4-(Phenoxymethyl)benzonitrile

Base Information

• Chemical Name: 4-(Phenoxymethyl)benzonitrile
• CAS No.: 57928-75-3
• Molecular Formula: C₁₄H₁₁NO
• Molecular Weight: 209.247
• DSSTox Substance ID: DTXSID70481145
• Nikkaji Number: J293.121D
• Wikidata: Q82316390
• Mol file: 57928-75-3.mol

Synonyms:4-(phenoxymethyl)benzonitrile;57928-75-3;SCHEMBL8618909;DTXSID70481145;AKOS000183259

Chemical Property of 4-(Phenoxymethyl)benzonitrile

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 209.084063974
• Heavy Atom Count: 16
• Complexity: 241

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OCC2=CC=C(C=C2)C#N

Technology Process of 4-(Phenoxymethyl)benzonitrile

There total 7 articles about 4-(Phenoxymethyl)benzonitrile 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: 98.0%

4-cyanobenzyl bromide (17201-43-3) + phenol (108-95-2,27073-41-2) → 4-(phenoxymethyl)benzonitrile (57928-75-3)

Guidance literature:

With potassium phosphate; tetrabutylammomium bromide; In water; at 20 ℃; for 2h; Sealed tube; Green chemistry;

DOI:10.1016/j.tet.2014.01.004

Reference yield: 94.0%

4-Cyanobenzyl alcohol (874-89-5) + triphenylsulfonium trifluoromethanesulfonate (66003-78-9,130595-32-3,220122-79-2) → 4-(phenoxymethyl)benzonitrile (57928-75-3)

Guidance literature:

With cesium hydroxide; In 1,4-dioxane; at 50 ℃; for 24h; Inert atmosphere; Glovebox;

DOI:10.1002/asia.201900968

Reference yield: 89.0%

4-cyanobenzyl bromide (17201-43-3) + phenylboronic acid (98-80-6) → 4-(phenoxymethyl)benzonitrile (57928-75-3)

Guidance literature:

With dihydrogen peroxide; palladium diacetate; sodium hydroxide; In water; at 80 ℃; for 10h; Reagent/catalyst; Temperature; Time; Catalytic behavior;

DOI:10.1016/j.catcom.2018.10.026

upstream raw materials:

sodium phenoxide

4-cyanobenzyl bromide

4-Cyanochlorobenzene

phenol

Downstream raw materials:

4-phenoxymethyl-benzoic acid

4-phenoxymethyl-benzylamine

4-((4-iodophenoxy)methyl)benzonitrile

4-(4-cyanobenzyloxy)bromobenzene

Refernces

• 1、 Ming, Xiao-Xia,Tian, Ze-Yu,Zhang, Cheng-Pan. "Base-Mediated O-Arylation of Alcohols and Phenols by Triarylsulfonium Triflates". supporting information. p. 3370 - 3379. Retrieved 2019/11/03.
• 2、 Molander, Gary A.,Canturk, Belgin. "Preparation of potassium alkoxymethyltrifluoroborates and their cross-coupling with aryl chlorides". supporting information; experimental part. p. 2135 - 2138. Retrieved 2009/05/26.