak alkaline. As the-NH-bond on 1 bite and-N= bond on 3 bit forms hydrogen bond, the boiling point is quite high; when 1 bit hydrogen is substituted, hydrogen bond cannot be formed, hence the boiling point decreases. As to thermal stability, it rarely dissolves under 250℃ (decomposition temperature is 590℃). It is also very stable to reducing agent and oxidant, but can form stable salt with inorganic acid. Owning some certain aromatic properties, also could get halogenation, nitration, sulfonation and hydroxymethylation in the presence of catalyst. Can be coupled with the heavy nitrogen salt in 2 bit. In addition, due to the =NH (1 bit) connected to the two double bonds, with some of the "acid", it can be replaced by metal to get salt. In addition, 3 bit nitrogen ions have coordination effect on metal ions, which can form chelate compounds. Although it is difficult to restore, but can be combined with the proton to generate cation type with resonance structure, and get of a stable form. Tautomers of imidazole ring are very easy to change, so it is hard to tell isomers on 4 bit or 5 bit. The above information is edited by the Chemicalbook He Liao Pu.

Chemical Properties

Imidazole is a moderately strong base (pKb= 7.0), and a weak acid (pKa= 14.9). Imidazoles substituted with electron-withdrawing groups are stronger acids than imidazole itself; e.g., 4(5)-nitroimidazole has a pKa of 9.3. Imidazole is stable at 400°C, possesses considerable aromatic character, and undergoes the usual electrophilic aromatic substitution reactions. Nitration and sulfonation require, however, far more drastic conditions than the corresponding reactions with benzene. Other substitution reactions of imidazole include halogenation, hydroxymethylation, coupling with aromatic diazonium salts, and carboxylation.

History

Imidazole[288-32-4] was first synthesized in 1858 by Debus from ammonia and glyoxal; it was originally named glyoxalin. The name imidazole was introduced by Hantzsch. Industrial production of imidazole began in the 1950s; a wide range of derivatives is now available in industrial quantities.

Uses

Imidazole is used as a buffer in the range of pH 6.2-7.8. It is also an histamine antagonist. It acts as a chelator and forms complexes with various divalent cations. It is used as a corrosion inhibitor on certain transition metals such as copper. Its derivatives, like polybenzimidazole (PBI), act as fire retardants. It finds application in photography and electronics. Imidazole salts are used as ionic liquids and precursors to stable carbenes. Imidazole derivatives like ketoconazole, miconazole and clotrimazole are involved in the treatment of various systemic fungal infections. It is a part of the theophylline molecule, present in tea leaves and coffee beans, which stimulates the central nervous system.

Application

Imidazole is a versatile heterocycle used in the preparation of various biologically active compounds such as the amino acid histidine and is present in many antifungal medication. It is also used ext ensively as a corrosion inhibitor on transition metals such as copper.It is used in organic synthesis and as an antiirradiationagent. Imidazole has been used:in the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein.in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography.as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cell.

Preparation

Imidazole is formed by reacting glyoxal with formaldehyde in the presence of ammonium acetate in acetic acid. The driving energy is microwave radiation. More generally, this reaction is used to produce substituted imidazoles.Although there had been discoveries of various derivatives of imidazole in 1840, it was first reported in 1858. The synthesis process of imidazole follows the reaction between formaldehyde in ammonia and glyoxal. This process gives low yield of imidazole but it is still used to form imidazole with C-substitution (Wolkenberg et al., 2004).

Definition

ChEBI: Imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole.

General Description

Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.

Health Hazard

It is less toxic relative to pyrrole and otherfive-membered heterocyclic compounds ofnitrogen. Intraperitoneal administration ofimidazole caused somnolence, muscle contractions,and convulsions in mice. Theoral LD50 value in mice is in the range900 mg/kg.

Fire Hazard

Noncombustible solid.

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division. It also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).

