Imidazole

Base Information

• Chemical Name: Imidazole
• CAS No.: 288-32-4
• Deprecated CAS: 116421-26-2,146117-15-9,146117-15-9
• Molecular Formula: C3H4N2
• Molecular Weight: 68.0782
• Hs Code.: 29332990
• European Community (EC) Number: 206-019-2
• ICSC Number: 1721
• NSC Number: 60522
• UN Number: 3263
• UNII: 7GBN705NH1
• DSSTox Substance ID: DTXSID2029616
• Nikkaji Number: J2.059.038F,J2.566F
• Wikipedia: Imidazole
• Wikidata: Q328692
• Metabolomics Workbench ID: 37848
• ChEMBL ID: CHEMBL540
• Mol file: 288-32-4.mol

Synonyms:Methanimidamide, N,N-1,2-ethenediyl-;1H-Imidazole (9CI);1H-Imidazole, monohydrochloride;1,3-Diazole;1,3-Diaza-2,4-cyclopentadiene;Imidazol;Methanimidamide, N,N-1, 2-ethenediyl-;Formamidine, N,N-vinylene-;Him;IMD;Glyoxaline;1467-16-9;Glyoxalin;Iminazole;Imutex;imidazole chloride;Pyrro(b)monazole;Miazole;2-phenyl-4,5-dihydroxy metylimidazole;

Chemical Property of Imidazole

Chemical Property:

• Appearance/Colour: white to off white crystals
• Vapor Pressure: <1 mm Hg ( 20 °C)
• Melting Point: 88-91 °C(lit.)
• Refractive Index: 1.4801
• Boiling Point: 257 °C at 760 mmHg
• PKA: 6.953(at 25℃)
• Flash Point: 145 °C
• PSA: 28.68000
• Density: 1.116 g/cm³
• LogP: 0.40970
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 M at 20 °C, clear, colorless
• Water Solubility.: 633 g/L (20 ºC)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 68.037448136
• Heavy Atom Count: 5
• Complexity: 28.1

Purity/Quality:

99.0% ^*data from raw suppliers

Imidazole, 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Imidazoles
• Canonical SMILES: C1=CN=CN1
• Recent NIPH Clinical Trials: Validation study of the anti-fatigue effects of imidazole dipeptide for the person performing daily exercise
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the skin. The substance is severely irritating to the eyes. The substance is irritating to the respiratory tract.
• Effects of Long Term Exposure: Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• Chemical Structure: Imidazole is an aromatic diazole and alkaloid with anticancer properties. It is a planar five-member heterocyclic ring with 3 carbon (C) and 2 nitrogen (N) atoms, where nitrogen is present in the 1st and 3rd positions. It exists in two equivalent tautomeric forms due to the hydrogen atom being able to be located on either of the two nitrogen atoms.
• Properties: Imidazole is soluble in water and other polar solvents. It is highly polar with a calculated dipole of 3.61D.; Imidazole is classified as aromatic due to the presence of a sextet of π-electrons.; It is amphoteric, functioning both as an acid and as a base.; The pKa of imidazole as an acid is 14.5, while as a base, the pKa of the conjugate acid is approximately 7.
• Pharmacological Activities: Imidazole derivatives exhibit various pharmacological activities such as anti-fungal, anti-bacterial, anti-inflammatory, analgesic, anti-tubercular, anti-depressant, anti-viral, and antileishmanial activities.
• Historical Background: Imidazole was first synthesized in 1858 by Heinrich Debus. The name "imidazole" was coined in 1887 by the German chemist Arthur Rudolf Hantzsch.
• Industrial and Technological Applications: Imidazole is present in many important biological molecules such as histidine, histamine, and nucleic acids. It plays a vital part in the structure and binding functions of proteins and enzymes. Imidazole is used in the purification of His-tagged proteins in immobilized metal affinity chromatography (IMAC). Synthetic imidazoles are used in pharmaceuticals, including fungicides, antifungal, antiprotozoal, and antihypertensive medications.; Imidazole is used as a corrosion inhibitor on certain transition metals like copper. It is present in thermostable polybenzimidazole (PBI), acting as a fire retardant. Various compounds containing imidazole derivatives are used in photography and electronics.

Technology Process of Imidazole

There total 295 articles about Imidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

Glyoxal (131543-46-9,107-22-2) + isobutyraldehyde (78-84-2) → 1H-imidazole (288-32-4) + 2-isopropylimidazole (36947-68-9)

Guidance literature:

isobutyraldehyde; With ammonia; In methanol; water; at 25 ℃; for 1h;

Glyoxal; With ammonia; In methanol; water; at 25 ℃; for 2h; Product distribution / selectivity;

Reference yield: 94.0%

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)

Guidance literature:

In diethyl ether; for 0.166667h; Ambient temperature;

Reference yield: 60.0%

→ 1H-imidazole (288-32-4) + DL-methionine (59-51-8,26062-47-5,58576-49-1)

Guidance literature:

upstream raw materials:

N-Acetylimidazole

formaldehyd

glyoxal sulfate

N-phenyl-1H-imidazole-1-carboxamide

Downstream raw materials:

2-(imidazol-1-yl-diphenyl-methyl)-thiazole

2-(1-chloro-9-phenyl-xanthen-9-yl)-1H-imidazole

1-Chlor-9-(imidazo-1-yl)-9-phenylxanthin

4-(1⁽³⁾H-imidazol-4-ylmethylene)-2-phenyl-4H-oxazol-5-one

Refernces

• 1、 Slightom, J. L.,Bolen, D. W.. "Enthalpy Changes Accompanying Hydrolysis of 3-(2-Furyl)acryloylimidazole by α-Chymotrypsin". . p. 6318 - 6324. Retrieved 1980.
• 2、 Gridnev,Mihaltseva. "Synthesis of 1-alkylimidazoles". . p. 1547 - 1555. Retrieved 1994.
• 3、 Di Fabio, Giovanni,Libralato, Giovanni,Luongo, Giovanni,Previtera, Lucio,Saviano, Lorenzo,Serafini, Sara,Siciliano, Antonietta,Zarrelli, Armando. "Lc and nmr studies for identification and characterization of degradation byproducts of olmesartan acid, elucidation of their degradation pathway and ecotoxicity assessment". . . Retrieved 2021.
• 4、 Caldin, Edward,Field, John P.. "KINETICS OF FORMATION OF THE ELECTON DONOR-ACCEPTOR COMPLEX BETWEEN IODINE AND IMIDAZOLE IN CHLOROBUTANE SOLUTION". . p. 1937 - 1942. Retrieved 1982.
• 5、 McClelland, Robert A.. "Rate-Limiting Deprotonation in Tetrahedral Intermediate Breakdown". . p. 7579 - 7583. Retrieved 1984.
• 6、 Neverov,Montoya-Pelaez,Brown. "Catalysis of the methanolysis of activated amides by divalent and trivalent metal ions. The effect of Zn2+, Co2+, and La3+ on the methanolysis of acetylimidazole and its (NH3)5CoIII complex". . p. 210 - 217. Retrieved 2001.
• 7、 Li, Lili,Yang, Linlin,Li, Xuezhao,Wang, Jing,Liu, Xin,He, Cheng. "Supramolecular Catalysis of Acyl Transfer within Zinc Porphyrin-Based Metal-Organic Cages". supporting information. p. 8802 - 8810. Retrieved 2021/06/28.