9-[4-(Trifluoromethyl)phenyl]anthracene

Base Information

• Chemical Name: 9-[4-(Trifluoromethyl)phenyl]anthracene
• CAS No.: 386-23-2
• Molecular Formula: C21H13F3
• Molecular Weight: 322.329
• NSC Number: 99567
• DSSTox Substance ID: DTXSID50295085
• Nikkaji Number: J1.000.751H
• Wikidata: Q82034783
• Mol file: 386-23-2.mol

Synonyms:9-[4-(trifluoromethyl)phenyl]anthracene;386-23-2;NSC99567;SCHEMBL4728663;DTXSID50295085;NSC-99567;9-(4-trifluoromethylphenyl)anthracene

Chemical Property of 9-[4-(Trifluoromethyl)phenyl]anthracene

Chemical Property:

• Vapor Pressure: 2.82E-06mmHg at 25°C
• Boiling Point: 401°C at 760 mmHg
• Flash Point: 164.7°C
• Density: 1.256g/cm³
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 322.09693490
• Heavy Atom Count: 24
• Complexity: 399

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C3C=CC=CC3=C2C4=CC=C(C=C4)C(F)(F)F

Technology Process of 9-[4-(Trifluoromethyl)phenyl]anthracene

There total 7 articles about 9-[4-(Trifluoromethyl)phenyl]anthracene 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: 97.0%

anthracen-9-yl pivalate + 4-trifluoromethylphenylboronic acid (128796-39-4) → 9-(4-(trifluoromethyl)phenyl)anthracene (386-23-2)

Guidance literature:

With potassium phosphate monohydrate; (NC₅H₃(N₂C₇H₄(CH₂)3CH₃)2)NiBr⁽¹⁺⁾*Br^(1-)=Ni(NC₅H₃(N₂C₇H₄(CH₂)3CH₃)2)Br₂; tricyclohexylphosphine; In toluene; at 120 ℃; for 12h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c3cc46663a

Reference yield: 89.0%

9-Bromoanthracene (1564-64-3) + 4-trifluoromethylphenylboronic acid (128796-39-4) → 9-(4-(trifluoromethyl)phenyl)anthracene (386-23-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; toluene; for 24h; Inert atmosphere; Reflux; Sealed tube;

DOI:10.1021/jacs.9b03328

Reference yield: 81.0%

p-trifluoromethylphenyl bromide (402-43-7) + anthracene-9-boronic acid (100622-34-2) → 9-(4-(trifluoromethyl)phenyl)anthracene (386-23-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; Reflux; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01315

upstream raw materials:

2-benzyl-4'-trifluoromethyl-benzophenone

1,4-diaza-bicyclo[2.2.2]octane

hydrogen bromide

acetic acid

Refernces

• 1、 Han, Bo,Ma, Pengchen,Cong, Xuefeng,Chen, Hui,Zeng, Xiaoming. "Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study". supporting information. p. 9018 - 9026. Retrieved 2019/06/13.
• 2、 Shih, Wei-Chih,Chiang, Yun-Ting,Wang, Qing,Wu, Ming-Chun,Yap, Glenn P. A.,Zhao, Lili,Ong, Tiow-Gan. "Invisible Chelating Effect Exhibited between Carbodicarbene and Phosphine through π-π Interaction and Implication in the Cross-Coupling Reaction". supporting information. p. 4287 - 4297. Retrieved 2017/11/20.