Purification Methods

Crystallise imidazole from *benzene, CCl4, CH2Cl2, EtOH, pet ether, acetone/pet ether and distilled de-ionized water. Dry it at 40o under vacuum over P2O5. Distil it at low pressure. It is also purified by sublimation or by zone melting. [Snyder et al. Org Synth Coll Vol III 471 1955, Bredereck et al. Chem Ber 97 827 1964, Caswell & Spiro J Am Chem Soc 108 6470 1986.] 15N-imidazole crystallises from *benzene [Scholes et al. J Am Chem Soc 108 1660 1986]. [Beilstein 23 II 34, 23 III/IV 564, 23/4 V 191.]

InChI:InChI=1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)

Synthetic route

1-(Trimethylsilyl)imidazole (18156-74-6) + 1-phenyl-acetone (103-79-7) → 1H-imidazole (288-32-4) + 1-phenyl-2-trimethylsiloxy-1-propene (43108-63-0)

Conditions	Yield
Ambient temperature; other silylazoles and carbonyl compounds;	A n/a B 100%

tert-butyl 1H-imidazole-1-carboxylate (49761-82-2) → 1H-imidazole (288-32-4)

Conditions	Yield
With water at 100℃; for 0.166667h;	99%
With silica gel In dichloromethane for 0.0333333h; Irradiation;	98%
With water at 150℃; for 2h; Subcritical conditions;	95%

1,1'-carbonyldiimidazole (530-62-1) + benzyl alcohol (100-51-6) → 1H-imidazole (288-32-4) + N-benzyloxycarbonylimidazole (22129-07-3)

Conditions	Yield
In acetonitrile at 25℃; for 12h; Esterification;	A n/a B 97%

1-benzylimidazole (4238-71-5) → 1H-imidazole (288-32-4)

Conditions	Yield
With Na2K-SG(I) In 1,2-dimethoxyethane at 20℃; Inert atmosphere;	96%
With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	92%

formaldehyd (50-00-0) + Glyoxal (131543-46-9) + ammonia (7664-41-7) + ethanolamine (141-43-5) → 1H-imidazole (288-32-4) + 1-(2-Hydroxyethyl)imidazole (1615-14-1)

Conditions	Yield
Stage #1: formaldehyd; ammonia; ethanolamine In water at 25℃; for 1h; Stage #2: Glyoxal; ammonia at 25℃; for 1h; Product distribution / selectivity;	A 2% B 96%

ethanol (64-17-5) + 1,1'-carbonyldiimidazole (530-62-1) → 1H-imidazole (288-32-4) + ethyl 1-imidazolecarboxylate (19213-72-0)

Conditions	Yield
In acetonitrile at 25℃; for 12h; Esterification;	A n/a B 95%
at 20℃;

Glyoxal (131543-46-9) + isobutyraldehyde (78-84-2) → 1H-imidazole (288-32-4) + 2-isopropylimidazole (36947-68-9)

Conditions	Yield
Stage #1: isobutyraldehyde With ammonia In methanol; water at 25℃; for 1h; Stage #2: Glyoxal With ammonia In methanol; water at 25℃; for 2h; Product distribution / selectivity;	A 2 %Chromat. B 95%
With ammonia In water at 25℃; for 1h; Product distribution / selectivity;	A 23 %Chromat. B 56%

2-Amino-2-methyl-1-propanol (124-68-5) + 1,1'-carbonyldiimidazole (530-62-1) → 1H-imidazole (288-32-4) + 4,4-dimethyl-1,3-oxazolidin-2-one (26654-39-7)

Conditions	Yield
In diethyl ether for 0.166667h; Ambient temperature;	A n/a B 94%

2-(1H-imidazol-1-yl)-1-phenylethanone (24155-34-8) → 1H-imidazole (288-32-4)

Conditions	Yield
With magnesium; acetic acid In methanol at 20℃;	93%

formaldehyd (50-00-0) + Glyoxal (131543-46-9) + ammonia (7664-41-7) + 1-amino-2-propene (107-11-9) → 1H-imidazole (288-32-4) + 1-allylimidazole (31410-01-2)

Conditions	Yield
Stage #1: formaldehyd; ammonia; 1-amino-2-propene In water at 25℃; for 1h; Stage #2: Glyoxal; ammonia at 25℃; for 1h;	A 4% B 93%

N-tosylimidazole (2232-08-8) → 1H-imidazole (288-32-4)

