Home Imidazoles 822-36-6
822-36-6,MFCD01074774
Catalog No.:AA00340U

822-36-6 | 4-Methylimidazole

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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA00340U
Chemical Name:
4-Methylimidazole
CAS Number:
822-36-6
Molecular Formula:
C4H6N2
Molecular Weight:
82.1038
MDL Number:
MFCD01074774
SMILES:
Cc1c[nH]cn1
NSC Number:
40744
Properties
Properties
 
BP:
263.0°C  
Form:
Solid  
MP:
44-47 °C(lit.)  
Refractive Index:
1.5037  
Solubility:
H2O: soluble, clear, colorless to yellow (50 mg/mL)  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
44.8  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
6  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
XLogP3:
0.2  

Literature

Title: Switching orientation of two axial imidazole ligands between parallel and perpendicular in low-spin Fe(III) and Fe(II) nonplanar porphyrinates.

Journal: Inorganic chemistry 20121105

Title: Comparative risk assessment of carcinogens in alcoholic beverages using the margin of exposure approach.

Journal: International journal of cancer 20120915

Title: Re-evaluation of the proton affinity of 18-crown-6 using competitive threshold collision-induced dissociation techniques.

Journal: Analytical chemistry 20120904

Title: Accurate structure and dynamics of the metal-site of paramagnetic metalloproteins from NMR parameters using natural bond orbitals.

Journal: Journal of the American Chemical Society 20120314

Title: Self-assembly of the oxy-tyrosinase core and the fundamental components of phenolic hydroxylation.

Journal: Nature chemistry 20120304

Title: Simultaneous quantitation of 2-acetyl-4-tetrahydroxybutylimidazole, 2- and 4-methylimidazoles, and 5-hydroxymethylfurfural in beverages by ultrahigh-performance liquid chromatography-tandem mass spectrometry.

Journal: Journal of agricultural and food chemistry 20120201

Title: Structural and energetic effects in the molecular recognition of protonated peptidomimetic bases by 18-crown-6.

Journal: Journal of the American Chemical Society 20120201

Title: Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: application to the synthesis of nilotinib.

Journal: Journal of the American Chemical Society 20120111

Title: Determination of 4(5)-methylimidazole in soy sauce and other foods by LC-MS/MS after solid-phase extraction.

Journal: Journal of agricultural and food chemistry 20110928

Title: Reengineering rate-limiting, millisecond enzyme motions by introduction of an unnatural amino acid.

Journal: Biophysical journal 20110720

Title: Quantification of 4-methylimidazole in class III and IV caramel colors: validation of a new method based on heart-cutting two-dimensional liquid chromatography (LC-LC).

Journal: Journal of agricultural and food chemistry 20110427

Title: Chemical rescue of enzymes: proton transfer in mutants of human carbonic anhydrase II.

Journal: Journal of the American Chemical Society 20110427

Title: Structure of rhomboid protease in a lipid environment.

Journal: Journal of molecular biology 20110325

Title: Protonation, tautomerization, and rotameric structure of histidine: a comprehensive study by magic-angle-spinning solid-state NMR.

Journal: Journal of the American Chemical Society 20110209

Title: Formation of carcinogenic 4(5)-methylimidazole in Maillard reaction systems.

Journal: Journal of agricultural and food chemistry 20110126

Title: Does 4-methylimidazole have tumor preventive activity in the rat?

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110101

Title: Conformationally constrained histidines in the design of peptidomimetics: strategies for the χ-space control.

Journal: International journal of molecular sciences 20110101

Title: Structural studies of β-carbonic anhydrase from the green alga Coccomyxa: inhibitor complexes with anions and acetazolamide.

Journal: PloS one 20110101

Title: A comparative structural bioinformatics analysis of inherited mutations in β-D-Mannosidase across multiple species reveals a genotype-phenotype correlation.

Journal: BMC genomics 20110101

Title: Ligand effects on the [Cu(PhO)(PhOH)]+ redox active complex.

Journal: Inorganic chemistry 20100920

Title: A model study of the efficiency of the Asp-His-Ser triad.

Journal: Journal of computational chemistry 20100715

Title: Structural and mechanistic insights into the oxy form of tyrosinase from molecular dynamics simulations.

Journal: Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20100201

Title: Two two-dimensional hydrogen-bonded coordination networks: bis(3-carboxybenzoato-kappaO)bis(4-methyl-1H-imidazole-kappaN3)copper(II) and bis(3-methylbenzoato-kappaN)bis(4-methyl-1H-imidazole-kappaN3)copper(II) monohydrate.

Journal: Acta crystallographica. Section C, Crystal structure communications 20091201

Title: DFT calculations of the EPR parameters for Cu(ii) DETA imidazole complexes.

