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Imidazole

Product Name
Imidazole
CAS No.
288-32-4
Chemical Name
Imidazole
Synonyms
1H-IMIDAZOLE;Imidazol;IMZ;IMD;GLYOXALINE;LMIDAZOLE;GLYOXALIN;IMINAZOLE;Imidazoie;1H-Imidazol
CBNumber
CB6460617
Molecular Formula
C3H4N2
Formula Weight
68.08
MOL File
288-32-4.mol
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Imidazole Property

Melting point:
88-91 °C(lit.)
Boiling point:
256 °C(lit.)
Density 
1.01 g/mL at 20 °C
vapor pressure 
<1 mm Hg ( 20 °C)
refractive index 
1.4801
Flash point:
293 °F
storage temp. 
Store below +30°C.
solubility 
H2O: 0.1 M at 20 °C, clear, colorless
pka
6.953(at 25℃)
form 
crystalline
color 
white
Specific Gravity
1.03
Odor
Amine like
PH Range
9.5 - 11
PH
9.5-11.0 (25℃, 50mg/mL in H2O)
Water Solubility 
633 g/L (20 ºC)
Sensitive 
Hygroscopic
λmax
λ: 260 nm Amax: 0.10
λ: 280 nm Amax: 0.10
Merck 
14,4912
BRN 
103853
Dielectric constant
23.0（Ambient）
Stability:
Stable. Incompatible with acids, strong oxidizing agents. Protect from moisture.
InChIKey
RAXXELZNTBOGNW-UHFFFAOYSA-N
LogP
-0.02 at 25℃
CAS DataBase Reference
288-32-4(CAS DataBase Reference)
NIST Chemistry Reference
1H-Imidazole(288-32-4)
EPA Substance Registry System
Imidazole (288-32-4)
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Safety

Hazard Codes 
C,Xi,T
Risk 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
Autoignition Temperature
480 °C
TSCA 
Yes
HazardClass 
8
PackingGroup 
III
HS Code 
29332990
Hazardous Substances Data
288-32-4(Hazardous Substances Data)
Toxicity
LD50 in mice (mg/kg): 610 i.p.; 1880 orally (Nishie)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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
RDD044
Product name
Imidazole
Purity
ReagentPlus?, 99%, Redi-Dri?, free-flowing
Packaging
100G
Price
$48.8
Updated
2024/03/01
Sigma-Aldrich
Product number
RDD044
Product name
Imidazole
Purity
ReagentPlus?, 99%, Redi-Dri?, free-flowing
Packaging
500G
Price
$148
Updated
2024/03/01
Sigma-Aldrich
Product number
RDD044
Product name
Imidazole
Purity
ReagentPlus?, 99%, Redi-Dri?, free-flowing
Packaging
1KG
Price
$262
Updated
2024/03/01
Sigma-Aldrich
Product number
RDD044
Product name
Imidazole
Purity
ReagentPlus?, 99%, Redi-Dri?, free-flowing
Packaging
2.5KG
Price
$446
Updated
2024/03/01
Sigma-Aldrich
Product number
RDD039
Product name
Imidazole
Purity
for molecular biology, ≥99% (titration), free-flowing, Redi-Dri?
Packaging
100G
Price
$721
Updated
2024/03/01
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Imidazole Chemical Properties,Usage,Production

Description

Imidazole group denotes a heterocyclic organic compound whose molecule contains a five-membered hetero-aromatic ring of two non-adjacent nitrogen atoms, that a carbon atom is placed between two nitrogen atoms. Imidazole is the universally used trivial name for 1,3-azole. Earlier given names were glyoxaline and iminazole. The importance of this aromatic ring system is reflected by its presence in naturally occurring histidine, histamine and the purines, and in several classes of pharmaceuticals. Imidazole can act as a base and as a weak acid. It exists in two tautomeric forms with the hydrogen atom taking position between the two nitrogen atoms.

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. It is an important pharmacophore in drug discovery. Imidazole is used as a Karl Fischer reagent in analytical chemistry and a reagent in synthetic organic chemistry.

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.

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).

Mechanism of action

N-substitution of imidazoles has created a family of drugs, called triazoles, that have the same mechanism of action as imidazoles, a similar or broader spectrum of activity, and less effect on human sterol synthesis. Both imidazoles and triazoles inhibit C-14α demethylation of lanosterol in fungi by binding to one of the cytochrome P-450 enzymes, which leads to the accumulation of C-14α methylsterols and reduced concentrations of ergosterol, a sterol essential for a normal fungal cytoplasmic membrane. Inhibition of cytochrome P-450 also decreases the synthesis of testosterone and glucocorticoids in mammals, an effect seen clinically with ketoconazole but not with later azoles[1].