Conditions	Yield
With lithium hydroxide; mercaptoacetic acid In N,N-dimethyl-formamide at 20℃; for 2h;	92%
With mercaptoacetic acid; lithium hydroxide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	92%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;	75%
With acetic anhydride In pyridine for 5h; Ambient temperature;

N-(tert-butoxycarbonyl)-L-serine methyl ester (2766-43-0) + 1,1'-carbonyldiimidazole (530-62-1) → 1H-imidazole (288-32-4) + imidazole-1-carboxylic acid 2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl ester

Conditions	Yield
In acetonitrile at 25℃; for 12h; Esterification;	A n/a B 91%

1,1'-bis(imidazolyl)methane (84661-56-3) → 1H-imidazole (288-32-4)

Conditions	Yield
With lithium aluminium tetrahydride; acetic acid for 4.5h;	91%

imidazole-2-thione (872-35-5) → 1H-imidazole (288-32-4)

Conditions	Yield
With dihydrogen peroxide; acetic acid at 25℃; for 0.0166667h;	90%
With 3,3-dimethyldioxirane In methanol; acetone at 25℃; other imidazole derivatives;	81%

lysidine (534-26-9) → 1H-imidazole (288-32-4) + 2-imidazolinecarbonitrile (1092546-18-3) + 2-imidazolinecarboxamide (696650-10-9)

Conditions	Yield
With ammonia; MoO3-Sb2O4-TiO2 at 330℃;	A n/a B n/a C 90%

N-tritylimidazole (15469-97-3) → 1H-imidazole (288-32-4)

Conditions	Yield
With Na2K-SG(I) In tetrahydrofuran at 20℃; Inert atmosphere;	90%

Glyoxal (131543-46-9) + ammonia (7664-41-7) + ethanolamine (141-43-5) + acetaldehyde (75-07-0) → 1H-imidazole (288-32-4) + N-(2'-hydroxyethyl)-2-methylimidazole (1615-15-2)

Conditions	Yield
Stage #1: ammonia; ethanolamine; acetaldehyde In water at 25℃; for 1h; Stage #2: Glyoxal; ammonia at 25℃; for 1h;	A 5% B 89%

salicylaldehyde (90-02-8) + 2-triphenyl(α-carboxymethylene)phosphorane imidazolide (73818-41-4) → 1H-imidazole (288-32-4) + coumarin (91-64-5)

Conditions	Yield
Stage #1: salicylaldehyde With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 2h; Inert atmosphere; Stage #2: 2-triphenyl(α-carboxymethylene)phosphorane imidazolide In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Intramolecular Wittig reaction; Reflux; Inert atmosphere;	A n/a B 85%

1-allylimidazole (31410-01-2) → 1H-imidazole (288-32-4)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); diisobutylaluminium hydride In toluene for 1h; Ambient temperature;	81%
With Na2K-SG(I) In tetrahydrofuran at 20℃; Inert atmosphere;	65%

piperazine (110-85-0) → 1H-imidazole (288-32-4) + 1,4-pyrazine (290-37-9) + 1-methyl-1H-imidazole (616-47-7) + 2-Methylpyrazine (109-08-0) + 2-ethylpyrazine (13925-00-3) + 2-methylimidazole (693-98-1)

Conditions	Yield
Pt-Al2O3-In2O3-Re at 400℃; Product distribution; variation of catalyst, temperature;	A n/a B 78.7% C n/a D 1.6% E 3.5% F n/a

Glyoxal (131543-46-9) + hexamethylenetetramine (100-97-0) → 1H-imidazole (288-32-4)

Conditions	Yield
With ammonium acetate; acetic acid at 106℃; for 0.0583333h; Microwave irradiation;	78%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 1-(2-nitrobenzenesulfonyl)-1H-imidazole → 1H-imidazole (288-32-4) + 1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-2-nitro-benzene

Conditions	Yield
With potassium carbonate In acetonitrile at 50℃;	A 76% B n/a

1-(2-hydroxy-1-naphthyl)ethan-1-one (574-19-6) + 2-triphenyl(α-carboxymethylene)phosphorane imidazolide (73818-41-4) → 1H-imidazole (288-32-4) + 1-methyl-3H-naphtho[2,1-b]pyran-3-one (21568-13-8)

