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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
Molecular Weight:
68.08
MDL Number:
MFCD00005183
MOL File:
288-32-4.mol
MSDS File:
SDS
Modify Date:2023-03-17 14:11:50

Imidazole Properties

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
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)
EWG's Food Scores 1
FDA UNII 7GBN705NH1
NIST Chemistry Reference 1H-Imidazole(288-32-4)
EPA Substance Registry System Imidazole (288-32-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H314-H360D
Precautionary statements  P260-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
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
Toxicity LD50 in mice (mg/kg): 610 i.p.; 1880 orally (Nishie)
NFPA 704
1
3 0

Imidazole price More Price(143)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich RDD044 Imidazole ReagentPlus?, 99%, Redi-Dri?, free-flowing 288-32-4 100G $46.9 2023-01-07 Buy
Sigma-Aldrich RDD044 Imidazole ReagentPlus?, 99%, Redi-Dri?, free-flowing 288-32-4 500G $142 2023-01-07 Buy
Sigma-Aldrich RDD044 Imidazole ReagentPlus?, 99%, Redi-Dri?, free-flowing 288-32-4 1KG $252 2023-01-07 Buy
Sigma-Aldrich RDD044 Imidazole ReagentPlus?, 99%, Redi-Dri?, free-flowing 288-32-4 2.5KG $429 2023-01-07 Buy
Sigma-Aldrich RDD039 Imidazole for molecular biology, ≥99% (titration), free-flowing, Redi-Dri? 288-32-4 100G $693 2023-01-07 Buy
Product number Packaging Price Buy
RDD044 100G $46.9 Buy
RDD044 500G $142 Buy
RDD044 1KG $252 Buy
RDD044 2.5KG $429 Buy
RDD039 100G $693 Buy

Imidazole Chemical Properties,Uses,Production

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.
synthesis of Imidazole
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).

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.]

Imidazole Suppliers

Global( 1040)Suppliers
Supplier Tel Email Country ProdList Advantage
Nanjing MSN chemical Co., Ltd
25-57015632 +8618913029712 export@msnchem.com China 25 34
Anhui Royal Chemical Co., Ltd.
+86-25-86655873 +8613962173137 marketing@royal-chem.com China 535 55
Shandong Believe Chemical PTE.LTD
+8618553607090 1093908296@qq.com China 1750 58
Hebei Crovell Biotech Co Ltd
+86-19930503285 zoey@crovellbio.com China 3930 58
Hefei TNJ Chemical Industry Co.,Ltd.
0551-65418671 sales@tnjchem.com CHINA 34572 58
Jiangsu Guotai Guomian Trading Co. Ltd.
+86-512-58916079 +86-13601562190 pharmachem@gtgmt.com China 148 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806 sales@capotchem.com China 29810 60
Henan DaKen Chemical CO.,LTD.
+86-371-66670886 info@dakenchem.com China 17713 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21975 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555 +8617317452075 jack.li@time-chemicals.com China 1807 55

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View Lastest Price from Imidazole manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Imidazole pictures 2023-03-29 Imidazole
288-32-4
US $5.00 / kg 10kg 99% 20tons Hebei Linwo New Material Technology Co., LTD
Imidazole pictures 2023-03-28 Imidazole
288-32-4
US $0.00 / KG 1KG 99% 1000mt/year Jinan Finer Chemical Co., Ltd
Imidazole pictures 2023-03-27 Imidazole
288-32-4
US $50.00 / KG 1KG 0.99 20t XINGTAI XINGJIU NEW MATERIAL TECHNOLOGY CO., LTD
  • Imidazole pictures
  • Imidazole
    288-32-4
  • US $5.00 / kg
  • 99%
  • Hebei Linwo New Material Technology Co., LTD
  • Imidazole pictures
  • Imidazole
    288-32-4
  • US $0.00 / KG
  • 99%
  • Jinan Finer Chemical Co., Ltd
  • Imidazole pictures
  • Imidazole
    288-32-4
  • US $50.00 / KG
  • 0.99
  • XINGTAI XINGJIU NEW MATERIAL TECHNOLOGY CO., LTD
1H-IMIDAZOLE 1,3-DIAZA-2,4-CYCLOPENTADIENE 1,3-DIAZOLE LABOTEST-BB LTBB001344 IMIDAZOLE BUFFER IMINAZOLE IMIDAZOLE GLYOXALIN GLYOXALINE GLYOXALINE BUFFER N,N'-VINYLENEFORMAMIDINE AKOS BBS-00004265 imidazole buffer solution IMIDAZOLE,REAGENT Imidazoie LMIDAZOLE Imidazole Zone Refined Glyoxaline solution, Imidazole solution 1,3-Diaza-2,4-cyclopentadiene, Glyoxaline Imidazole, 99+%, crystalline Imidazole, crystalline Imidazole,for analysis ACS IMIDAZOLE BUFFER GRADE IMIDAZOLE MOLECULAR BIOLOGY GRADE 1,3-DIAZA-2,4-CYCLOPENTADIENE, HIGH PURITY 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 IMIDAZOLE pure IMIDAZOLEANALYTICAL GRADE IMIDAZOLERESEARCH GRADE 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 SODIUM PHOSPHATE MONOBASIC ANHYD REAGENT Imidazole for Fluorometric Imidazole≥ 99% (GC) FINE ORGANIC COMPOUND , IMIDAZOLE DERIVA 1,3-Diazole Glyoxaline 1,3-diaza-2,4-cyclopentadiene n,n'-vinylene-formamidin Imidazole, ULTROL Bifonazole EP Impurity C IMIDAZOLE BUFFER SOLUTION, 1M IN Imidazole, 99.5%, BioUltra Ozagrel Impurity 25 Clotrimazole Impurity 4(Clotrimazole EP Impurity D)