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I2399 Sigma-Aldrich

Imidazole

ACS reagent, ≥99% (titration)

Synonym: 1,3-Diaza-2,4-cyclopentadiene, Glyoxaline

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Properties

Related Categories ACS Grade Buffers, Biochemicals and Reagents, Biological Buffers, Buffers A to Z, Building Blocks,
grade   ACS reagent
vapor pressure   <1 mmHg ( 20 °C)
assay   ≥99% (titration)
impurities   ≤0.2% water
ign. residue   ≤0.1%
pH   9.5-11.0 (25 °C, 5% in H2O)
pKa (25 °C)   6.95
bp   256 °C(lit.)
mp   88-91 °C(lit.)
cation traces   Fe: ≤0.001%

Description

Application

Excellent for buffers in the range of pH 6.2-7.8

Packaging

100, 500 g in glass bottle

Legal Information

Redi-Dri is a trademark of Sigma-Aldrich Co. LLC

Other Notes

Go to Redi-Dri Product Listing 792527

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3263 8 / PGII
WGK Germany 
2
RTECS 
NI3325000
Flash Point(F) 
293 °F
Flash Point(C) 
145 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Determination of Water Content in Imidazole Using Karl Fischer Titration

Nitrogen compounds, acid amides and weakly basic amines (heterocyclenes) give no problems. They can be titrated according to the standard procedures. Strongly basic amines alter the pH value and must...
Keywords: Titrations

Peer-Reviewed Papers

References

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Review: As RNase model. R. Breslow Acc. Chem. Res. 24, 317, (1991)

Adapting fluorescence resonance energy transfer with quantum dot donors for solid-phase hybridization assays in microtiter plate format. Petryayeva E, Algar WR, and Krull UJ Langmuir 29(3), 977-87, (2013)

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Biotransformations of anticancer ruthenium(III) complexes: an X-ray absorption spectroscopic study. Levina A, Aitken JB, Gwee YY, et al. Chemistry 19(11), 3609-19, (2013)

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Design of a new fluorescent probe: pyrrole/imidazole hairpin polyamides with pyrene conjugation at their γ-turn. Vaijayanthi T, Bando T, Hashiya K, et al. Bioorg. Med. Chem. 21(4), 852-5, (2013)

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Anti-Plasmodium activity of imidazolium and triazolium salts. Jason Z Vlahakis et al Bioorg. Med. Chem. 18, 6184-96, (2010)

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Measurement of histidine pKa values and tautomer populations in invisible protein states. Hansen AL and Kay LE Proc. Natl. Acad. Sci. U. S. A. 111(17), E1705-12, (2014)

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Characterization of two members among the five ADP-forming acyl coenzyme A (Acyl-CoA) synthetases reveals the presence of a 2-(Imidazol-4-yl)acetyl-CoA synthetase in Thermococcus kodakarensis. Awano T, Wilming A, Tomita H, et al. J. Bacteriol. 196(1), 140-7, (2014)

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Extracellular delivery of modified oligonucleotide and superparamagnetic iron oxide nanoparticles from a degradable hydrogel triggered by tumor acidosis. Lin CW, Tseng SJ, Kempson IM, et al. Biomaterials 34(17), 4387-93, (2013)

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Substrate specificity of an oxygen dependent sulfoxide synthase in ovothiol biosynthesis. Mashabela GT and Seebeck FP Chem. Commun. (Camb.) 49(70), 7714-6, (2013)

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Heme exporter FLVCR1a regulates heme synthesis and degradation and controls activity of cytochromes P450. Vinchi F, Ingoglia G, Chiabrando D, et al. Gastroenterology 146(5), 1325-38, (2014)

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Identification of a pKa-regulating motif stabilizing imidazole-modified double-stranded DNA. Buyst D, Gheerardijn V, Fehér K, et al. Nucleic Acids Res. 43(1), 51-62, (2015)

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[Reactive oxygen forms and Ca ions as possible intermediaries under the induction of heat resistance of plant cells by jasmonic acid]. Karpets IuV, Kolupaev IuE, Iastreb TO, et al. Ukr. Biokhim. Zh. 85(3), 62-8, (2013)

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[Participation of the active oxygen forms in the induction of ascorbate peroxidase and guaiacol peroxidase under heat hardening of wheat seedlings]. Kolupaev IuE and Oboznyĭ AI Ukr. Biokhim. Zh. 84(6), 131-8, (2012)

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Revisiting G3BP1 as a RasGAP Binding Protein: Sensitization of Tumor Cells to Chemotherapy by the RasGAP 317-326 Sequence Does Not Involve G3BP1. Alessandro Annibaldi et al PLoS ONE 6, e29024, (2011)

