4'-(Imidazol-1-yl)acetophenone

Base Information

• Chemical Name: 4'-(Imidazol-1-yl)acetophenone
• CAS No.: 10041-06-2
• Molecular Formula: C11H10N2O
• Molecular Weight: 186.213
• Hs Code.: 29332990
• European Community (EC) Number: 233-123-5
• UNII: KQU6ES7DSS
• DSSTox Substance ID: DTXSID50143259
• Nikkaji Number: J241.241A
• Wikidata: Q72482343
• Pharos Ligand ID: MJ1968ZLVNGH
• ChEMBL ID: CHEMBL528463
• Mol file: 10041-06-2.mol

Synonyms:4'-(1-H-imidazole-1-yl)acetophenone;Ro 22-3581

Chemical Property of 4'-(Imidazol-1-yl)acetophenone

Chemical Property:

• Appearance/Colour: white to yellow powder
• Melting Point: 108-110 °C(lit.)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 360.873 °C at 760 mmHg
• PKA: 4.99±0.10(Predicted)
• Flash Point: 172.05 °C
• PSA: 34.89000
• Density: 1.132 g/cm³
• LogP: 2.07490
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 186.079312947
• Heavy Atom Count: 14
• Complexity: 209

Purity/Quality:

97% ^*data from raw suppliers

4''-(Imidazol-1-yl)acetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(C=C1)N2C=CN=C2
• Uses: 4′-(Imidazol-1-yl)acetophenone was used in the synthesis of (R)-(+)-4′-(imidozol-1-yl)-phenyl ethanol using spiroborate catalyst.

Technology Process of 4'-(Imidazol-1-yl)acetophenone

There total 15 articles about 4'-(Imidazol-1-yl)acetophenone 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: 100.0%

1H-imidazole (288-32-4) + para-bromoacetophenone (99-90-1) → 4'-(imidazol-1-yl)acetophenone (10041-06-2)

Guidance literature:

With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride; at 140 - 145 ℃; for 24h;

DOI:10.1055/s-2008-1067014

Reference yield: 99.0%

1H-imidazole (288-32-4) + para-chloroacetophenone (99-91-2) → 4'-(imidazol-1-yl)acetophenone (10041-06-2)

Guidance literature:

With copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; at 20 - 110 ℃;

DOI:10.1021/jo901462g

Reference yield: 99.0%

1H-imidazole (288-32-4) + 4-Iodoacetophenone (13329-40-3) → 4'-(imidazol-1-yl)acetophenone (10041-06-2)

Guidance literature:

With copper(II) acetate monohydrate; caesium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.025

upstream raw materials:

1H-imidazole

1-(4-fluorophenyl)ethanone

para-chloroacetophenone

para-bromoacetophenone

Downstream raw materials:

hydroxy<2-<4-(1H-imidazol-1-yl)phenyl>-2-oxoethyl>propanedioic acid diethyl ester

6-<4-(1H-imidazole-1-yl)phenyl>-3(2H)-pyridazinone

4-(1H-imidazol-1-yl)-β-oxobenzenepropanoic acid methyl ester

Refernces

• 1、 Hruszkewycz, Damian P.,Miles, Kelsey C.,Thiel,Stahl, Shannon S.. "Co/NHPI-mediated aerobic oxygenation of benzylic C-H bonds in pharmaceutically relevant molecules". . p. 1282 - 1287. Retrieved 2017.
• 2、 Ibrahim, Hany S.,Albakri, Mohamed E.,Mahmoud, Walaa R.,Allam, Heba Abdelrasheed,Reda, Ahmed M.,Abdel-Aziz, Hatem A.. "Synthesis and biological evaluation of some novel thiobenzimidazole derivatives as anti-renal cancer agents through inhibition of c-MET kinase". . p. 337 - 348. Retrieved 2019.
• 3、 Truong, Thanh,Nguyen, Chi V.,Truong, Ngoc T.,Phan, Nam T. S.. "Ligand-free N-arylation of heterocycles using metal-organic framework [Cu(INA)2] as an efficient heterogeneous catalyst". . p. 107547 - 107556. Retrieved 2015.
• 4、 Liu, Yashuai,Gu, Ningning,Liu, Ping,Xie, Jianwei,Dai, Bin,Liu, Yan. "A simple and efficient 2N2O-Cu(II) complex as a catalyst for N-arylation of imidazoles in water". . p. 468 - 470. Retrieved 2015.
• 5、 Venkateswarlu, Katta,Rao, Kanusu Umamaheswara. "Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan–Lam coupling in water". . . Retrieved 2021/03/03.
• 6、 Wu, Fengtian,Li, Huiqin,Xie, Jianwei. "Copper quinolate: A simple and efficient catalytic complex for coupling reactions". . . Retrieved 2019/11/22.