10111-08-7

Basic information

• Product Name: Imidazole-2-carboxaldehyde
• Synonyms: 1H-IMIDAZOLE-2-CARBALDEHYDE;1H-IMIDAZOLE-2-CARBOXALDEHYDE;2-FORMYLIMIDAZOLE;2-IMIDAZOLECARBOXALDEHYDE;IMIDAZOL-2-CARBALDEHYDE;IMIDAZOLE-2-CARBALDEHYDE;IMIDAZOLE-2-CARBOXALDEHYDE;TIMTEC-BB SBB004383
• CAS NO: 10111-08-7
• Molecular Formula: C₄H₄N₂O
• Molecular Weight: 96.09
• EINECS: -0
• Product Categories: Aldehydes;blocks;Imidazoles;Imidazoles & Benzimidazoles;Imidazole;Imidazol&Benzimidazole;Imidaxoles;Imidazoles & Benzimidazoles;Building Blocks;Heterocyclic Building Blocks;Building Blocks;C1 to C6;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks
• Mol File: 10111-08-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 209 °C (dec.)(lit.)
• Boiling Point: 296.5 °C at 760 mmHg
• Flash Point: 137.5 °C
• Appearance: white powder
• Density: 1.322 g/cm³
• Vapor Pressure: 0.00143mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly), Methanol (Slightly, Sonicated)
• PKA: 11.48±0.10(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Air Sensitive
• BRN: 4371302
• CAS DataBase Reference: Imidazole-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Imidazole-2-carboxaldehyde(10111-08-7)
• EPA Substance Registry System: Imidazole-2-carboxaldehyde(10111-08-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39-3
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 10111-08-7(Hazardous Substances Data)

Usage

Chemical Properties

White to light brown solid

Uses

Different sources of media describe the Uses of 10111-08-7 differently. You can refer to the following data:
1. 1H-Imidazole-2-carboxaldehyde is a novel PTP1b inhibitor with potential application to treat type 2 diabetes.
2. Used in a study of the imidazole-directed allylation of aldimines.1
3. Imidazole-2-carboxaldehyde is a novel protein tyrosine phosphatase 1B (PTP1B) inhibitor with an important application to treat type-2 diabetes. It is used in the preparation of tridentate Schiff-base carboxylate-containing ligands by undergoing condensation reaction with amino acids beta-alanine and 2-aminobenzoic acid. It is also involved in the study of the imidazole-directed allylation of aldimines.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 287, 1990The Journal of Organic Chemistry, 60, p. 1090, 1995 DOI: 10.1021/jo00109a052

InChI:InChI=1/C4H4N2O/c7-3-4-5-1-2-6-4/h1-3H,(H,5,6)

Upstream product

• 16681-56-4 2-bromo-1H-imidazole 
• 68-12-2 N,N-dimethyl-formamide 
• 1582276-25-2 C₁₈H₁₆N₄ 
• 65276-01-9 2-(1,3-dibenzoylimidazolidin-2-yl)imidazole hydrochloride 
• 107-31-3 Methyl formate 
• 91272-86-5 N-((1H-imidazol-1-yl)methyl)-N-ethylethanamine 
• 67478-50-6 1-(triphenylmethyl)-1H-imidazole-2-carboxaldehyde 
• 78667-05-7 N-((1H-imidazol-5-yl)methoxy)phthalimide 

Downstream Products

• 51789-99-2 pyrrolo<1,2-a>imidazol-5-one 
• 95460-12-1 1-(4-methoxybenzyl)-1H-imidazole-2-carbaldehyde 
• 660405-09-4 4-trifluoromethylphenyl-1H-imidazol-2-ylmethylamine 
• 660405-07-2 4-trifluoromethoxyphenyl-1H-imidazol-2-ylmethylamine 
• 660405-12-9 4-bromophenyl-1H-imidazol-2-ylmethylamine 
• 497855-75-1 1-cyclopropylmethylimidazole-2-carboxyaldehyde 
• 10045-65-5 N-benzylimidazole-2-carboxaldehyde 
• 702690-15-1 (S,S)-6-{4-[(1H-imidazol-2-ylmethyl)-amino]-butyl}-3-(4-methoxy-benzyl)-1-(4-phenoxy-benzyl)-piperazine-2,5-dione 
• 396091-04-6 3-(1-methylindol-3-yl)-4-[3-(imidazol-2-ylmethylamino)phenyl]-1H-pyrrole-2,5-dione 
• 509090-93-1 C₁₂H₁₃N₃O₂ 
• 927885-52-7 {(4-dipropylaminobutyl)-[4-(1H-imidazol-2-ylmethylidene)aminomethylbenzyl]}-methyl-amine 
• 927885-46-9 {(4-dipropylaminobutyl)-[4-(1H-imidazole-2-ylmethylidene)aminomethylbenzyl]amino}acetic acid ethyl ester 

Relevant articles and documents

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Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N- (ω-bromoalkyl) or N-[ω-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regio-selective radical cyclisalion onto the azole rings followed by oxidative re-aromatisation.

Improved synthesis of imidazole-2-carboxaldehyde, imidazole-2-carboxylic acid, and ethyl imidazole-2-carboxylate

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Asymmetric Copper(II)-catalysed nitroaldol (Henry) reactions utilizing a chiral C1-symmetric dinitrogen ligand

A series of stable chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(-)-exo-bornylamine or (+)-(1S,2S,5R)-menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 in combination with CuCl2·2H2O (2.5 mol-% or 5.0 mol-%) can efficiently promote nitroaldol (Henry) reactions between a variety of aldehydes and nitromethane. Both aromatic and aliphatic aldehydes were tolerated in our catalytic system, affording the expected nitroalcohol products in high yields (up to 97%) and with good enantioselectivities (up to 96%) under mild reaction conditions. A series of chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensations of chiralamines with various substituted imidazolecarbaldehydes. The ligand L1 in conjunction with CuCl2·2H2O can efficiently promote nitroaldol (Henry) reactions between various aldehydes and nitromethane in high yields (up to 97%) and with good enantioselectivities (up to 96%).