68282-53-1

Basic information

• Product Name: 5-Methyl-1H-imidazole-4-carbaldehyde
• Synonyms: 5-Formyl-4-methyl-1H-imidazole;4-Methyl-5-iMidazolecarboxaldehyde 99%;392154_ALDRICH;5-methyl-1H-imidazole-4-carboxaldehyde;SB 01366;ZINC00164641;4-Methyl-1H-imidazol-5-carbaldehyde;5-METHYLIMIDAZOLE-4-CARBOXALDEHYDE
• CAS NO: 68282-53-1
• Molecular Formula: C₅H₆N₂O
• Molecular Weight: 110.11
• Product Categories: Building Blocks;C1 to C6;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks;ALDEHYDE;pharmacetical;Aldehydes;Imidazoles & Benzimidazoles;Heterocyclic Compounds;Imidazoles & Benzimidazoles;Building Blocks;Heterocyclic Building Blocks;Imidazoles
• Mol File: 68282-53-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 168-170 °C(lit.)
• Boiling Point: 362.8oC at 760 mmHg
• Flash Point: 176.9oC
• Appearance: /
• Density: 1.238g/cm3
• Vapor Pressure: 1.89E-05mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 11.48±0.10(Predicted)
• Water Solubility: Soluble in water, (23 g/L) (25°C).
• Sensitive: Air Sensitive
• CAS DataBase Reference: 5-Methyl-1H-imidazole-4-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-1H-imidazole-4-carbaldehyde(68282-53-1)
• EPA Substance Registry System: 5-Methyl-1H-imidazole-4-carbaldehyde(68282-53-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 68282-53-1(Hazardous Substances Data)

Usage

Uses

4-Methyl-5-imidazolecarboxaldehyde is suitable for use in the synthesis of the following:1,3-bis[(4-methyl-5-imidazol-1-yl)ethylideneamino]-propan-2-ol (BIPO).1,3-bis[(4-methyl-5-imidazol-1-yl)ethylideneamino]propane (BIP).{acetatoaqua[[(4-methylimidazol-5-yl)methylene]histamine]-copper(II)} perchlorate.Schiff base condensates with tris(2-aminoethyl)amine (tren) or tris(3-aminopropyl)amine (trpn).It may be used in the synthesis of the following:Imidazolate-based metal organic framework (MOF) membrane.3,11-bis(4-imidazolylmethyl)-7-methyl-3,7,11,17-tetraazabicyclo[11.3.1]hepta-deca-1(17),13,15-triene, a 4-imidazolyl derivative of a 14-membered tetraazamacrocycle.Cu(II) eight and six coordinate compounds.

General Description

4-Methyl-5-imidazolecarboxaldehyde is an imidazole carboxaldehyde.

InChI:InChI=1/C5H6N2O/c1-4-5(2-8)7-3-6-4/h2-3H,1H3,(H,6,7)

Upstream product

• 29636-87-1 4⁽⁵⁾-methyl-5⁽⁴⁾-hydroxymethylimidazole 
• 29636-87-1 4-methyl-5-hydroxymethylimidazole 
• 108512-05-6 N-(3-methyl-4-isoxazolyl)formamide 

Downstream Products

• 75815-57-5 5-methyl-1-(phenylmethyl)-1H-imidazole-4-carboxaldehyde 
• 850788-95-3 2,4-di-tert-butyl-6-[(5-methyl-3H-imidazol-4-ylmethyl)amino]phenol 
• 1164117-94-5 N-[(5-methylimidazol-4-yl)methylidene]-DL-phenylalanine 
• 87471-66-7 4-[N-(3',5'-dichlorophenyl)-iminomethyl]-5-methylimidazole 
• 1201677-77-1 C₂₅H₃₂N₄O₂S 
• 1185190-85-5 C₂₀H₂₀IN₃O₂S 
• 1185190-83-3 3-[4-(3,5-dimethylphenylsulfanyl)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylmethyl]-5-methyl-3H-imidazol-4-ylcarbaldehyde 
• 1428943-79-6 N-(tert-butyl)-8-(4-methoxybenzyl)-1,5-dimethyl-7-oxo-8,9-dihydro-7H-imidazo[1,5-a][1,4]diazepine-9-carboxamide 
• 1428943-61-6 N-(2-(tert-butylamino)-1-(5-methyl-1H-imidazol-4-yl)-2-oxoethyl)-N-(4-methoxybenzyl)but-2-ynamide 
• 1428943-70-7 N-cyclohexyl-8-(4-methoxybenzyl)-1,5-dimethyl-7-oxo-8,9-dihydro-7H-imidazo[1,5-a][1,4]diazepine-9-carboxamide 
• 1428943-52-5 N-(2-(cyclohexylamino)-1-(5-methyl-1H-imidazol-4-yl)-2-oxoethyl)-N-(4-methoxybenzyl)but-2-ynamide 
• 1428943-76-3 N-cyclohexyl-8-(3,4-dimethoxybenzyl)-1,5-dimethyl-7-oxo-8,9-dihydro-7H-imidazo[1,5-a][1,4]diazepine-9-carboxamide 
• 1428943-58-1 N-(2-(cyclohexylamino)-1-(5-methyl-1H-imidazol-4-yl)-2-oxoethyl)-N-(3,4-dimethoxybenzyl)but-2-ynamide 
• 1437869-62-9 1-(4-methylimidazol-5-yl)(phenylhydrazono)propane-2-one oxime 

Relevant articles and documents

Design and synthesis of novel potent antinociceptive agents: Methyl-imidazolyl N-acylhydrazone derivatives

This paper describes recent results of design, synthesis and pharmacological evaluation of new N-heterocyclic functionalized N-acylhydrazone compounds, belonging to the 2-methyl-imidazolyl-3-acylhydrazone class (4a-e). These compounds were planned by applying the molecular simplification strategy to propose the structural modifications on the previously described functionalized imidazo[1,2-a]pyridine 3-acylhydrazone series (2), which presented an important analgesic profile. This new series (4) was synthesized in order to investigate the possible pharmacophoric contribution of the N-heteroaromatic ring and N-acylhydrazone moieties to the analgesic activity. Compounds 4a-b are the most potent antinociceptive agents from this series. Copyright (C) 2000 Elsevier Science Ltd.

Synthesis of 4(5)-Acyl-, 1-Substituted 5-Acyl, and 1-Substituted 4-Acyl-1H-imidazoles from 4-Aminoisoxazoles

4-Aminoisoxazoles can be acylated with a wide variety of activated carboxylic acids.Hydrogenation of the resulting amides gives α-(acylamino)enaminones, which cyclize to 4(5)-acylimidazoles upon treatment with base.This method allows for the synthesis of acylimidazoles with a wide range of substituents at C-2.Utilization of N-substituted 4-aminoisoxazoles in the same sequence of reactions yields 1-substituted 5-acylimidazoles, a substitution pattern not otherwise easily prepared.Treatment of α-(acylamino)enaminones, derived from N-unsubstituted isoxazoles, with primary amines leads to incorporation of the amine at the β-position with concomitant expulsion of ammonia.This sequence efficiently yields 1-substituted and 1,2-disubstituted 4-acylimidazoles but does not give satisfactory yields of 5-substituted 4-acylimidazoles due to steric inhibition of the amine exchange.