Journal: Physical chemistry chemical physics : PCCP 20091001

Title: Three-dimensional networks in bis(imidazolium) 2,2'-dithiodibenzoate and 4-methylimidazolium 2-[(2-carboxyphenyl)disulfanyl]benzoate.

Journal: Acta crystallographica. Section C, Crystal structure communications 20090901

Title: Histidine side-chain dynamics and protonation monitored by 13C CPMG NMR relaxation dispersion.

Journal: Journal of biomolecular NMR 20090801

Title: Light-induced oxidation of tryptophan and histidine. Reactivity of aromatic N-heterocycles toward triplet-excited flavins.

Journal: Journal of the American Chemical Society 20090617

Title: Microfluidic device capable of sensing ultrafast chemiluminescence.

Journal: Talanta 20090515

Title: Comparative analysis of mutant tyrosine kinase chemical rescue.

Journal: Biochemistry 20090421

Title: Effects of 4-methylimidazole on cerebral glutamate decarboxylase activity and specific GABA receptor binding in mice.

Journal: Toxicology mechanisms and methods 20090301

Title: Bis(4-methyl-imidazolium) succinate succinic acid solvate.

Journal: Acta crystallographica. Section E, Structure reports online 20090301

Title: A DFT study of the 67Zn, 14N and 2H electric field gradient tensors in Zinc(II)-4-MeIm complexes and extrapolation to superoxide dismutase.

Journal: Journal of molecular graphics & modelling 20090101

Title: Structures of human cytochrome P-450 2E1. Insights into the binding of inhibitors and both small molecular weight and fatty acid substrates.

Journal: The Journal of biological chemistry 20081128

Title: Reaction dynamics of excited 2-(3-benzoylphenyl)propionic acid (ketoprofen) with histidine.

Journal: The journal of physical chemistry. B 20081127

Title: Two three-dimensional networks in the binary molecular adducts 4-methylimidazolium hydrogen terephthalate and bis(4-methylimidazolium) terephthalate.

Journal: Acta crystallographica. Section C, Crystal structure communications 20080601

Title: Bis-histidine-coordinated hemes in four-helix bundles: how the geometry of the bundle controls the axial imidazole plane orientations in transmembrane cytochromes of mitochondrial complexes II and III and related proteins.

Journal: Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20080501

Title: Hydrogen atom transfer reactions of iron-porphyrin-imidazole complexes as models for histidine-ligated heme reactivity.

Journal: Journal of the American Chemical Society 20080305

Title: Improved interaction potentials for charged residues in proteins.

Journal: The journal of physical chemistry. B 20080214

Title: Histidine protonation and the activation of viral fusion proteins.

Journal: Biochemical Society transactions 20080201

Title: Three-dimensional networks in 5-methylimidazolium 3-carboxy-4-hydroxybenzenesulfonate and bis(5-methylimidazolium) 3-carboxylato-4-hydroxybenzenesulfonate.

Journal: Acta crystallographica. Section C, Crystal structure communications 20080201

Title: Toxicity and carcinogenicity studies of 4-methylimidazole in F344/N rats and B6C3F1 mice.

Journal: Archives of toxicology 20080101

Title: Different protonation equilibria of 4-methylimidazole and acetic acid.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20071203

Title: Location of binding sites in small molecule rescue of human carbonic anhydrase II.

Journal: Biophysical journal 20070115

Title: Correlated proton motion in hydrogen bonded systems: tuning proton affinities.

Journal: Physical chemistry chemical physics : PCCP 20070114

Title: Toxicology and carcinogenesis studies of 4-methylimidazole (Cas No. 822-36-6) in F344/N rats and B6C3F1 mice (feed studies).

Journal: National Toxicology Program technical report series 20070101

Title: Variation of atomic charges on proton transfer in strong hydrogen bonds: the case of anionic and neutral imidazole-acetate complexes.

Journal: Journal of computational chemistry 20061115

Title: Supercritical fluid extraction (SFE) of 4(5)-methylimidazole (4-MeI) and 2-acetyl-4(5)-(1,2,3,4)-tetrahydroxybutyl-imidazole (THI) from ground-coffee with high-performance liquid chromatographic-electrospray mass spectrometric quantification (HPLC/ESI-MS).

Journal: Food additives and contaminants 20061001

Title: Proton transfer pathways in the mutant His-64-Ala of human carbonic anhydrase II.

Journal: Biopolymers 20060815

Title: Protonation and hydrogen-bonding state of the distal histidine in the CO complex of horseradish peroxidase as studied by ultraviolet resonance Raman spectroscopy.

Journal: Biochemistry 20060815

Title: Synthesis, reactivity, and X-ray crystal structure of some mixed-ligand oxovanadium(V) complexes: first report of binuclear oxovanadium(V) complexes containing 4,4'-bipyridine type bridge.

Journal: Inorganic chemistry 20060626

Title: A dynamic N-capping motif in cytochrome b5: evidence for a pH-controlled conformational switch.

