1-methyl-1H-imidazole

• ChemBase ID: 2397
• Molecular Formular: C4H6N2
• Molecular Mass: 82.10384
• Monoisotopic Mass: 82.0530982
• SMILES: Cn1ccnc1
• Canonical SMILES: Cn1cncc1
• InChI: InChI=1S/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3
• InChIKey: MCTWTZJPVLRJOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-1H-imidazole
• IUPAC Traditional name: 1-methylimidazole
• Synonyms: 1-methyl-1H-imidazole; N-Methylimidazole; Cap B (1-methylimidazole 12% in acetonitrile/pyridine 78 : 10); 1-Methylimidazole solution; Cap B (1-methylimidazole 10% in THF); Cap B (1-methylimidazole 10% in THF/pyridine 8 : 1); Cap B (1-methylimidazole 16% in THF); 1-Methylimidazole; 1-Methylimidazole; 1-Methyl-1H-imidazole 99%; N-METHYLIMIDAZOLE; 1-Methyl-1H-imidazole; Araldite DY 070; DY 070; N1-Methylimidazole; NSC 88064; 1-甲基咪唑 溶液; Cap B （10% 1-甲基咪唑溶于 THF）; 1-甲基咪唑 溶液; 1-甲基咪唑

Database IDs

• CAS Number: 616-47-7
• EC Number: 210-484-7
• MDL Number: MFCD00005292
• Beilstein Number: 105197
• PubChem SID: 160965848; 24845976; 46506280; 24896975; 24885291; 24860081
• PubChem CID: 444235; 1390
• CHEBI ID: 113454
• CHEMBL: 543
• Chemspider ID: 1348
• Wikipedia Title: 1-Methylimidazole

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.4576601
• LogD (pH = 7.4): 0.0057640853
• Log P: 0.07845186
• Molar Refractivity: 23.9095 cm^3
• Polarizability: 8.900744 Å^3
• Polar Surface Area: 17.82 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.47
• LOG S: -1.72
• Solubility (Water): 2.26e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1000 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Oil
• Melting Point: -6 °C; -6 °C(lit.); -6°C; -6°C; -60°C
• Boiling Point: 195-197°C; 198 °C; 198 °C(lit.); 198°C
• Flash Point: 1.4 °F; -14 °C; -17 °C; 197.6 °F; 6.8 °F; 92 °C; 92°C; 92°C(197°F)
• Auto Ignition Point: 977 °F
• Density: 1.03; 1.03 g/cm3; 1.03 g/ml; 1.03 g/mL at 25 °C(lit.); 1.031
• Refractive Index: 1.4970; n20/D 1.379; n20/D 1.418; n20/D 1.429; n20/D 1.495(lit.); n20/D 1.497
• Vapor Pressure: 0.4 mmHg ( 20 °C)
• Hydrophobicity(logP): -0.06 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: 2-8°C, Desiccate, Store Under Nitrogen, Protect from light, AND WATER; Refrigerator
• Storage Warning: Corrosive/Harmful/Hygroscopic/Store under Argon; Hygroscopic
• RTECS: NI7000000
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: 2735; 2924; 3267; UN2922
• German water hazard class: 1; 2; 3
• Hazard Class: 3; 8
• Packing Group: 2; II; III
• Australian Hazchem: 3X
• Risk Statements: 11-19-20/21/22-34-37; 11-19-34-37; 11-20/21/22-34; 21/22-34; R:21/22-34
• Safety Statements: 1/2-26-36-45; 16-26-36/37/39-45; 26-36-45; S:26-36-45
• EU Classification: C7
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• Explode Limits: 15.7 %
• GHS Hazard statements: H225-H314-H335; H302-H312-H314; H314-H302-H312-H227
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P280-P305 + P351 + P338-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US); Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2; UN 3267 8/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.

Product Information

• Purity: ≥99%; ≥99.0% (GC); 95+%; 97%; 99%
• Grade: for oligonucleotide synthesis; puriss.; ReagentPlus®
• Impurities: <0.005% water; <0.01% water; ≤0.01% water
• Purified By: redistillation
• Quality Level: PREMIUM
• Quality: filtered through a 1μm filter
• Empirical Formula (Hill Notation): C4H6N2

DETAILS

MP Biomedicals - 02151655

Purity: 99% 1 ml = approx. 1.03 g A catalyst for mild acetylation of hydroxy compounds.

DrugBank - DB02671

Drug information: experimental

Sigma Aldrich - M50834

Packaging
100, 500 g in glass bottle
3 kg in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 336092

Packaging
1, 2 L in Sure/Seal™
View returnable container options.
100 mL in Sure/Seal™
200 L in Pure-Pac™ 1

Sigma Aldrich - 73267

Application
Reagent used in the phosphite triester method of oligonucleotide synthesis for the capping of the remaining free 5′-hydroxylgroups by acetylation. Reagent is suitable for use on ABI, Beckmann synthesizers.

Sigma Aldrich - 15628

Application
Reagent used in the phosphite triester method of oligonucleotide synthesis for the capping of the remaining free 5’-hydroxyl groups by acetylation. Reagent is suitable for use on Biosearch 8000, Expedite, Cyclone synthesizers.

Sigma Aldrich - 06849

Application
1-Methylimidazole has been used in a study to elaborate on the use of differential scanning calorimetry as a new indirect method for determination of vaporization enthalpies. 1-Methylimidazole has also been used in a study that analyzed the base content in in-service oils by Fourier Transform Infrared Spectroscopy.

Sigma Aldrich - 67560

Other Notes
Catalyst for the mild analytical acetylation of hydroxy compounds1,2

Sigma Aldrich - 28881

Application
Reagent used in the phosphite triester method of oligonucleotide synthesis for the capping of the remaining free 5’-hydroxyl groups by acetylation. Reagent is suitable for use on Milligen 7500 synthesizers.

Toronto Research Chemicals - M312980

A metabolite of 1-methyl-2-thioimidazole (methimazole). It inhibits bone resorption.

REFERENCES

• Dee, L.A., et al., Anal. Chem., 52: 572 (1980).
• Paterson, J.R., et al.: Biochem. Biophys. Res. Comm., 116, 449 (1983)
• Taurog, A., et al.: Endocrinology, 124, 30 (1989).
• Useful base for peptide coupling, etc. See, e.g.: J. Chem. Soc., Chem. Commun., 2223 (1995). For peptide reagents, see Appendix 6.
• Undergoes lithiation at the 2-position. Reaction of the Li derivative with ketones followed by dehydration with acetic anhydride is a good route to 2-alkylideneimidazoles: Synthesis, 78 (1990). Likewise, reaction with benzonitrile gives the 2-benzoyl derivative, the carbonyl group of which undergoes Wittig methylenation: Synth. Commun., 20, 321 (1990).
• Reacts with acid chlorides, including chloroformates, to give N-acylimidazolium salts, which are useful reagents for the acylation of, for example, amino acids: Bull. Soc. Chim. Fr., 1021 (1973).