Triphenylethylene

Base Information

• Chemical Name: Triphenylethylene
• CAS No.: 58-72-0
• Molecular Formula: C20H16
• Molecular Weight: 256.347
• Hs Code.: 29029080
• European Community (EC) Number: 200-395-1
• NSC Number: 17535
• UNII: S4ZLZ1K74B
• DSSTox Substance ID: DTXSID3022320
• Nikkaji Number: J1.389G,J3.252.092H
• Wikipedia: Triphenylethylene
• Wikidata: Q25100760
• NCI Thesaurus Code: C29863
• Metabolomics Workbench ID: 67512
• ChEMBL ID: CHEMBL3115201
• Mol file: 58-72-0.mol

Synonyms:triphenylethylene

Chemical Property of Triphenylethylene

Chemical Property:

• Appearance/Colour: White to slightly beige powder
• Vapor Pressure: 5.34E-05mmHg at 25°C
• Melting Point: 68-71 °C
• Refractive Index: 1.645
• Boiling Point: 358.2 °C at 760 mmHg
• Flash Point: 165 °C
• PSA: 0.00000
• Density: 1.072 g/cm³
• LogP: 5.27550
• Storage Temp.: Store below +30°C.
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 256.125200510
• Heavy Atom Count: 20
• Complexity: 276

Purity/Quality:

99% ^*data from raw suppliers

Triphenylethylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N,Xi
• Statements: 22-36-50/53
• Safety Statements: 26-36/37-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: Triphenylethylene is used in preparation of Esterase activated aggregation-induced luminescent anticancer prodrug.

Technology Process of Triphenylethylene

There total 329 articles about Triphenylethylene 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: 96.0%

diphenyl acetylene (501-65-5) + phenylboronic acid (98-80-6) → Triphenylethylene (58-72-0)

Guidance literature:

With N,N-diisopropyl-1,1-diphenylphosphanamine; potassium carbonate; palladium dichloride; In tetrahydrofuran; at 20 - 65 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2010.01.086

Reference yield: 95.0%

benzophenone (119-61-9) + benzyltrimethylsilane (770-09-2) → Triphenylethylene (58-72-0)

Guidance literature:

benzyltrimethylsilane; With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; at -50 ℃; Inert atmosphere;

benzophenone; In tetrahydrofuran; hexane; at -50 - 20 ℃; Inert atmosphere;

DOI:10.1055/a-1493-6670

Reference yield: 93.0%

iodobenzene (591-50-4) + (E)-1,2-diphenyl-ethene (103-30-0) → Triphenylethylene (58-72-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 120 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.joc.5b01358

upstream raw materials:

pyridine

1-chloro-1,1,2-triphenyl-ethane

n-butyl magnesium bromide

Triphenylvinyl bromide

Downstream raw materials:

nitro-tris-(4-nitro-phenyl)-ethene

9-phenylphenanthrene

1,1,2-triphenylethane

2,2,3-triphenyloxirane

Refernces

Reactions of 1,1-Diphenylethylene and Its Derivatives with Tris(p-bromophenyl)aminium Hexachloroantimonate

10.1246/cl.1987.2251

The study investigates the dimerization of 1,1-diphenylethylene (1) and its derivatives using tris(p-bromophenyl)aminium hexachloroantimonate (3) as a new method to generate the cation radical. In dry solvents, 1 reacts with 3 to form indan dimer 2, while in wet solvents, butadiene derivative 7 and tetrahydrofuran derivative 8 are produced. The dimerization of derivatives like 1,1-diphenylpropene (4), 1,1-diphenyl-3-methyl-1-butene, 1,1,2-triphenylethylene (5), and 1,1-di-p-anisylethylene (6) yields different products, such as butadiene type dimer 9 from 4 in wet solvents, and cyclobutane type dimers 10, 11 from 5 and 12, 13 from 6. The study suggests that the substituents on 1,1-diphenylethylene and the methods for generating the cation radical are crucial for the types of dimers produced, though the exact reasons for the variant products remain unclear.