2-[4-(Hydroxymethyl)phenyl]benzonitrile

Base Information

• Chemical Name: 2-[4-(Hydroxymethyl)phenyl]benzonitrile
• CAS No.: 154709-19-0
• Molecular Formula: C14H11 N O
• Molecular Weight: 209.247
• DSSTox Substance ID: DTXSID20362718
• Nikkaji Number: J1.575.820A
• Wikidata: Q82146058
• Mol file: 154709-19-0.mol

Synonyms:154709-19-0;2-[4-(hydroxymethyl)phenyl]benzonitrile;4'-(HYDROXYMETHYL)-[1,1'-BIPHENYL]-2-CARBONITRILE;4'-hydroxymethyl-biphenyl-2-carbonitrile;4'-(HYDROXYMETHYL)BIPHENYL-2-CARBONITRILE;SCHEMBL1713;4-(2-Cyanophenylbenzyl alcohol;[1,1'-Biphenyl]-2-carbonitrile, 4'-(hydroxymethyl)-;2'-cyano-4-hydroxymethylbiphenyl;4-Hydroxymethyl-2'-cyanobiphenyl;DTXSID20362718;2'-Cyano-4-hydroxymethyl-biphenyl;MFCD01318462;C90687

Chemical Property of 2-[4-(Hydroxymethyl)phenyl]benzonitrile

Chemical Property:

• PSA: 44.02000
• LogP: 2.71758
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 209.084063974
• Heavy Atom Count: 16
• Complexity: 259

Purity/Quality:

99.90% ^*data from raw suppliers

2-[4-(Hydroxymethyl)phenyl]benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C#N)C2=CC=C(C=C2)CO
• Uses: 2-[4-(Hydroxymethyl)phenyl]benzonitrile is an impurity of 4’-Bromomethyl-2-cyanobiphenyl (B685335), which is used in protein-binding studies of quinoxaline angiotensin II receptor antagonists.

Technology Process of 2-[4-(Hydroxymethyl)phenyl]benzonitrile

There total 9 articles about 2-[4-(Hydroxymethyl)phenyl]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: 91.4%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + biphenyl-2-carbonitrile (24973-49-7) → 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carbonitrile (154709-19-0)

Guidance literature:

With hydrogenchloride; zinc(II) chloride; In 1,2-dimethoxyethane; water; at 0 - 5 ℃; Reagent/catalyst;

Reference yield: 76.0%

4-bromobenzenemethanol (873-75-6) + 2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzonitrile (214360-47-1) → 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carbonitrile (154709-19-0)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; toluene; at 100 ℃; for 5h;

DOI:10.1021/ol015598+

Reference yield:

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carbonitrile (154709-19-0)

Guidance literature:

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile; With potassium acetate; In water; toluene; at 90 ℃; for 12h;

With sodium hydroxide; In water; toluene; at 50 - 70 ℃; for 5h;

upstream raw materials:

4-bromobenzenemethanol

2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzonitrile

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

4-bromo-benzaldehyde

Downstream raw materials:

4'-hydroxymethyl-2-(N-trityl-1H-tetrazol-5-yl)biphenyl

N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole

2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-methanol

4-(2-Cyanophenyl)benzaldehyde

Refernces

• 1、 López-Rodríguez, Rocío,Ros, Abel,Fernández, Rosario,Lassaletta, José M.. "Pinacolborane as the boron source in nitrogen-directed borylations of aromatic N, N -dimethylhydrazones". . p. 9915 - 9920. Retrieved 2013/01/15.
• 2、 Kristensen, Jesper,Lysen, Morten,Vedso, Per,Begtrup, Mikael. "Synthesis of Ortho Substituted Arylboronic Esters by in Situ Trapping of Unstable Lithio Intermediates". . p. 1435 - 1437. Retrieved 2007/10/03.