Home Other Building Blocks 4-Methylimidazole

4-Methylimidazole

CAS No.:
822-36-6
Catalog Number:
AG00343M
Molecular Formula:
C4H6N2
Molecular Weight:
82.1038
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
25g
98%
In Stock USA
United States
$25
- +
100g
98%
In Stock USA
United States
$63
- +
500g
98%
In Stock USA
United States
$188
- +
Product Description
Catalog Number:
AG00343M
Chemical Name:
4-Methylimidazole
CAS Number:
822-36-6
Molecular Formula:
C4H6N2
Molecular Weight:
82.1038
MDL Number:
MFCD01074774
IUPAC Name:
5-methyl-1H-imidazole
InChI:
InChI=1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)
InChI Key:
XLSZMDLNRCVEIJ-UHFFFAOYSA-N
SMILES:
Cc1c[nH]cn1
EC Number:
212-497-3
UNII:
Q64GF9FV4I
NSC Number:
40744
Properties
Complexity:
44.8  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
82.053g/mol
Formal Charge:
0
Heavy Atom Count:
6  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
82.106g/mol
Monoisotopic Mass:
82.053g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
28.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.2  
Literature
Title Journal
Switching orientation of two axial imidazole ligands between parallel and perpendicular in low-spin Fe(III) and Fe(II) nonplanar porphyrinates. Inorganic chemistry 20121105
Comparative risk assessment of carcinogens in alcoholic beverages using the margin of exposure approach. International journal of cancer 20120915
Re-evaluation of the proton affinity of 18-crown-6 using competitive threshold collision-induced dissociation techniques. Analytical chemistry 20120904
Accurate structure and dynamics of the metal-site of paramagnetic metalloproteins from NMR parameters using natural bond orbitals. Journal of the American Chemical Society 20120314
Self-assembly of the oxy-tyrosinase core and the fundamental components of phenolic hydroxylation. Nature chemistry 20120304
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 of agricultural and food chemistry 20120201
Structural and energetic effects in the molecular recognition of protonated peptidomimetic bases by 18-crown-6. Journal of the American Chemical Society 20120201
Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: application to the synthesis of nilotinib. Journal of the American Chemical Society 20120111
Determination of 4(5)-methylimidazole in soy sauce and other foods by LC-MS/MS after solid-phase extraction. Journal of agricultural and food chemistry 20110928
Reengineering rate-limiting, millisecond enzyme motions by introduction of an unnatural amino acid. Biophysical journal 20110720
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 of agricultural and food chemistry 20110427
Chemical rescue of enzymes: proton transfer in mutants of human carbonic anhydrase II. Journal of the American Chemical Society 20110427
Structure of rhomboid protease in a lipid environment. Journal of molecular biology 20110325
Protonation, tautomerization, and rotameric structure of histidine: a comprehensive study by magic-angle-spinning solid-state NMR. Journal of the American Chemical Society 20110209
Formation of carcinogenic 4(5)-methylimidazole in Maillard reaction systems. Journal of agricultural and food chemistry 20110126
Does 4-methylimidazole have tumor preventive activity in the rat? Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110101
Conformationally constrained histidines in the design of peptidomimetics: strategies for the χ-space control. International journal of molecular sciences 20110101
Structural studies of β-carbonic anhydrase from the green alga Coccomyxa: inhibitor complexes with anions and acetazolamide. PloS one 20110101
A comparative structural bioinformatics analysis of inherited mutations in β-D-Mannosidase across multiple species reveals a genotype-phenotype correlation. BMC genomics 20110101
Ligand effects on the [Cu(PhO)(PhOH)]+ redox active complex. Inorganic chemistry 20100920
A model study of the efficiency of the Asp-His-Ser triad. Journal of computational chemistry 20100715
Structural and mechanistic insights into the oxy form of tyrosinase from molecular dynamics simulations. Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20100201
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. Acta crystallographica. Section C, Crystal structure communications 20091201
DFT calculations of the EPR parameters for Cu(ii) DETA imidazole complexes. Physical chemistry chemical physics : PCCP 20091001
Three-dimensional networks in bis(imidazolium) 2,2'-dithiodibenzoate and 4-methylimidazolium 2-[(2-carboxyphenyl)disulfanyl]benzoate. Acta crystallographica. Section C, Crystal structure communications 20090901
Histidine side-chain dynamics and protonation monitored by 13C CPMG NMR relaxation dispersion. Journal of biomolecular NMR 20090801
Light-induced oxidation of tryptophan and histidine. Reactivity of aromatic N-heterocycles toward triplet-excited flavins. Journal of the American Chemical Society 20090617
Microfluidic device capable of sensing ultrafast chemiluminescence. Talanta 20090515
Comparative analysis of mutant tyrosine kinase chemical rescue. Biochemistry 20090421
Effects of 4-methylimidazole on cerebral glutamate decarboxylase activity and specific GABA receptor binding in mice. Toxicology mechanisms and methods 20090301
Bis(4-methyl-imidazolium) succinate succinic acid solvate. Acta crystallographica. Section E, Structure reports online 20090301
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 of molecular graphics & modelling 20090101
Structures of human cytochrome P-450 2E1. Insights into the binding of inhibitors and both small molecular weight and fatty acid substrates. The Journal of biological chemistry 20081128
Reaction dynamics of excited 2-(3-benzoylphenyl)propionic acid (ketoprofen) with histidine. The journal of physical chemistry. B 20081127
Two three-dimensional networks in the binary molecular adducts 4-methylimidazolium hydrogen terephthalate and bis(4-methylimidazolium) terephthalate. Acta crystallographica. Section C, Crystal structure communications 20080601
