4-[(E)-2-(4-Chlorophenyl)ethenyl]phenol

Base Information

• Chemical Name: 4-[(E)-2-(4-Chlorophenyl)ethenyl]phenol
• CAS No.: 18951-46-7
• Molecular Formula: C14H11ClO
• Molecular Weight: 230.694
• NSC Number: 11155
• Nikkaji Number: J303.855F,J3.148.996B
• ChEMBL ID: CHEMBL4218424
• Mol file: 18951-46-7.mol

Synonyms:4-Stilbenol, 4'-chloro-, (E)-;C14H11ClO;18951-46-7;4-[(E)-2-(4-Chlorophenyl)ethenyl]phenol;NSC11155;6280-47-3;4'-Chlorostilbene-4-ol;(E)-4'-Chlorostilbene-4-ol;SCHEMBL8395184;CHEMBL4218424;4-Chloro-4'-hydroxy-E-stilbene;MYQBBEYFTBZYRE-OWOJBTEDSA-N;NSC-11155;4-[(E)-2-(4-chlorophenyl)vinyl]phenol;4-[(E)-2-(4-Chlorophenyl)ethenyl]phenol #;Phenol, 4-[(E)-2-(4-chlorophenyl)ethenyl]-

Chemical Property of 4-[(E)-2-(4-Chlorophenyl)ethenyl]phenol

Chemical Property:

• Vapor Pressure: 4.61E-06mmHg at 25°C
• Boiling Point: 372.1°C at 760 mmHg
• Flash Point: 178.8°C
• Density: 1.26g/cm³
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 230.0498427
• Heavy Atom Count: 16
• Complexity: 223

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC2=CC=C(C=C2)Cl)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C2=CC=C(C=C2)Cl)O

Technology Process of 4-[(E)-2-(4-Chlorophenyl)ethenyl]phenol

There total 14 articles about 4-[(E)-2-(4-Chlorophenyl)ethenyl]phenol 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-vinylbenzyl chloride (1073-67-2,24991-47-7) + 4-hydroxybenzenediazonium tetrafluoroborate → (E)-4-<2-(4-chlorophenyl)ethenyl>phenol (18951-46-7)

Guidance literature:

With sodium acetate; palladium diacetate; In methanol; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c3ob40420j

Reference yield: 81.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) + 4-Vinylphenol (2628-17-3,24979-70-2) → (E)-4-<2-(4-chlorophenyl)ethenyl>phenol (18951-46-7)

Guidance literature:

4-Vinylphenol; With caesium carbonate; sodium iodide; Merrifield resin; In N,N-dimethyl-formamide; at 80 ℃; for 12h;

4-vinylbenzyl chloride; RuCl₂(=CHPh)[1,3-ImH₂]P(Cy)3; In benzene; at 80 ℃; for 12h;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(02)01528-9

Reference yield: 70.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) + 4-bromo-phenol (106-41-2) → (E)-4-<2-(4-chlorophenyl)ethenyl>phenol (18951-46-7)

Guidance literature:

With [PdBr₂(PPh₃)2]; potassium carbonate; In N,N-dimethyl-formamide; at 20 - 100 ℃; for 8h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.08.120

upstream raw materials:

4-chlorophenylacetic Acid

4-hydroxy-benzaldehyde

p-Coumaric Acid

4-chloro-aniline

Downstream raw materials:

C₁₉H₂₀BrClO

{4-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenoxy}-acetic acid ethyl ester

C₂₈H₂₀Cl₂O₂

N-(4-chlorobenzyl)-4-methoxyaniline

Refernces

• 1、 Peng, Yi,Fan, Yan-Hui,Li, Si-Yuan,Li, Bin,Xue, Jing,Deng, Qing-Hai. "Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage". supporting information. p. 8389 - 8394. Retrieved 2019/10/16.
• 2、 De Filippis, Barbara,Agamennone, Mariangela,Ammazzalorso, Alessandra,Bruno, Isabella,D'Angelo, Alessandra,Di Matteo, Mauro,Fantacuzzi, Marialuigia,Giampietro, Letizia,Giancristofaro, Antonella,MacCallini, Cristina,Amoroso, Rosa. "PPARα agonists based on stilbene and its bioisosteres: Biological evaluation and docking studies". supporting information. p. 1513 - 1517. Retrieved 2015/08/18.