Conditions	Yield
Stage #1: 1-(2-hydroxy-1-naphthyl)ethan-1-one With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 2h; Inert atmosphere; Stage #2: 2-triphenyl(α-carboxymethylene)phosphorane imidazolide In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Intramolecular Wittig reaction; Reflux; Inert atmosphere;	A n/a B 75%

o-hydroxyacetophenone (118-93-4) + 2-triphenyl(α-carboxymethylene)phosphorane imidazolide (73818-41-4) → 1H-imidazole (288-32-4) + 4-methyl-2H-chromen-2-one (607-71-6)

Conditions	Yield
Stage #1: o-hydroxyacetophenone With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 2h; Inert atmosphere; Stage #2: 2-triphenyl(α-carboxymethylene)phosphorane imidazolide In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Intramolecular Wittig reaction; Reflux; Inert atmosphere;	A n/a B 75%

1-benzhydryl-1H-imidazole (7189-67-5) → 1H-imidazole (288-32-4)

Conditions	Yield
With Na2K-SG(I) In tetrahydrofuran at 20℃; Inert atmosphere;	75%

1H-imidazole (288-32-4) + dichloromethane (75-09-2) → 1,1'-bis(imidazolyl)methane (84661-56-3)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide for 13h; Ambient temperature;	100%
With sodium hydroxide; phase transfer catalysis by tetraethylammonium bromide for 16h; Ambient temperature;	96%
With tetrabutylammomium bromide; sodium hydroxide Inert atmosphere; Reflux;	87%

1H-imidazole (288-32-4) + benzoyl chloride (98-88-4) → 1-benzoylimidazole (10364-94-0)

Conditions	Yield
In benzene at 8 - 20℃;	100%
With iodine at 20℃; for 0.233333h; Neat (no solvent);	97.32%
In benzene at 20℃; for 24h;	94%

1H-imidazole (288-32-4) + phenyl isocyanate (103-71-9) → N-phenyl-1H-imidazole-1-carboxamide (33876-94-7)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	100%
In 1,4-dioxane at 0 - 20℃;	87%
In diethyl ether for 3h; Heating;	84%

1H-imidazole (288-32-4) + propyl bromide (106-94-5) → 1-propyl-1H-imidazole (35203-44-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	100%
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: propyl bromide In tetrahydrofuran; mineral oil at 20℃; for 16h;	93%
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; hexane at 20℃; Stage #2: propyl bromide In tetrahydrofuran; hexane at 60 - 65℃; Reflux;	86%

1H-imidazole (288-32-4) + p-Xylylene dichloride (623-25-6) → 1,4-bis(imidazol-l-yl-methyl)benzene (56643-83-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 6h;	100%
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Stage #2: p-Xylylene dichloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h;	100%
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 6h;	100%

1H-imidazole (288-32-4) → 2,4,5-triiodoimidazole (1746-25-4)

Conditions	Yield
With iodine; sodium carbonate In 1,4-dioxane; water at 20℃; for 24h;	100%
With dihydrogen peroxide; iodine In water at 50℃; for 24h; Green chemistry;	97%
With pyridine; iodine; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane for 3h; Ambient temperature;	95%

1H-imidazole (288-32-4) + 2,4-dichloro-6-ethyl-5-nitropyrimidine (52379-63-2) → 6-ethyl-2,4-bis(1H-imidazol-1-yl)-5-nitropyrimidine (156489-94-0)

Conditions	Yield
In acetonitrile for 18h; Ambient temperature;	100%

1H-imidazole (288-32-4) + PVS (5535-48-8) → 1-(2-(phenylsulfonyl)ethyl)-1H-imidazole

Conditions	Yield
In acetonitrile for 2h; Ambient temperature;	100%
Stage #1: 1H-imidazole With o-phenylenebis(diphenylphosphine); potassium tert-butylate; copper(l) chloride In toluene for 0.166667h; Michael Addition; Inert atmosphere; Stage #2: PVS In toluene at 22℃; for 3h; Michael Addition; Inert atmosphere;	99%

