23785-22-0

Basic information

• Product Name: 4-(Chloromethyl)-1H-imidazole
• Synonyms: 4-(CHLOROMETHYL)-1H-IMIDAZOLE HCL;4-(Chloromethyl)-1H-imidazole;4-(chloromethyl)-1H-imidazole(SALTDATA: HCl)
• CAS NO: 23785-22-0
• Molecular Formula: C₄H₅ClN₂
• Molecular Weight: 116.55
• Product Categories: Imidaxoles
• Mol File: 23785-22-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 328.761 °C at 760 mmHg
• Flash Point: 182.63 °C
• Appearance: /
• Density: 1.314 g/cm³
• Vapor Pressure: 0.000355mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• PKA: 13.04±0.10(Predicted)
• CAS DataBase Reference: 4-(Chloromethyl)-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Chloromethyl)-1H-imidazole(23785-22-0)
• EPA Substance Registry System: 4-(Chloromethyl)-1H-imidazole(23785-22-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• Hazardous Substances Data: 23785-22-0(Hazardous Substances Data)

Usage

General Description

4-(Chloromethyl)-1H-imidazole is a chemical compound with the molecular formula C4H5ClN2. It is a heterocyclic organic compound that contains both an imidazole ring and a chloromethyl group, making it a halogenated imidazole. It is commonly used in organic synthesis and as a building block for the preparation of various pharmaceuticals and agrochemicals. It is also used in the production of antifungal agents, corrosion inhibitors, and anesthetics. Additionally, it exhibits antimicrobial properties and is used in the formulation of some commercial products for its biocidal activity. However, it is important to handle this compound with caution, as it is considered hazardous and may cause skin and eye irritation upon contact.

InChI:InChI=1/C4H5ClN2/c5-1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)

Upstream product

• 32673-41-9 4-hydroxymethyl-1H-imidazole hydrochloride 
• 6293-52-3 4⁽⁵⁾-hydroxymethylimidazole picrate 
• 822-55-9 1H-imidazole-5-methanol 
• 822-55-9 (1H-imidazol-4-yl)methanol 

Downstream Products

• 18502-05-1 2-(1H-imidazol-5-yl)acetonitrile 
• 81488-32-6 (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-(1H-imidazol-4-ylmethylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 81488-21-3 (5R,6R)-6-Ethyl-3-(1H-imidazol-4-ylmethylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 128972-19-0 3-(1H-Imidazol-4-yl)-2-(8-isobutyl-6-phenyl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-propionic acid ethyl ester 

Relevant articles and documents

SUBSTITUTED IMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted imidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

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.

THE CHEMICAL SIMULATION OF THE "ATP-IMIDAZOLE" CYCLE

The synthetic strategy inherent in the "ATP-Imidazole" cycle and centred around the vicinal disposition of -NH2 and -CONH2 functions, has been demonstrated with anthranilamide (2) and 1-benzyl-5-aminoimidazole-4-carboxamide (1) as regeneratable carriers involving specifically N-alkylated quinazolin-4-ones, hypoxantines and adenines, as key intermediates.The isolation and characterization of the enamine (22) coupled with other observations has made it possible to rationalize the pathways involved in these cyclic operations.The practical utility of the synthetic strategy using regeneratable carriers has beem illustrated with the synthesis of a range of 1,5-disubstituted imidazoles.Whilst pathways leading to specific N-alkylation in the Natural cycle and in simulation studies are comparable, the subsequent events take place in a reverse order, primarily because of the divergence in the hydrolitic profile of the alkylated substrates.The action of dilute alkali on 3-alkylated quinazolin-4-ones leads to 2-3 rather than 3-4 bond rupture.Endeavours to promote the latter path, by blocking the 2 position gave unexpected results. 2-Methyl-3-phenacyl quinazolin-4-one gave with dilute alkali the novel aromatic tricyclic system (32) from trans-annular cyclization.On the other hand the 2-blocked 3-benzamido quinazolin-4-ones (33) and (34) gave triazoles (35) and (36) arising from the desired 3-4 rupture followed by cyclization initiated by the resulting amidine unit. 2-Phenil-3-benzamidoquinazolin-4-one (34) with distilled water at 200 deg C gave a number of products whicc have been identified and their formation explained.