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Recognition of the DNA minor groove by pyrrole-imidazole polyamides. Dervan PB and Edelson BS Curr. Opin. Struct. Biol. 13(3), 284-99, (2003)

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Antitumor activity of a pyrrole-imidazole polyamide. Yang F, Nickols NG, Li BC, et al. Proc. Natl. Acad. Sci. U. S. A. 110(5), 1863-8, (2013)

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Development and evaluation of new imidazolium-based zwitterionic stationary phases for hydrophilic interaction chromatography. Qiao L, Dou A, Shi X, et al. J. Chromatogr. A 1286, 137-45, (2013)

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Selective inhibition of glycosyltransferases by bivalent imidazolium salts. Gao Y, Vlahakis JZ, Szarek WA, et al. Bioorg. Med. Chem. 21(5), 1305-11, (2013)

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IMPa-4, an Arabidopsis importin alpha isoform, is preferentially involved in agrobacterium-mediated plant transformation. Bhattacharjee S Plant Cell 20(10), 2661-80, (2008)

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RNA-protein analysis using a conditional CRISPR nuclease. Lee HY, Haurwitz RE, Apffel A, et al. Proc. Natl. Acad. Sci. U. S. A. 110(14), 5416-21, (2013)

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Covalent bonding of zeolitic imidazolate framework-90 to functionalized silica fibers for solid-phase microextraction. Yu LQ and Yan XP Chem. Commun. (Camb.) 49(21), 2142-4, (2013)

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Resonance Raman and electrocatalytic behavior of thiolate and imidazole bound iron porphyrin complexes on self assembled monolayers: functional modeling of cytochrome P450. Sengupta K, Chatterjee S, Samanta S, et al. Inorg. Chem. 52(4), 2000-14, (2013)

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Structural and biological studies on bacterial nitric oxide synthase inhibitors. Holden JK, Li H, Jing Q, et al. Proc. Natl. Acad. Sci. U. S. A. 110(45), 18127-31, (2013)

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A family of single-isomer, dicationic cyclodextrin chiral selectors for capillary electrophoresis: mono-6(A)-ammonium-6(C)-butylimidazolium-β-cyclodextrin chlorides. Dai Y, Wang S, Zhou J, et al. Electrophoresis 34(6), 833-40, (2013)

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Oral versus intra-vaginal imidazole and triazole anti-fungal agents for the treatment of uncomplicated vulvovaginal candidiasis (thrush): a systematic review. Watson MC, Grimshaw JM, Bond CM, et al. BJOG 109(1), 85-95, (2002)

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Synthetic methodology utilized to prepare substituted imidazole p38 MAP kinase inhibitors. Murry JA Curr. Opin. Drug Discov. Devel. 6(6), 945-65, (2003)

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Kinetics and mechanism of imidazole-catalyzed acylation of cellulose in LiCl/N,N-dimethylacetamide. Nawaz H, Pires PA, and El Seoud OA Carbohydr. Polym. 92(2), 997-1005, (2013)

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Sequence-selective detection of double-stranded DNA sequences using pyrrole-imidazole polyamide microarrays. Singh I, Wendeln C, Clark AW, et al. J. Am. Chem. Soc. 135(9), 3449-57, (2013)

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Layer selection effect on solid state 13C and 15N chemical shifts calculation using ONIOM approach. Shaghaghi H, Ebrahimi HP, Bahrami Panah N, et al. Solid State Nucl. Magn. Reson. 51-52, 31-6, (2013)

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Medicinal chemistry and biological properties of non-imidazole histamine H3 antagonists. Cowart M, Altenbach R, Black L, et al. Mini Rev. Med. Chem. 4(9), 979-92, (2004)

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N-terminal processing of proteins exported by malaria parasites Chang,H et al. Mol. Biochem. Parasitol. 160(2), 107-115, (2008)

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Medicinal chemical and pharmacological aspects of imidazole-containing histamine H3 receptor antagonists. Stark H, Kathmann M, Schlicker E, et al. Mini Rev. Med. Chem. 4(9), 965-77, (2004)

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A nondesensitizing kainate receptor point mutant. Nayeem N Mol. Pharmacol. 76(3), 534-42, (2009)

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Fluorogenic dansyl-ligated gold nanoparticles for the detection of sulfur mustard by displacement assay. Knighton RC, Sambrook MR, Vincent JC, et al. Chem. Commun. (Camb.) 49(23), 2293-5, (2013)

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Electrocatalytic O2 reduction reaction by synthetic analogues of cytochrome P450 and myoglobin: in-situ resonance Raman and dynamic electrochemistry investigations. Chatterjee S, Sengupta K, Samanta S, et al. Inorg. Chem. 52(17), 9897-907, (2013)