Journal: Proteins 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Inhibition of histidine ammonia lyase by heteroaryl-alanines and acrylates.

Journal: Chemistry & biodiversity 20060501

Title: Induction of thyroid lesions in 14-week toxicity studies of 2 and 4-methylimidazole in Fischer 344/N rats and B6C3F1 mice.

Journal: Archives of toxicology 20060301

Title: Inhibitive properties and surface morphology of a group of heterocyclic diazoles as inhibitors for acidic iron corrosion.

Journal: Langmuir : the ACS journal of surfaces and colloids 20051220

Title: Prediction of CYP2C9-mediated drug-drug interactions: a comparison using data from recombinant enzymes and human hepatocytes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20051101

Title: NMR and theoretical study on the coordination and solution structures of the interaction between diperoxovanadate complexes and histidine-like ligands.

Journal: Inorganic chemistry 20050919

Title: Mechanisms of formation of 8-oxoguanine due to reactions of one and two OH* radicals and the H2O2 molecule with guanine: A quantum computational study.

Journal: The journal of physical chemistry. B 20050728

Title: Variation of geometries and electron properties along proton transfer in strong hydrogen-bond complexes.

Journal: The Journal of chemical physics 20050601

Title: Delamination and aromatic amine intercalation of layered aluminophosphate with [Al3P4O16]3- stoichiometry.

Journal: Journal of colloid and interface science 20050515

Title: Proton transfer from exogenous donors in catalysis by human carbonic anhydrase II.

Journal: Archives of biochemistry and biophysics 20050501

Title: Environmental effects on proton transfer in a strong hydrogen bond dimer: the 4-methyl-imidazole-aspartate case.

Journal: Physical chemistry chemical physics : PCCP 20050407

Title: Accurate prediction of absolute acidity constants in water with a polarizable force field: substituted phenols, methanol, and imidazole.

Journal: The journal of physical chemistry. B 20050331

Title: From model compounds to protein binding: syntheses, characterizations and fluorescence studies of [RuII(bipy)(terpy)L]2+ complexes (bipy = 2,2'-bipyridine; terpy = 2,2':6',2''-terpyridine; L = imidazole, pyrazole and derivatives, cytochrome c).

Journal: Dalton transactions (Cambridge, England : 2003) 20050121

Title: A strong positive dendritic effect in a peptide dendrimer-catalyzed ester hydrolysis reaction.

Journal: Journal of the American Chemical Society 20041208

Title: Lead and thallium tetrakis(imidazolyl)borates: modifying structure by varying metal and anion.

Journal: Inorganic chemistry 20040712

Title: NTP technical report on the toxicity studies of 2- and 4-Methylimidazole (CAS No. 693-98-1 and 822-36-6) administered in feed to F344/N rats and B6C3F1 mice.

Journal: Toxicity report series 20040401

Title: Chromophore selectivity in bacterial phytochromes: dissecting the process of chromophore attachment.

Journal: European journal of biochemistry 20040301

Title: The effects of substitution on tetrakis(substituted imidazole)copper(II) trifluoromethanesulfonates.

Journal: Acta crystallographica. Section C, Crystal structure communications 20031201

Title: Solvent and pH effects on fast and ultrasensitive 1,1'-oxalyldi(4-methyl)imidazole chemiluminescence.

Journal: The Analyst 20031001

Title: Effects of heterocyclic aromatic substituents on binding affinities at two distinct sites of somatostatin receptors. Correlation with the electrostatic potential of the substituents.

Journal: Journal of medicinal chemistry 20030508

Title: Oxovanadium(IV) and -(V) complexes of dithiocarbazate-based tridentate Schiff base ligands: syntheses, structure, and photochemical reactivity of compounds involving imidazole derivatives as coligands.

Journal: Inorganic chemistry 20030310

Title: The refined atomic structure of carbonic anhydrase II at 1.05 A resolution: implications of chemical rescue of proton transfer.

Journal: Acta crystallographica. Section D, Biological crystallography 20030101

Title: Direct infrared detection of the covalently ring linked His-Tyr structure in the active site of the heme-copper oxidases.

Journal: Biochemistry 20021203

Title: Gas chromatographic-mass spectrometric quantification of 4-(5-)methylimidazole in roasted coffee after ion-pair extraction.

Journal: Journal of chromatography. A 20021108

Title: Chemical rescue in catalysis by human carbonic anhydrases II and III.

Journal: Biochemistry 20020305

Title: Structural and kinetic analysis of the chemical rescue of the proton transfer function of carbonic anhydrase II.

Journal: Biochemistry 20010213

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Tags:822-36-6 Molecular Formula|822-36-6 MDL|822-36-6 SMILES|822-36-6 4-Methylimidazole |Organic_Building_Blocks