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M50834 Aldrich

1-Methylimidazole Green Alternative

ReagentPlus®, 99%

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Properties

Related Categories 12 Principles Aligned Products, A to C, Biochemicals and Reagents, Building Blocks, C3 to C8,
grade   ReagentPlus®
vapor pressure   0.4 mmHg ( 20 °C)
assay   99%
autoignition temp.   977 °F
expl. lim.   15.7 %
greener alternative product characteristics   Catalysis
Learn more about the Principles of Green Chemistry.
refractive index   n20/D 1.495(lit.)
bp   198 °C(lit.)
mp   −6 °C(lit.)
density   1.03 g/mL at 25 °C(lit.)

Description

Packaging

100, 500 g in glass bottle

3 kg in glass bottle

Application

Co-catalyst for copper-catalyzed, greener oxidation of alcohols under aerobic conditions.

Copper(I)/ABNO-Catalyzed Aerobic Alcohol Oxidation: Alleviating Steric and Electronic Constraints of Cu/TEMPO Catalyst Systems

General description

Sigma Life Science is committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for energy efficiency. Find details here.

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3267 8 / PGII
WGK Germany 
1
RTECS 
NI7000000
Flash Point(F) 
197.6 °F
Flash Point(C) 
92 °C
Protocols & Articles

Articles

Determination of Water Content in 1-Methyl 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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Steam explosion distinctively enhances biomass enzymatic saccharification of cotton stalks by largely reducing cellulose polymerization degree in G. barbadense and G. hirsutum. Huang Y, Wei X, Zhou S, et al. Bioresour. Technol. 181, 224-30, (2015)

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Homoleptic and heteroleptic N-alkylimidazole zinc(ii)-containing ionic liquids for high current density electrodeposition. Steichen M, Brooks NR, Van Meervelt L, et al. Dalton Trans. 43(32), 12329-41, (2014)

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Cysteamine-palladium complex ([Pd(?-OAc)(ppy)]2, ppy:2-phenylpyridine, PhMe)-modified peroxidase biosensor immobilized on a gold electrode. Akyilmaz E, Günay ME, Asav E, et al. Artif. Cells. Nanomed. Biotechnol. 42(6), 413-7, (2014)

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Detection of virgin coconut oil adulteration with animal fats using quantitative cholesterol by GC × GC-TOF/MS analysis. Xu B, Li P, Ma F, et al. Food Chem. 178, 128-35, (2015)

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A novel miR-451a isomiR, associated with amelanotypic phenotype, acts as a tumor suppressor in melanoma by retarding cell migration and invasion. Babapoor S, Fleming E, Wu R, et al. PLoS ONE 9(9), e107502, (2014)

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Invoking pairwise interactions in water-promoted Diels-Alder reactions by using ionic liquids as cosolvents. Manna A, Kumar A, et al. ChemPhysChem 15(14), 3067-77, (2014)

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Isolation and characterization of feruloylated arabinoxylan oligosaccharides from the perennial cereal grain intermediate wheat grass (Thinopyrum intermedium). Schendel RR, Becker A, Tyl CE, et al. Carbohydr. Res. 407, 16-25, (2015)

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[PMIM]Br@TiO2 nanocomposite reinforced hollow fiber solid/liquid phase microextraction: an effective extraction technique for measurement of benzodiazepines in hair, urine and wastewater samples combined with high-performance liquid chromatography. Es'haghi Z, Nezhadali A, Bahar S, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 980, 55-64, (2015)

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p47phox and reactive oxygen species production modulate expression of microRNA-451 in macrophages. Ranjan R, Lee YG, Karpurapu M, et al. Free Radic. Res. 49(1), 25-34, (2014)

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Development of poly (I:C) modified doxorubicin loaded magnetic dendrimer nanoparticles for targeted combination therapy. Khodadust R, Unsoy G, Gunduz U, et al. Biomed. Pharmacother. 68(8), 979-87, (2014)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Transcriptional inhibition of progressive renal disease by gene silencing pyrrole-imidazole polyamide targeting of the transforming growth factor-β1 promoter. Matsuda H, Fukuda N, Ueno T, et al. Kidney Int. 79(1), 46-56, (2011)

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Development of programmable small DNA-binding molecules with epigenetic activity for induction of core pluripotency genes. Pandian GN, Ohtsuki A, Bando T, et al. Bioorg. Med. Chem. 20(8), 2656-60, (2012)

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Evaluation of PI polyamide conjugates with eight-base pair recognition and improvement of the aqueous solubility by PEGylation. Takagaki T, Bando T, Kitano M, et al. Bioorg. Med. Chem. 19(19), 5896-902, (2011)

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Direct arylation of simple azoles catalyzed by 1,10-phenanthroline containing palladium complexes: an investigation of C4 arylation of azoles and the synthesis of triarylated azoles by sequential arylation. Shibahara F, Yamaguchi E, and Murai T J. Org. Chem. 76(8), 2680-93, (2011)

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N-heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids. Wang ZY, Chen GQ, and Shao LX J. Org. Chem. 77(15), 6608-14, (2012)

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N-methylimidazolium-functionalized monolithic silica column for mixed-mode chromatography. Zhang P, Chen J, and Jia L J. Chromatogr. A. 1218(22), 3459-65, (2011)

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Ionic liquids supported on magnetic nanoparticles as a sorbent preconcentration material for sulfonylurea herbicides prior to their determination by capillary liquid chromatography. Bouri M, Gurau M, Salghi R, et al. Anal. Bioanal. Chem 404(5), 1529-38, (2012)