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 of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20080501
Hydrogen atom transfer reactions of iron-porphyrin-imidazole complexes as models for histidine-ligated heme reactivity. Journal of the American Chemical Society 20080305
Improved interaction potentials for charged residues in proteins. The journal of physical chemistry. B 20080214
Histidine protonation and the activation of viral fusion proteins. Biochemical Society transactions 20080201
Three-dimensional networks in 5-methylimidazolium 3-carboxy-4-hydroxybenzenesulfonate and bis(5-methylimidazolium) 3-carboxylato-4-hydroxybenzenesulfonate. Acta crystallographica. Section C, Crystal structure communications 20080201
Toxicity and carcinogenicity studies of 4-methylimidazole in F344/N rats and B6C3F1 mice. Archives of toxicology 20080101
Different protonation equilibria of 4-methylimidazole and acetic acid. Chemphyschem : a European journal of chemical physics and physical chemistry 20071203
Location of binding sites in small molecule rescue of human carbonic anhydrase II. Biophysical journal 20070115
Correlated proton motion in hydrogen bonded systems: tuning proton affinities. Physical chemistry chemical physics : PCCP 20070114
Toxicology and carcinogenesis studies of 4-methylimidazole (Cas No. 822-36-6) in F344/N rats and B6C3F1 mice (feed studies). National Toxicology Program technical report series 20070101
Variation of atomic charges on proton transfer in strong hydrogen bonds: the case of anionic and neutral imidazole-acetate complexes. Journal of computational chemistry 20061115
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). Food additives and contaminants 20061001
Proton transfer pathways in the mutant His-64-Ala of human carbonic anhydrase II. Biopolymers 20060815
Protonation and hydrogen-bonding state of the distal histidine in the CO complex of horseradish peroxidase as studied by ultraviolet resonance Raman spectroscopy. Biochemistry 20060815
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. Inorganic chemistry 20060626
A dynamic N-capping motif in cytochrome b5: evidence for a pH-controlled conformational switch. Proteins 20060501
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Inhibition of histidine ammonia lyase by heteroaryl-alanines and acrylates. Chemistry & biodiversity 20060501
Induction of thyroid lesions in 14-week toxicity studies of 2 and 4-methylimidazole in Fischer 344/N rats and B6C3F1 mice. Archives of toxicology 20060301
Inhibitive properties and surface morphology of a group of heterocyclic diazoles as inhibitors for acidic iron corrosion. Langmuir : the ACS journal of surfaces and colloids 20051220
Prediction of CYP2C9-mediated drug-drug interactions: a comparison using data from recombinant enzymes and human hepatocytes. Drug metabolism and disposition: the biological fate of chemicals 20051101
NMR and theoretical study on the coordination and solution structures of the interaction between diperoxovanadate complexes and histidine-like ligands. Inorganic chemistry 20050919
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. The journal of physical chemistry. B 20050728
Variation of geometries and electron properties along proton transfer in strong hydrogen-bond complexes. The Journal of chemical physics 20050601
Delamination and aromatic amine intercalation of layered aluminophosphate with [Al3P4O16]3- stoichiometry. Journal of colloid and interface science 20050515
Proton transfer from exogenous donors in catalysis by human carbonic anhydrase II. Archives of biochemistry and biophysics 20050501
Environmental effects on proton transfer in a strong hydrogen bond dimer: the 4-methyl-imidazole-aspartate case. Physical chemistry chemical physics : PCCP 20050407
Accurate prediction of absolute acidity constants in water with a polarizable force field: substituted phenols, methanol, and imidazole. The journal of physical chemistry. B 20050331
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). Dalton transactions (Cambridge, England : 2003) 20050121
A strong positive dendritic effect in a peptide dendrimer-catalyzed ester hydrolysis reaction. Journal of the American Chemical Society 20041208
Lead and thallium tetrakis(imidazolyl)borates: modifying structure by varying metal and anion. Inorganic chemistry 20040712
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. Toxicity report series 20040401
Chromophore selectivity in bacterial phytochromes: dissecting the process of chromophore attachment. European journal of biochemistry 20040301
The effects of substitution on tetrakis(substituted imidazole)copper(II) trifluoromethanesulfonates. Acta crystallographica. Section C, Crystal structure communications 20031201
Solvent and pH effects on fast and ultrasensitive 1,1'-oxalyldi(4-methyl)imidazole chemiluminescence. The Analyst 20031001
Effects of heterocyclic aromatic substituents on binding affinities at two distinct sites of somatostatin receptors. Correlation with the electrostatic potential of the substituents. Journal of medicinal chemistry 20030508
Oxovanadium(IV) and -(V) complexes of dithiocarbazate-based tridentate Schiff base ligands: syntheses, structure, and photochemical reactivity of compounds involving imidazole derivatives as coligands. Inorganic chemistry 20030310
The refined atomic structure of carbonic anhydrase II at 1.05 A resolution: implications of chemical rescue of proton transfer. Acta crystallographica. Section D, Biological crystallography 20030101
Direct infrared detection of the covalently ring linked His-Tyr structure in the active site of the heme-copper oxidases. Biochemistry 20021203
Gas chromatographic-mass spectrometric quantification of 4-(5-)methylimidazole in roasted coffee after ion-pair extraction. Journal of chromatography. A 20021108
Chemical rescue in catalysis by human carbonic anhydrases II and III. Biochemistry 20020305
Structural and kinetic analysis of the chemical rescue of the proton transfer function of carbonic anhydrase II. Biochemistry 20010213
Properties