1H-imidazole (288-32-4) + 2-fluorobenzonitrile (394-47-8) → 2-imidazol-1-yl-benzonitrile (25373-49-3)

Conditions	Yield
With 1,2,3-Benzotriazole; potassium tert-butylate; copper(l) iodide In dimethyl sulfoxide at 110℃; for 0.5h;	100%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 36h;	97%
With potassium carbonate; trans-1,2-diaminocyclohexane-based copper(II) complex In N,N-dimethyl-formamide at 110℃; for 1.5h;	92%

1H-imidazole (288-32-4) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (101226-33-9)

Conditions	Yield
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran at 0 - 25℃; for 0.5h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 0 - 25℃; for 14h; Inert atmosphere;	100%
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.75h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃;	93%
Stage #1: 1H-imidazole With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 0.5h; Large scale; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In dimethyl sulfoxide at 0 - 15℃; for 16h; Large scale;	90%

1H-imidazole (288-32-4) + benzyl bromide (100-39-0) → 1-benzylimidazole (4238-71-5)

Conditions	Yield
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 4h;	100%
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 25℃; for 3h;	97%
With caesium carbonate at 100℃; for 0.416667h; Microwave irradiation;	90%

1H-imidazole (288-32-4) + 1-oxo-11-(2'-chloroacetyl)-5,11-dihydro-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one (84446-19-5) → 1-oxo-5,11-dihydro-11-imidazol-1'-ylacetyl-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one (84446-11-7)

Conditions	Yield
In toluene at 80℃; for 2h;	100%

1H-imidazole (288-32-4) + ortho-nitrofluorobenzene (1493-27-2) → 1-(2-nitrophenyl)-1H-imidazole (23309-16-2)

Conditions	Yield
With 1,2,3-Benzotriazole; potassium tert-butylate; copper(l) iodide In dimethyl sulfoxide at 110℃; for 0.5h;	100%
With pyridine; potassium carbonate; copper(II) oxide at 115℃; Ullmann Condensation;	96%
With potassium carbonate In acetonitrile for 24h; Heating;	95%

1H-imidazole (288-32-4) + 3-methoxycarbonylbenzyl bromide (1129-28-8) → methyl 3-((1H-imidazol-1-yl)methyl)benzoate (218131-31-8)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 20h;	100%
In N,N-dimethyl-formamide for 8h;	67%
In acetone for 2h; Heating;	55%

1H-imidazole (288-32-4) + ethanol (64-17-5) → N-Ethylimidazole (7098-07-9)

Conditions	Yield
H-Y zeolite at 299.9℃;	100%
calcined Mg-Al layered double hydroxides at 424.85℃; Alkylation;	63%

1H-imidazole (288-32-4) + formaldehyd (50-00-0) + diethylamine (109-89-7) → N-((1H-imidazol-1-yl)methyl)-N-ethylethanamine

Conditions	Yield
With hydrogenchloride for 48h; Ambient temperature;	100%

1H-imidazole (288-32-4) + 1,4-bis(bromomethyl)benzene (623-24-5) → 1,4-bis(imidazol-l-yl-methyl)benzene (56643-83-5)

Conditions	Yield
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: 1,4-bis(bromomethyl)benzene In tetrahydrofuran; mineral oil for 6h; Reflux; Inert atmosphere;	100%
Stage #1: 1H-imidazole With potassium hydroxide In acetonitrile at 20℃; for 2h; Stage #2: 1,4-bis(bromomethyl)benzene In acetonitrile at 20℃; for 1.5h;	88%
With potassium hydroxide In isopropyl alcohol	80%

1H-imidazole (288-32-4) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 1H-imidazole-1-carboxylate (49761-82-2)

Conditions	Yield
With 1-methylimidazolium tetrafluoroborate at 30 - 35℃; for 0.0833333h;	100%
With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.0166667h;	100%
With amberlyst-15 In ethanol at 20℃; for 0.0166667h; chemoselective reaction;	100%

1H-imidazole (288-32-4) + 3,4-dibromophenylsulfonic acid chloride (81903-80-2) → 1-((3,4-dibromophenyl)sulfonyl)-1H-imidazole (224824-30-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 19h;	100%
With sodium carbonate In methanol; chloroform for 22h; Ambient temperature;	34%

