45533-87-7

Basic information

• Product Name: 4-(Hydroxymethyl)-2-methyl-1H-imidazole
• Synonyms: 4-(Hydroxymethyl)-2-methyl-1H-imidazole;(2-Methyl-1H-iMidazol-5-yl)Methanol;1H-IMidazole-4-Methanol, 2-Methyl-;2-methyl-1H-imidazole-5-methanol;2-methyl-4-hydroxymethylimidazole;(2-Methyl-1H-imidazol-4-yl)
• CAS NO: 45533-87-7
• Molecular Formula: C5H8N2O
• Molecular Weight: 112.12982
• Mol File: 45533-87-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 120-122
• Boiling Point: 392.5 °C at 760 mmHg
• Flash Point: 191.1 °C
• Appearance: /
• Density: 1.231g/cm³
• Vapor Pressure: 7.3E-07mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(Hydroxymethyl)-2-methyl-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Hydroxymethyl)-2-methyl-1H-imidazole(45533-87-7)
• EPA Substance Registry System: 4-(Hydroxymethyl)-2-methyl-1H-imidazole(45533-87-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 45533-87-7(Hazardous Substances Data)

Usage

General Description

4-(Hydroxymethyl)-2-methyl-1H-imidazole, also known as Clonidine Impurity A, is a chemical compound with the molecular formula C5H8N2O that is commonly used as an intermediate in the synthesis of pharmaceuticals. It is a derivative of imidazole and contains a hydroxymethyl and a methyl group attached to the imidazole ring. 4-(Hydroxymethyl)-2-methyl-1H-imidazole is often used in the manufacturing of medicines such as clonidine, an antihypertensive medication, and is important for the pharmaceutical industry. Its chemical structure and properties make it a valuable building block in the production of various drugs, and it plays a crucial role in the development and production of pharmaceutical products.

InChI:InChI=1/C5H8N2O/c1-4-6-2-5(3-8)7-4/h2,8H,3H2,1H3,(H,6,7)

Upstream product

• 96-26-4 dihydroxyacetone 
• 124-42-5 acetamidine hydrochloride 
• 75-07-0 acetaldehyde 
• 143-37-3 acetamidine 
• 14777-27-6 methyl acetimidate hydrochloride 
• 2208-07-3 ethyl acetimidate hydrochloride 
• 35034-22-1 2-methylimidazole-4⁽⁵⁾-carbaldehyde 
• 638-14-2 2,4,6-trimethyl-[1,3,5]triazinane 
• 6347-01-9 fructopyranose 
• 57-48-7 D-Fructose 

Downstream Products

• 59022-78-5 4(5)-(chloromethyl)-2-methylimidazole hydrochloride 
• 59022-79-6 (2-methyl-1(3)H-imidazol-4-yl)-acetonitrile 
• 59022-79-6 4(5)-(cyanomethyl)-2-methylimidazole 

Relevant articles and documents

MECHANISTIC STUDIES OF THE UROCANASE REACTION USING (1)H- AND (31)P-NMR SPECTROSCOPY AND THE SUBSTRATE ANALOGUE 2-METHYLUROCANATE

The reaction of 2-methylurocanate with urocanase from Pseudomonas putida was monitored by (1)H-NMR spectroscopy at 500 MHz.The following conclusions were drawn: (i) 2-methylurocanate reacts 128 times more slowly with urocanase than does urocanate, (ii) no signals for the enol form of the produced 2-methylimidazolone propionate were detected, (iii) 2-methylimidazolone propionate is about 25 times more stable to hydrolysis than imidazolone propionate, (iv) the urocanase-catalysed exchange of the 5-proton of 2-methylurocanate with the solvent deuterium is 1.3 times faster than the overall reaction and (v) the non-enzymic exchange of the Me protons of 2-methylimidazolone propionate with solvent D takes place with a half life of 5.8 hr. By (1)H-NMR spectroscopy it was shown that the urocanase reaction is reversible.At 8o and pD 6.3 1.6percent of the total imidazolone propionate was converted into urocanate. Apart from the pyrophosphate ester group of NAD(1+) no phosphorylated groups could be detected in urocanase by (31)P-NMR spectroscopy.

5-Substituted imidazole-4-acetic acid analogues: Synthesis, modeling, and pharmacological characterization of a series of novel γ-aminobutyric acidC receptor agonists

A series of ring-substituted analogues of imidazole-4-acetic acid (IAA, 4), a partial agonist at both GABAA and GABAC receptors (GABA = γ-aminobutyric acid), have been synthesized. The synthesized compounds 8a-1 have been evaluated a

Highly potent geminal bisphosphonates. From pamidronate disodium (Aredia) to zoledronic acid (Zometa)

Bisphosphonates (BPs) are pyrophosphate analogues in which the oxygen in P-O-P has been replaced by a carbon, resulting in a metabolically stable P-C-P structure. Pamidronate (1b, Novartis), a second-generation BP, was the starting point for extensive SAR studies. Small changes of the structure of pamidronate lead to marked improvements of the inhibition of osteoclastic resorption potency. Alendronate (1c, MSD), with an extra methylene group in the N-alkyl chain, and olpadronate (1h, Gador), the N,N-dimethyl analogue, are about 10 times more potent than pamidronate. Extending one of the N-methyl groups of olpadronate to a pentyl substituent leads to ibandronate (1k, Roche, Boehringer-Mannheim), which is the most potent close analogue of pamidronate. Even slightly better antiresorptive potency is achieved with derivatives having a phenyl group linked via a short aliphatic tether of three to four atoms to nitrogen, the second substituent being preferentially a methyl group (e.g., 4g, 4j, 5d, or 5r). The most potent BPs are found in the series containing a heteroaromatic moiety (with at least one nitrogen atom), which is linked via a single methylene group to the geminal bisphosphonate unit. Zoledronic acid (6i), the most potent derivative, has an ED50 of 0.07 mg/kg in the TPTX in vivo assay after sc administration. It not only shows by far the highest therapeutic ratio when comparing resorption inhibition with undesired inhibition of bone mineralization but also exhibits superior renal tolerability. Zoledronic acid (6i) has thus been selected for clinical development under the registered trade name Zometa. The results of the clinical trials indicate that low doses are both efficacious and safe for the treatment of tumor-induced hypercalcemia, Paget's disease of bone, osteolytic metastases, and postmenopausal osteoporosis.