4-Hydroxystilbene

Base Information

• Chemical Name: 4-Hydroxystilbene
• CAS No.: 6554-98-9
• Molecular Formula: C14H12O
• Molecular Weight: 196.249
• Hs Code.: 29071990
• European Community (EC) Number: 223-328-8,229-483-8
• NSC Number: 48625,43309
• UNII: S6E4ZX5JSS
• DSSTox Substance ID: DTXSID2022464
• Nikkaji Number: J145.987B,J217.708K
• Wikidata: Q27116417
• Metabolomics Workbench ID: 27965
• ChEMBL ID: CHEMBL195624
• Mol file: 6554-98-9.mol

Synonyms:4-hydroxy-trans-stilbene;4-hydroxystilbene;4-hydroxystilbene, (E)-isomer;4-stilbenol

Chemical Property of 4-Hydroxystilbene

Chemical Property:

• Appearance/Colour: Yellow to light brown crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 185-189oC
• Refractive Index: 1.4700 (estimate)
• Boiling Point: 336.4°Cat760mmHg
• PKA: 9.59±0.13(Predicted)
• Flash Point: 161.1°C
• PSA: 20.23000
• Density: 1.147g/cm³
• LogP: 3.56260
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 196.088815002
• Heavy Atom Count: 15
• Complexity: 195

Purity/Quality:

99%, ^*data from raw suppliers

TRANS-4-HYDROXYSTILBENE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-Hydroxystilbene

There total 103 articles about 4-Hydroxystilbene 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%

4-(2-phenylethynyl)phenol (1849-26-9) → trans-4-Hydroxystilbene (6554-98-9)

Guidance literature:

With formic acid; (1,2-dimethoxyethane)dichloronickel(II); zinc; bis(2-diphenylphosphinoethyl)phenylphosphine; In 1,4-dioxane; at 120 ℃; for 16h; stereoselective reaction; Sealed tube;

DOI:10.1021/acs.joc.5b01047

Reference yield: 98.0%

benzenediazonium tetrafluoroborate (369-57-3) + 4-Vinylphenol (2628-17-3,24979-70-2) → trans-4-Hydroxystilbene (6554-98-9)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl acetamide; at 20 ℃; for 1.5h; optical yield given as %de; stereoselective reaction;

DOI:10.1021/ja203164p

Reference yield: 96.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 4-hydroxybenzenediazonium tetrafluoroborate → trans-4-Hydroxystilbene (6554-98-9)

Guidance literature:

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

DOI:10.1039/c3ob40420j

upstream raw materials:

ethylmagnesium iodide

E-1-(phenyl)-2-(4'-methoxyphenyl)ethene

benzyltriphenylphosphonium chloride

4-hydroxy-benzaldehyde

Downstream raw materials:

diethyl-[2-(trans-stilbenyl-⁽⁴⁾-oxy)-ethyl]-amine

trans-stilben-4-yloxy-acetonitrile

dibutyl-(3-trans-stilben-4-yloxy-propyl)-amine

(Z)-1-(4-hydroxyphenyl)-2-phenylethene

Refernces

• 1、 Kashid, Abhijit A.,Patil, Dharmaraj J.,Mali, Ramling D.,Patil, Vijay P.,Neethu,Meroliya, Heena K.,Waghmode, Shobha A.,Iyer, Suresh. "Bimetallic Ni–Pd Synergism—Mixed Metal Catalysis of the Mizoroki-Heck Reaction and the Suzuki–Miyaura Coupling of Aryl Bromides". . p. 353 - 358. Retrieved 2020/08/05.
• 2、 Akiyama, Toshiki,Arisawa, Mitsuhiro,Haneoka, Hitoshi,Harada, Kazuo,Hasegawa, Jun-Ya,Honma, Tetsuo,Mashima, Kazushi,Sato, Yoshihiro,Shimoda, Shuhei,Shio, Yasunori,Suzuki, Takeyuki,Tamenori, Yusuke,Tsurugi, Hayato,Tsuruta, Kazuki,Wada, Yuki,Yamada, Makito. "Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon-Carbon/Carbon-Nitrogen Bond-Forming Reactions". supporting information. p. 7244 - 7249. Retrieved 2020/10/12.