1H-imidazole (288-32-4) + (2R,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxy-2-(2-methanesulfonyloxyethyl)pyrrolidine (156441-21-3) → (2R,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxy-2-[2-(imidazol-1-yl)ethyl]pyrrolidine (156441-22-4)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 60℃; for 1h; Alkylation;	100%

1H-imidazole (288-32-4) + phenylboronic acid (98-80-6) → 1-phenylimidazole (7164-98-9)

Conditions	Yield
With [Cu4I4(1,4-diazabicyclo[2.2.2]octane)2]n In methanol at 27℃; for 5h;	100%
With [Cu30I16(5-methyl-4-(p-tolyl)pyrimidine-2-thiolato)12(μ10-S4)] In methanol for 5h; Temperature; Reagent/catalyst; Reflux;	99%
With polystrene supported copper furfural catalyst In methanol at 40℃; for 10h; Inert atmosphere;	99%

1H-imidazole (288-32-4) + tris(pentafluorophenyl)borate (1109-15-5) + triethylamine (121-44-8) → (μ-(1H-imidazolato-κ-N1:κ-N3))hexakis(pentafluorophenyl)di-borate(1-), N,N-diethylethanamine

Conditions	Yield
In toluene for 5h; Heating;	100%
In toluene at 20℃;	91.9%
In toluene to soln. B(C6F5)3 and imidazole in toluene triethylamine in toluene wasadded, react. mixt. was stirred overnight at room temp.; soln. was concd., hexane was added, ppt. was filtered, washed with hexane and dried under reduced pressure; elem. anal.;	91.9%

1H-imidazole (288-32-4) + m-Fluorobenzonitrile (403-54-3) → 3-(1-imidazolyl)benzonitrile (25699-85-8)

Conditions	Yield
potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h;	100%
With tripotassium phosphate "n" hydrate In N,N-dimethyl-formamide at 110℃; for 18h;	50%
With potassium carbonate; N,N-dimethyl-formamide at 100℃; for 48h; Inert atmosphere;	46%
With potassium carbonate In N,N-dimethyl-formamide at 110℃;
potassium carbonate In N,N-dimethyl-formamide

1H-imidazole (288-32-4) + p-nitrobenzene iodide (636-98-6) → 1-(4-nitrophenyl)-1H-imidazole (2301-25-9)

Conditions	Yield
With copper phthalocyanine; sodium hydroxide In dimethyl sulfoxide at 100℃;	100%
With Hippuric Acid; copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 140℃; for 30h; Ullmann coupling reaction;	99%
With caesium carbonate In dimethyl sulfoxide at 110℃; for 1h; Ullmann Condensation;	98%

1H-imidazole (288-32-4) + 4-chlorobenzonitrile (100-00-5) → 1-(4-nitrophenyl)-1H-imidazole (2301-25-9)

Conditions	Yield
With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride at 140 - 145℃; for 24h;	100%
With potassium tert-butylate; trans-1,2-diaminocyclohexane-based copper(II) complex In N,N-dimethyl-formamide at 110℃; for 2h;	99%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 24.5h;	98%

1H-imidazole (288-32-4) + iodobenzene (591-50-4) → 1-phenylimidazole (7164-98-9)

Conditions	Yield
With potassium tert-butylate; copper(I) oxide In N,N-dimethyl-formamide at 80℃; for 24h;	100%
With potassium tert-butylate In toluene at 180℃; for 18h; Ullmann condensation;	100%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 6h; Inert atmosphere;	99%

1H-imidazole (288-32-4) + 1,3-dibromobenzene (108-36-1) → 1,3-bis(1H-imidazol-1-yl)benzene (69506-91-8)

Conditions	Yield
With 1-sulfanyl-2-(dimethylaminomethyl)-3-Me3Si-benzene-Cu(I); potassium carbonate In 1-methyl-pyrrolidin-2-one at 160℃; for 16h;	100%
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 150℃; for 48h;	99%
With copper(l) iodide; dimethylaminoacetic acid; potassium carbonate In dimethyl sulfoxide at 110℃; for 48h; Inert atmosphere;	93%