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.]

References

[1] Rex, J. and D. Stevens. “39 – Drugs Active against Fungi, Pneumocystis, and Microsporidia.” Mandell, Douglas, and Bennett’s Principles and Practice of Infectious Diseases 23 1 (2015): 479-494.

Imidazole Preparation Products And Raw materials

Raw materials

4,5-Imidazoledicarboxylic acid Glyoxal Ammonium hydroxide Benzimidazole Potassium hydroxide Hydrogen peroxide Formaldehyde Cupric oxide Concentrated sulfuric acid Ammonium chloride Hydrochloric acid Benzimidazole o-Phenylenediamine

Preparation Products

2-(1H-IMIDAZOL-1-YL)BENZOIC ACID Xanthine Imidazole-2-carboxaldehyde beta-Methyl vinyl phosphate (MAP) Miconazole nitrate 2-Bromo-4-nitroimidazole imidazol-2-ylamine sulphate 1-Methylimidazole 4-(IMIDAZOL-1-YL)PHENOL Orazamide 6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBONITRILE 1-(1-2-HYDROXYPHENYL)ETHENYL)-1H-IMIDAZOLE 1-Boc-3-(Amino)azetidine 1-[4-(BROMOMETHYL)PHENYL]-1H-PYRAZOLE 5-bromo-1H-indazole N-(3-Aminopropyl)-imidazole 4-Chloroimidazole 1-Phenylimidazole TRIFLUMIZOLE 1-[(4-Methylphenyl)sulfonyl]-1H-imidazole 6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACID Imazalil Oxiconazole nitrate 1-BENZYL-2-IMIDAZOLECARBOXYLIC ACID 2-CYANOPYRIDINE-4-CARBOXALDEHYDE 4-(1H-IMIDAZOL-1-YL)BENZOIC ACID Clotrimazole Detergent,industrial chloroalcohol type homogeneous strongly basic anion exchange membrane 4-(HYDROXYMETHYL)PICOLINITRILE (S)-4-BOC-MORPHOLINE-3-CARBOXYLIC ACID 1-METHYL-5-NITROIMIDAZOLE Climbazole 4-(1H-Imidazol-1-yl)benzaldehyde 4-Nitroimidazole Sisthsne Ketoconazole 2-Imidazol-1-ylethanamine Econazole 5-(AMINOMETHYL)-1-METHYLPYRROLIDIN-2-ONE
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Imidazole Suppliers

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View Lastest Price from Imidazole manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Dihydrate Zinc Acetate 288-32-4
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-24
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Imidazole 288-32-4
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-24
Ningxia Jinhua Chemical Co.,Ltd
Product
Imidazole 288-32-4
Price
US $6000.00/kg
Min. Order
1000kg
Purity
99%
Supply Ability
500 tons
Release date
2023-12-14

288-32-4, ImidazoleRelated Search:

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  • 1H-IMIDAZOLE
  • 1,3-DIAZA-2,4-CYCLOPENTADIENE
  • 1,3-DIAZOLE
  • LABOTEST-BB LTBB001344
  • IMIDAZOLE BUFFER
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  • N,N'-VINYLENEFORMAMIDINE
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  • Imidazole, 99+%, crystalline
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  • 1,3-Diaza-2,4-cyclopentadiene, high purity >99%
  • Imidazole high purity
  • Imidazole Zone Refined (number of passes:30)
  • Imidazole [for Buffer]
  • Imidazole [for Fluorimetric Analysis]
  • Glyoxaline, lminazole
  • IMIDAZOLE extrapure AR
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  • Imidazole,1,3-Diaza-2,4-cyclopentadiene, Glyoxaline
  • Ondansetron impurity E (Ph Eur)
  • Ondansetron impurity E
  • IMidazole 0.25
  • Crystallization solution 6/Fluka-Kit No 70437
  • Ondansetron EP Impurity E
  • Imidazole anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99%
  • Imidazole Vetec(TM) reagent grade, 98%
  • R2 BROTH 2.5ML X 50 TUBES
  • SAFRANIN O CERTIFIABLE GRADE
  • SILICA GEL CHAMELEON C 1-3 MM
  • SILICA GEL CHAMELEON C 2-6 MM
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  • Imidazole, 99.5%, BioUltra
  • Ozagrel Impurity 25
  • Clotrimazole Impurity 4(Clotrimazole EP Impurity D)