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Animal toxicity of hairpin pyrrole-imidazole polyamides varies with the turn unit. Yang F, Nickols NG, Li BC, et al. J. Med. Chem. 56(18), 7449-57, (2013)

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Spectroscopic studies on the interactions between imidazolium chloride ionic liquids and bovine serum albumin. Huang R, Zhang S, Pan L, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 104, 377-82, (2013)

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Noncovalent interactions in halogenated ionic liquids: theoretical study and crystallographic implications. Li H, Lu Y, Wu W, et al. Phys. Chem. Chem. Phys. 15(12), 4405-14, (2013)

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Dissolution and depolymerization of barley starch in selected ionic liquids. Lappalainen K, Kärkkäinen J, and Lajunen M Carbohydr. Polym. 93(1), 89-94, (2013)

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Chiral profiling of azole antifungals in municipal wastewater and recipient rivers of the Pearl River Delta, China. Huang Q, Wang Z, Wang C, et al. Environ. Sci. Pollut. Res. Int. 20(12), 8890-9, (2013)

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Siderophore-mediated iron acquisition systems in Bacillus cereus: Identification of receptors for anthrax virulence-associated petrobactin . Zawadzka AM Biochemistry 48(16), 3645-57, (2009)

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P38 MAP kinase inhibitors: evolution of imidazole-based and pyrido-pyrimidin-2-one lead classes. Natarajan SR and Doherty JB Curr. Top. Med. Chem 5(10), 987-1003, (2005)

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Contact dermatitis due to imidazole antimycotics. Guidetti MS, Vincenzi C, Guerra L, et al. Contact Dermatitis 33(4), 282, (1995)

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Transducer influence of polycyclic aromatic hydrocarbons (PAHs) on photoisomerisation of 1-alkyl-2-(arylazo)imidazoles. Gayen P and Sinha C Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 104, 477-85, (2013)

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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. Berry EA and Walker FA J. Biol. Inorg. Chem. 13(4), 481-98, (2008)

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The heme environment of mouse neuroglobin: histidine imidazole plane orientations obtained from solution NMR and EPR spectroscopy as compared with X-ray crystallography. Walker FA J. Biol. Inorg. Chem. 11(4), 391-7, (2006)

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Potent BRAF kinase inhibitors based on 2,4,5-trisubstituted imidazole with naphthyl and benzothiophene 4-substituents. Niculescu-Duvaz D, Niculescu-Duvaz I, Suijkerbuijk BM, et al. Bioorg. Med. Chem. 21(5), 1284-304, (2013)

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Temperature and acid-base balance in ectothermic vertebrates: the imidazole alphastat hypotheses and beyond. Burton RF J. Exp. Biol. 205(Pt 23), 3587-600, (2002)

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Recent developments of p38α MAP kinase inhibitors as antiinflammatory agents based on the imidazole scaffolds. Kong TT, Zhang CM, and Liu ZP Curr. Med. Chem. 20(15), 1997-2016, (2013)

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Structure and nature of manganese(II) imidazole complexes in frozen aqueous solutions. Un S Inorg. Chem. 52(7), 3803-13, (2013)

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Effects of imidazole deprotonation on vibrational spectra of high-spin iron(II) porphyrinates. Hu C, Peng Q, Silvernail NJ, et al. Inorg. Chem. 52(6), 3170-7, (2013)

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Sec3-containing exocyst complex is required for desmosome assembly in mammalian epithelial cells. Nicholas J. Andersen et al Mol. Biol. Cell 21, 152-64, (2010)

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Design, synthesis and aromatase inhibitory activities of novel indole-imidazole derivatives. Wang R, Shi HF, Zhao JF, et al. Bioorg. Med. Chem. Lett. 23(6), 1760-2, (2013)

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A point mutation produced a class 3 aldehyde dehydrogenase with increased protective ability against the killing effect of cyclophosphamide. Ho KK Biochem. Pharmacol. 76(5), 690-6, (2008)

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Axial ligand replacement mechanism in heme transfer from streptococcal heme-binding protein Shp to HtsA of the HtsABC transporter. Ran Y, Malmirchegini GR, Clubb RT, et al. Biochemistry 52(37), 6537-47, (2013)

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Muscarine, imidazole, and peptide alkaloids, and other miscellaneous alkaloids. Lewis JR Nat. Prod. Rep. 3(6), 587-90, (1986)

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Metal-free, acid-promoted synthesis of imidazole derivatives via a multicomponent reaction. Chen CY, Hu WP, Yan PC, et al. Org. Lett. 15(24), 6116-9, (2013)