1H-imidazole (288-32-4) + para-bromoacetophenone (99-90-1) → 4'-(imidazol-1-yl)acetophenone (10041-06-2)

Conditions	Yield
With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride at 140 - 145℃; for 24h;	100%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 24.5h;	99%
With potassium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 110℃; for 24h; Ullmann coupling reaction;	98%

6-(bromoacetyl)-2-butyl-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (871946-66-6) + 1H-imidazole (288-32-4) → 2-butyl-6-(1H-1-imidazolylacetyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (871946-70-2)

Conditions	Yield
In chloroform at 20℃; for 5h;	100%

Upstream product

• 50-00-0 Formaldehyde 
• 51-17-2 Benzimidazole 
• 1310-58-3 Potassium hydroxide 
• 1317-38-0 Cupric oxide 
• 95-54-5 o-Phenylenediamine 
• 7722-84-1 Hydrogen peroxide 
• 1336-21-6 Ammonium hydroxide 
• 570-22-9 4,5-Imidazoledicarboxylic acid 

Downstream Products

• 10041-02-8 4-(IMIDAZOL-1-YL)PHENOL 
• 23593-75-1 Clotrimazole 
• 65277-42-1 Ketoconazole 
• 93668-43-0 2-Imidazol-1-ylethanamine 
• 27220-47-9 Econazole 
• 65902-59-2 2-Bromo-4-nitroimidazole 
• 68694-11-1 TRIFLUMIZOLE 
• 3034-38-6 4-Nitroimidazole 
• 38083-17-9 Climbazole 
• 10040-98-9 4-(1H-Imidazol-1-yl)benzaldehyde 
• 3034-42-2 1-METHYL-5-NITROIMIDAZOLE 
• 35554-44-0 Imazalil 
• 74204-47-0 1-(1-2-HYDROXYPHENYL)ETHENYL)-1H-IMIDAZOLE 
• 53857-57-1 5-Bromoindazole 
• 368869-85-6 1-[4-(BROMOMETHYL)PHENYL]-1H-PYRAZOLE 
• 69-89-6 2,6-Dihydroxypurine 
• 131747-70-1 2-CYANOPYRIDINE-4-CARBOXALDEHYDE 
• 16042-26-5 1-BENZYL-2-IMIDAZOLECARBOXYLIC ACID 
• 61069-78-1 Sisthsne 
• 71935-32-5 4-(HYDROXYMETHYL)PICOLINITRILE 
• 7164-98-9 1-Phenylimidazole 
• 193269-78-2 1-Boc-3-(Amino)azetidine 
• 64211-46-7 Oxiconazole nitrate 
• 90776-59-3 beta-Methyl vinyl phosphate (MAP) 
• 10111-08-7 Imidazole-2-carboxaldehyde 
• 616-47-7 1-Methylimidazole 
• 22832-87-7 Miconazole nitrate 
• 15965-31-8 4-Chloroimidazole 
• 2574-78-9 Orazamide 
• 2232-08-8 1-[(4-Methylphenyl)sulfonyl]-1H-imidazole 
• 42383-61-9 imidazol-2-ylamine sulphate 
• 5036-48-6 N-(3-Aminopropyl)-imidazole 
• 17616-04-5 4-(1H-IMIDAZOL-1-YL)BENZOIC ACID 
• 159589-67-0 2-(1H-IMIDAZOL-1-YL)BENZOIC ACID 

Recommend Products

• 1615-14-1  1-(2-Hydroxyethyl)imidazole 
• 75-21-8  oxirane 
• 69506-86-1  1,1'-(1,4-butanediyl)bis(imidazole) 
• 110-52-1  1,4-dibromo-butane 
• 4316-42-1  1-Butylimidazole 
• 109-65-9  1-bromo-butane 
• 530-62-1  1,1'-carbonyldiimidazole 
• 75-44-5  phosgene 
• 7098-07-9  N-Ethylimidazole 
• 74-96-4  ethyl bromide 
• 104926-40-1  1H-imidazol-4-yl-N,N-dimethylmethanamine 
• 50-00-0  formaldehyd 
• 506-59-2  N,N-dimethylammonium chloride 
• 93-59-4  Perbenzoic acid