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N-heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed amination between aryl chlorides and amides. Chen WX and Shao LX J. Org. Chem. 77(20), 9236-9, (2012)

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One-pot sequential direct C-H bond arylation of azoles catalyzed by [Pd(phen)2](PF6)2: synthetic methods for triarylated azoles. Shibahara F, Yamauchi T, Yamaguchi E, et al. J. Org. Chem. 77(19), 8815-20, (2012)

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Comparative chemometric modeling of cytochrome 3A4 inhibitory activity of structurally diverse compounds using stepwise MLR, FA-MLR, PLS, GFA, G/PLS and ANN techniques. Kunal Roy et al Eur. J. Med. Chem. 44, 2913-22, (2009)

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Effect of solvation on ion binding to imidazole and methylimidazole. Sharma B, Rao JS, and Sastry GN J. Phys. Chem. A 115(10), 1971-84, (2011)

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Transformation of the {Fe(NO)2}9 dinitrosyl iron complexes (DNICs) into S-nitrosothiols (RSNOs) triggered by acid-base pairs. Tsou CC and Liaw WF Chemistry 17(47), 13358-66, (2011)

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N-Methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the Lossen rearrangement. Yoganathan S and Miller SJ Org. Lett. 15(3), 602-5, (2013)

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Setting anchor in the minor groove: in silico investigation into formamido N-methylpyrrole and N-methylimidazole polyamides bound by cognate DNA sequences. Collar CJ, Lee M, and Wilson WD J. Chem. Inf. Model. 50(9), 1611-22, (2010)

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One-pot synthesis of N-methylimidazolium-based porous polymer monolith for capillary electrochromatography via free radical copolymerization and quaterisation. Li Y, Chen Y, Wang K, et al. Electrophoresis 33(13), 2005-11, (2012)

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1-Methylimidazolium hydrogen sulfate catalyzed convenient synthesis of 2,5-dimethyl-N-substituted pyrroles under ultrasonic irradiation. Li D, Zang H, Wu C, et al. Ultrason. Sonochem. 20(5), 1144-8, (2013)

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A general strategy for the experimental study of the thermochemistry of protic ionic liquids: enthalpy of formation and vaporisation of 1-methylimidazolium ethanoate. Vitorino J, Bernardes CE, and Minas da Piedade ME Phys. Chem. Chem. Phys. 14(13), 4440-6, (2012)

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Inhibition of peroxynitrite- and peroxidase-mediated protein tyrosine nitration by imidazole-based thiourea and selenourea derivatives. Bhabak KP, Satheeshkumar K, Jayavelu S, et al. Org. Biomol. Chem. 9(21), 7343-50, (2011)

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Synthesis of resins with ionic liquids for purification of flavonoids from Hippophae rhamnoides L. leaves. Lou S and Di D J. Agric. Food Chem. 60(26), 6546-58, (2012)

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Reactions of the cationic zinc thiolate model complex [Zn(Tab)4](PF6)2 with N-donor ligands and cobalt dichloride. Zheng AX, Si J, Tang XY, et al. Inorg. Chem. 51(19), 10262-73, (2012)

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Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors. Srinivas Kantevari et al Bioorg. Med. Chem. 19, 4772-81, (2011)

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Modulating the synthetase activity of penicillin G acylase in organic media by addition of N-methylimidazole: using vinyl acetate as activated acyl donor. Liu B, Wu Q, Lv D, et al. J. Biotechnol. 153(3-4), 111-5, (2011)

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Homogeneous acylation of eucalyptus wood at room temperature in dimethyl sulfoxide/N-methylimidazole. Zhang AP, Liu CF, Sun RC, et al. Bioresour. Technol. 125, 328-31, (2012)

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Research on the adsorption property of supported ionic liquids for ferulic acid, caffeic acid and salicylic acid. Du N, Cao S, and Yu Y J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 879(19), 1697-703, (2011)

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Binding of imidazole to the heme of cytochrome c1 and inhibition of the bc1 complex from Rhodobacter sphaeroides: II. Kinetics and mechanism of binding. Kokhan O, Shinkarev VP, and Wraight CA J. Biol. Chem. 285(29), 22522-31, (2010)

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Determination of dihydroxyacetone and glycerol in fermentation process by GC after n-methylimidazole catalyzed acetylation. Wu J, Li MH, Lin JP, et al. J. Chromatogr. Sci. 49(5), 375-8, (2011)

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Investigation of non-covalent interaction of ANF promoter DNA and polyamides containing N-methylimidazole and N-methylpyrrole amino acids by electrospray ionization mass spectrometry. He X, Li S, Xu M, et al. Rapid Commun. Mass Spectrom. 25(7), 993-6, (2011)

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Beil. 23,V,4,256

Fieser 5,447

Aldrich MSDS 1, 1261:C / Corp MSDS 1 (2), 2368:C / FT-IR 1 (2), 612:B / FT-IR 2 (3), 3504:B / FT-NMR 1 (3), 76:A / IR-Spectra (2), 1060:F / IR-Spectra (3), 1218:A / NMR-Reference 2 (2), 485:A / RegBook 1 (2), 2351:D / Sax 6, 1862 / Sigma FT-IR 1 (2), 735:D / Structure Index 1, 371:D:7 / Vapor Phase 3, 1483:D

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