2-Methylimidazole

• CAS: 693-98-1
• Catalog Number: ACM693981
• Category: Imidazoles
• Molecular Weight: 82.11
• Molecular Formula: C4H6N2
• Description: DryPowder; OtherSolid
• Synonyms: 2-Methylglyoxaline
• IUPAC Name: 2-methyl-1H-imidazole
• Canonical SMILES: CC1=NC=CN1
• InChI: 1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)
• InChI Key: LXBGSDVWAMZHDD-UHFFFAOYSA-N
• Boiling Point: 267.0 °C;267 °C
• Melting Point: 144 °C
• Density: 1.062 g/cm³
• Solubility: Very soluble in ethanol;In water, 8.09X10+4 mg/L at 25 °C (est)
• Appearance: White to Almost white powder to crystal
• Application: 2-Methylimidazole serves multiple important functions in various fields. It is primarily used as a raw material in the production of nitroimidazole antibiotics, which are effective against anaerobic bacterial and parasitic infections. In the realm of coordination chemistry, it acts as a ligand. The compound also plays a significant role in the industrial sector, serving as a hardener or accelerator for epoxy resins and aiding as an auxiliary agent for textile dyes. Additionally, 2-methylimidazole is employed as a catalyst in the refolding of enhanced colored fluorescent proteins. It provides a foundational building block for the synthesis of biologically active compounds and is utilized as an intermediate in the production of active pharmaceutical ingredients, including metronidazole and dimetridazole.
• Storage: Store under inert gas, 2-8℃
• Color/Form: Solid
• Complexity: 44.8
• Condition To Avoid: Air Sensitive
• Covalently-Bonded Unit Count: 1
• EC Number: 211-765-7
• Exact Mass: 82.053098g/mol
• Formal Charge: 0
• Hazard Statements: H302 : Harmful if swallowed.H314 : Causes severe skin burns and eye damage.H360 : May damage fertility or the unborn child.H371 : May cause damage to organs.H373 : May cause damage to organs through prolonged or repeated exposure.H341 : Suspected of causing genetic defects.H351 : Suspected of causing cancer.
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Heavy Atom Count: 6
• LogP: 0.24 (LogP);log Kow = 0.24
• MDL Number: MFCD00005190
• Monoisotopic Mass: 82.053098g/mol
• NSC Number: 21394
• Other Experimental: Henry's Law constant = 4.14X10-6 atm-cu m/mol at 25 °C (est);Hydroxyl radical reaction rate constant = 9.41X10-11 cu cm/molec-sec at 25 °C (est)
• Precautionary Statements: P501 : Dispose of contents/ container to an approved waste disposal plant.P260 : Do not breathe dust/ fume/ gas/ mist/ vapors/ spray.P270 : Do not eat, drink or smoke when using this product.P202 : Do not handle until all safety precautions have been read and understood.P201 : Obtain special instructions before use.P264 : Wash skin thoroughly after handling.P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.P308 + P313 : IF exposed or concerned: Get medical advice/ attention.P308 + P311 : IF exposed or concerned: Call a POISON CENTER/doctor.P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower.P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.P363 : Wash contaminated clothing before reuse.P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.P405 : Store locked up.
• Refractive Index: 1.62
• Rotatable Bond Count: 0
• Signal Word: Danger
• Specific Gravity: 1.16
• UNII: T0049Z45LZ
• Vapor Pressure: 6.9X10-4 mm Hg at 25 °C (est)
• XLogP3: 0.2

Synthetic Use

Upstream Synthesis Route 1

• 930-61-0
• 67-66-3

• 5053-43-0
• 95-58-9
• 693-98-1
• 930-62-1

Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435

Upstream Synthesis Route 2

• 930-61-0
• 67-66-3

• 5053-43-0
• 4994-86-9
• 693-98-1
• 930-62-1

Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435

Upstream Synthesis Route 3

• 930-61-0
• 67-66-3

• 4994-86-9
• 693-98-1
• 930-62-1
• 75712-73-1

Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435

Upstream Synthesis Route 4

• 23012-17-1

• 693-98-1

Reference: [1]Journal of the Chemical Society,1947,p. 96,100

Upstream Synthesis Route 5

• 13750-62-4

• 693-98-1

Reference: [1]Tetrahedron Letters,2015,vol. 56,p. 2688 - 2690
[2]Tetrahedron Letters,2002,vol. 43,p. 399 - 402
[3]Journal of the American Chemical Society,1949,vol. 71,p. 383,384

Upstream Synthesis Route 6

• 110-85-0

• 288-32-4
• 290-37-9
• 616-47-7
• 109-08-0
• 13925-00-3
• 693-98-1

Reference: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1990,vol. 39,p. 1340 - 1345
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1990,p. 1483 - 1488