4-p-Tolyl-1H-imidazole

Base Information

• Chemical Name: 4-p-Tolyl-1H-imidazole
• CAS No.: 670-91-7
• Molecular Formula: C10H10N2
• Molecular Weight: 158.203
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID90371711
• Nikkaji Number: J109.524B
• Wikidata: Q82159144
• Mol file: 670-91-7.mol

Synonyms:670-91-7;4-p-Tolyl-1H-imidazole;4-(4-methylphenyl)imidazole;4-(p-Tolyl)-1H-imidazole;4-(4-methylphenyl)-1H-imidazole;5-(4-methylphenyl)-1H-imidazole;5-(p-tolyl)imidazole;Imidazole, 4-p-tolyl-;SCHEMBL872238;DTXSID90371711;CYGFZUOECZAJFD-UHFFFAOYSA-N;4-(4-Methylphenyl)imidazole, tech;MFCD00832843;1H-Imidazole, 4-(4-methylphenyl)-;AKOS015951133;FT-0692623

Chemical Property of 4-p-Tolyl-1H-imidazole

Chemical Property:

• Melting Point: 98-102°C
• Boiling Point: 379.9 °C at 760 mmHg
• Flash Point: 206.8 °C
• PSA: 28.68000
• Density: 1.109 g/cm³
• LogP: 2.38510
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 158.084398327
• Heavy Atom Count: 12
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

4-p-Tolyl-1H-imidazole 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2=CN=CN2

Technology Process of 4-p-Tolyl-1H-imidazole

There total 5 articles about 4-p-Tolyl-1H-imidazole 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: 97.0%

1-benzyl-5-(4-tolyl)-1H-imidazole (1041845-39-9) → 4(5)-(4-tolyl)-1H-imidazole (670-91-7)

Guidance literature:

With HC(O)ONH₄; palladium dihydroxide; In methanol; for 2h; Heating;

DOI:10.1016/j.tet.2008.01.051

Reference yield: 28.0%

benzaldehyde dimethyl acetal (1125-88-8) + 4-(4-bromophenyl)-1H-imidazole (13569-96-5) → 4-(p-tolyl)-1H-imidazole (670-91-7)

Guidance literature:

With nickel(II) bromide dimethoxyethane; potassium phosphate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; In acetonitrile; benzene; for 24h; Glovebox; Sealed tube; Irradiation;

DOI:10.1021/jacs.1c12203

Reference yield: 24.0%

formamide (77287-34-4,77287-35-5,60100-09-6) + 4-(bromoacetyl)toluene (619-41-0) → 4-(p-tolyl)-1H-imidazole (670-91-7)

Guidance literature:

at 160 ℃; for 24h;

DOI:10.1002/anie.201813381

upstream raw materials:

formaldehyd

2-oxo-2-(4-tolyl)ethyl acetate

1-benzyl-5-(4-tolyl)-1H-imidazole

formamide

Downstream raw materials:

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

6-bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazine

Refernces

• 1、 Wang, Haiyang,Guo, Chang. "Enantioselective γ-Addition of Pyrazole and Imidazole Heterocycles to Allenoates Catalyzed by Chiral Phosphine". supporting information. p. 2854 - 2858. Retrieved 2019/02/14.
• 2、 Bellina, Fabio,Cauteruccio, Silvia,Di Fiore, Annarita,Marchetti, Chiara,Rossi, Renzo. "Highly selective synthesis of 4(5)-aryl-, 2,4(5)-diaryl-, and 4,5-diaryl-1H-imidazoles via Pd-catalyzed direct C-5 arylation of 1-benzyl-1H-imidazole". . p. 6060 - 6072. Retrieved 2008/12/20.