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Analysis of physico-chemical properties of substrates of ABC and MFS multidrug transporters of pathogenic Candida albicans. Nidhi Puri et al Eur. J. Med. Chem. 45, 4813-26, (2010)

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Organic-inorganic hybrids of imidazole complexes of zinc (II) for catalysts in the glycerolysis of urea. Kim DW and Park DW J. Nanosci. Nanotechnol. 14(6), 4632-8, (2014)

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Stabilizing effect of electrostatic vs. aromatic interactions in diproline nucleated peptide β-hairpins. Makwana KM, Raghothama S, and Mahalakshmi R Phys. Chem. Chem. Phys. 15(37), 15321-4, (2013)

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Design, synthesis, and evaluation of potential inhibitors of nitric oxide synthase. Tania Castaño et al Bioorg. Med. Chem. 16, 6193-206, (2008)

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Convenient syntheses of cyanuric chloride-derived NHC ligands, their Ag(I) and Au(I) complexes and antimicrobial activity. Almalioti F, MacDougall J, Hughes S, et al. Dalton Trans. 42(34), 12370-80, (2013)

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Triazolo and imidazo dihydropyrazolopyrimidine potassium channel antagonists. Finlay HJ, Jiang J, Caringal Y, et al. Bioorg. Med. Chem. Lett. 23(6), 1743-7, (2013)

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Preliminary extraction of tannins by 1-butyl-3-methylimidazole bromide and its subsequent removal from Galla chinensis extract using macroporous resins. Lu C, Luo X, Lu L, et al. J. Sep. Sci. 36(5), 959-64, (2013)

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Novel luminescent hybrids by incorporating rare earth β-diketonates into polymers through ion pairing with an imidazolium counter ion. Li QP and Yan B Photochem. Photobiol. Sci. 12(9), 1628-35, (2013)

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Luminescent pH sensor of a novel imidazole-containing hexanuclear Ru(II) polypyridyl complex. Cheng F, Tang N, Chen J, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 114, 159-63, (2013)

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Identification of proximal and distal axial ligands in Leishmania major pseudoperoxidase. Saha R, Bose M, Sen Santara S, et al. Biochemistry 52(49), 8878-87, (2013)

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Hx-amides: DNA sequence recognition by the fluorescent Hx (p-anisylbenzimidazole)•pyrrole and Hx•imidazole pairings. Satam V, Patil P, Babu B, et al. Bioorg. Med. Chem. Lett. 23(6), 1699-702, (2013)

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Non-benzimidazole containing inhibitors of respiratory syncytial virus. Pryde DC, Tran TD, Gardner I, et al. Bioorg. Med. Chem. Lett. 23(3), 827-33, (2013)

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H93G myoglobin cavity mutant as versatile template for modeling heme proteins: magnetic circular dichroism studies of thiolate- and imidazole-ligated complexes. Dawson JH, Pond AE, and Roach MP Biopolymers 67(4-5), 200-6, (2002)

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New concept in nutrition for the maintenance of the aging eye redox regulation and therapeutic treatment of cataract disease; synergism of natural antioxidant imidazole-containing amino acid-based compounds, chaperone, and glutathione boosting agents: a systemic perspective on aging and longevity emerged from studies in humans. Babizhayev MA Am. J. Ther. 17(4), 373-89, (2010)

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Synthesis of new optically active 2-pyrrolidinones. Moutevelis-Minakakis P, Papavassilopoulou E, and Mavromoustakos T Molecules 18(1), 50-73, (2012)

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Designation of imidazole-containing dipeptides as pharmacological chaperones. Babizhayev MA Hum. Exp. Toxicol. 30(7), 736-61, (2011)

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Imidazole-induced contractility of vascular smooth muscle cells in the presence of U-73122, ODQ, indomethacin and 7-nitroindazole. Wiciński M, Grześk G, Malinowski B, et al. Pol. J. Vet. Sci. 16(2), 293-7, (2013)

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Human poisoning with prochloraz imidazole fungicide. Chen HH, Lin JL, Yen TH, et al. Clin. Toxicol. (Phila.) 51(10), 1237-8, (2013)

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Merck 14,4912

Beil. 23,V,4,191

Fieser 1,492 / Fieser 2,220

Aldrich MSDS 1, 1083:B / Corp MSDS 1 (1), 1973:D / FT-IR 2 (3), 3503:B / FT-IR 1 (2), 611:D / FT-NMR 1 (3), 75:B / IR-Spectra (3), 1217:G / IR-Spectra (2), 1060:E / NMR-Reference 2 (2), 484:D / RegBook 1 (2), 2351:A / Sax 6, 1605 / Sigma FT-IR 1 (2), 648:C / Structure Index 1, 371:D:6 / Vapor Phase 3, 1483:C

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