1-Benzylimidazole

Base Information

• Chemical Name: 1-Benzylimidazole
• CAS No.: 4238-71-5
• Molecular Formula: C10H10N2
• Molecular Weight: 158.203
• Hs Code.: 29332900
• European Community (EC) Number: 224-200-4
• NSC Number: 126828,217337
• UNII: W4C9Z5BCV7
• DSSTox Substance ID: DTXSID60195183
• Nikkaji Number: J198H
• Wikidata: Q27095323
• Pharos Ligand ID: 9PQNSSY3QQHG
• Metabolomics Workbench ID: 149021
• ChEMBL ID: CHEMBL14192
• Mol file: 4238-71-5.mol

Synonyms:1-benzylimidazole;N-benzylimidazole

Chemical Property of 1-Benzylimidazole

Chemical Property:

• Appearance/Colour: Brownish crystals
• Vapor Pressure: 0.00112mmHg at 25°C
• Melting Point: 68-70 °C(lit.)
• Refractive Index: 1.579
• Boiling Point: 310 °C at 760 mmHg
• PKA: 6.79±0.10(Predicted)
• Flash Point: 141.3 °C
• PSA: 17.82000
• Density: 1.04 g/cm³
• LogP: 1.93140
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: insoluble
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 158.084398327
• Heavy Atom Count: 12
• Complexity: 130

Purity/Quality:

99% ^*data from raw suppliers

Benzylimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 36/37/38:
• Hazard Codes: 36/37/38:
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Imidazoles
• Canonical SMILES: C1=CC=C(C=C1)CN2C=CN=C2
• General Description: **1-Benzylimidazole** is an N-substituted imidazole derivative that serves as a reactant in benzyne-mediated tandem reactions, enabling the synthesis of aryl amines containing anthracene. It participates in a transition-metal-free process involving a Diels-Alder reaction followed by nucleophilic coupling, yielding anthracene-based aryl amines under mild conditions (50 °C, acetonitrile). This highlights its utility as a versatile intermediate for constructing complex aromatic frameworks relevant to natural products and functional materials.

Technology Process of 1-Benzylimidazole

There total 60 articles about 1-Benzylimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1H-imidazole (288-32-4) + benzyl chloride (100-44-7) → 1-benzylimidazole (4238-71-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 70 ℃; for 120h;

DOI:10.1002/pola.23763

Reference yield: 95.0%

benzoimidazole (51-17-2,79351-71-6) + benzyl chloride (100-44-7) → 1-benzylimidazole (4238-71-5)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; for 0.25h; Ambient temperature;

Reference yield: 84.0%

1-benzyl-3-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazolium bromide → 1-benzylimidazole (4238-71-5)

Guidance literature:

With hydrogenchloride; at 80 ℃; for 2h;

upstream raw materials:

1H-imidazole

benzyl chloride

1-benzyl-1H-imidazole-2-thione

benzyl bromide

Downstream raw materials:

3-benzyl-1-(2-picolyl)imidazolium iodide

1-benzyl-2-iodo-1H-imidazole

1-benzyl-2-diethylphosphonoimidazole

[MeHg(N-benzylimidazole)]NO₃

Refernces

A new tandem reaction of benzyne: One-pot synthesis of aryl amines containing anthracene

10.1021/ol063017g

The study investigates a novel tandem reaction involving benzyne and N-substituted imidazoles to synthesize aryl amines containing anthracene under mild conditions. Benzyne, generated from o-trimethylsilyl aryltriflates, reacts with various N-substituted imidazoles, such as N-methylimidazole, N-ethylimidazole, and N-benzylimidazole, to form aryl amines with anthracene in a one-pot process. The reaction is believed to proceed via a tandem mechanism involving a Diels-Alder reaction and an intermolecular nucleophilic coupling reaction. The ratio of benzyne to imidazole is crucial for the reaction direction, and the optimized conditions include a 1:1 ratio at 50 °C in acetonitrile solvent for 12 hours. The study provides a transition-metal-free method to construct aryl amines containing anthracene, which are important building blocks in natural products and functional materials.