Imidazole

• CAS: 288-32-4
• Catalog Number: ACM288324-3
• Category: Other Products
• Molecular Weight: 68.08
• Molecular Formula: C3H4N2
• Description: Imidazole is a biocompatible molecule that is used as a scaffold for biomimetic applications. It is used as a bioreagent with an ability to hydrogen bond with drugs and proteins. It can be also be used as an additive for the formation of an electrolyte for fuel cell applications.
• Synonyms: Glyoxaline
• IUPAC Name: 1H-imidazole
• Canonical SMILES: C1=CN=CN1
• InChI: InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
• InChI Key: RAXXELZNTBOGNW-UHFFFAOYSA-N
• Boiling Point: 256 °C
• Melting Point: 88-91 °C
• Flash Point: 145 °C - closed cup
• Density: Relative density (water = 1): 1.03
• Solubility: Very soluble in water;In water, 241 g/100 g at 20 deg C;In water, 2060 g/kg H₂O at 19 deg C;In water, 663 g/L at 20 deg C;Very soluble in ethanol; soluble in diethyl ether, acetone, pyridine; slightly soluble in benzene;Solubility in water, g/100ml at 20 °C: 63.3 (good)
• Appearance: Crystalline
• Application: Metal Plating, Electropolishing, Metal Reprocessing, Phase transfer media, Batteries Fuel Cells, Nanomaterials, Industrial Solvents, Nuclear Fuel Red Waste, Enzymatic Catalysis, Lubricants Heat Transfer and Solar Energy Conversion.
• Storage: Store below +30 °C
• Chemical Formula: IM
• Color/Form: Monoclinic prisms from benzene;Colorless crystals;Colorless-yellow solid
• Complexity: 28.1
• Condition To Avoid: Air Sensitive
• Covalently-Bonded Unit Count: 1
• Decomposition: Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx), hydrogen cyanide (hydrocyanic acid).;Decomposes on burning. This produces toxic fumes including nitrogen oxides.;When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
• EC Number: 206-019-2
• Exact Mass: 68.037448136
• Hazard Statements: H301 : Toxic if swallowed.H314 : Causes severe skin burns and eye damage.H361 : Suspected of damaging fertility or the unborn child.H371 : May cause damage to organs.
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Heavy Atom Count: 5
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 1
• ICSC Number: 1721
• MDL Number: MFCD00005183
• Monoisotopic Mass: 68.037448136
• NSC Number: 60522
• Octanol Water Partition Coefficient: -0.08 (LogP);log Kow = -0.08;-0.08;-0.02
• Odor: Amine-like odor
• Other Experimental: Density: 1.0303 g/cu m at 101 deg C;Index of refraction: 1.4801 at 101 deg C;Viscosity: 2.696 mPa sec at 100 deg C;Molar heat capacity Cp (gas) = 71.3 J/mol K;Enthalpy of formation (crystal) = 49.8 kJ/mol;Enthalpy of fusion = 12.96 kJ/mol;Enthalpy of vaporization (220-265 deg C) = 57.12 kJ/mol;log Kow = -0.02 at 25 deg C;Vapor pressure = 0.327 Pa at 25 deg C (2.25X10-2 mm Hg at 25 deg C);Henry's Law constant = 3.8X10-6 atm-cu m/mol at 25 deg C (est; for the neutral species);Hydroxyl radical reaction rate constant = 3.6X10-11 cu cm/mole-sec at 24 deg C
• pH: pH 10.5 for 38 g/L at 20 deg C
• Physical Description: OtherSolid;Solid;COLOURLESS-TO-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.
• 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 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. 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
• RTECS Number: NI3325000
• Signal Word: Danger
• Specific Gravity: 1.16
• Stability: Stable under recommended storage conditions.
• Topological Polar Surface Area: 28.7 Ų
• UNII: 7GBN705NH1
• UN Number: 3263
• Vapor Pressure: 4.4X10-2 mm Hg at 25 deg C (est);Vapor pressure, Pa at 20 °C: 0.3

Case Study

Synthesis of Multi-Substituted Imidazole Derivatives via Heterogeneous Catalysis

Kerru, Nagaraju, et al. Synthetic Communications, 2019, 49(19), 2437-2459.

The unique structural characteristics of the imidazole ring and the ideal electron-rich properties facilitate imidazole derivatives to easily bind to a variety of enzymes and receptors in biological systems through a variety of weak interactions, thereby exhibiting a wide range of biological activities. Many heterogeneous catalytic reaction pathways have been investigated for the synthesis of multisubstituted imidazole conjugates.
Heterogeneous catalytic synthesis of imidazole derivatives
· Effective heterogeneous catalytic materials include iron oxide, silicon dioxide, zirconia, chitosan, and aluminum oxide, etc.
· The Lewis acid iron oxide nanocomposites, zirconia, aluminum oxide, and nanoporous silica acid catalysts were applied in one-pot condensation reaction afforded multisubstituted imidazoles.
· Success of use of ionic liquid in construction of functionalized imidazoles opens new avenues of their synthesis.

Synthetic Use

Upstream Synthesis Route 1

• 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

Downstream Synthesis Route 1

• 288-32-4

• 2302-30-9
• 2034-22-2
• 2302-25-2

Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 95 - 99
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 95 - 99

Downstream Synthesis Route 2

• 288-32-4
• 77-48-5

• 2302-25-2
• 77-71-4

Reference: [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 2-3, p. 499 - 507

Downstream Synthesis Route 3

• 288-32-4

• 2302-25-2

Reference: [1] Oriental Journal of Chemistry, 2015, vol. 31, # 4, p. 2239 - 2245
[2] Oriental Journal of Chemistry, 2015, vol. 31, # 4, p. 2239 - 2245

Downstream Synthesis Route 4

• 288-32-4
• 106-94-5

• 35203-44-2

Reference: [1]Dalton Transactions,2013,vol. 42,p. 1385 - 1393

Downstream Synthesis Route 5

• 288-32-4
• 3314-30-5
• 122-52-1

• 78645-33-7
• 78645-31-5

Reference: [1]Journal of general chemistry of the USSR,1981,vol. 51,p. 636 - 638
Zhurnal Obshchei Khimii,1981,vol. 51,p. 775 - 778

* For details of the synthesis route, please refer to the original source to ensure accuracy.