9,9'-Biphenanthrene

Base Information

• Chemical Name: 9,9'-Biphenanthrene
• CAS No.: 20532-03-0
• Molecular Formula: C28H18
• Molecular Weight: 354.451
• Hs Code.: 2902909090
• European Community (EC) Number: 660-916-7
• DSSTox Substance ID: DTXSID30174526
• Nikkaji Number: J633.373G
• Wikidata: Q83044604
• Mol file: 20532-03-0.mol

Synonyms:9,9'-Biphenanthrene;9,9'-Biphenanthryl;20532-03-0;DTXSID30174526;UPAPZXUZBAAZCB-UHFFFAOYSA-N;AKOS024433705

Chemical Property of 9,9'-Biphenanthrene

Chemical Property:

• Melting Point: 188-189 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 544.4°Cat760mmHg
• Flash Point: 280.6°C
• PSA: 0.00000
• Density: 1.217g/cm³
• LogP: 7.96640
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 354.140850574
• Heavy Atom Count: 28
• Complexity: 488

Purity/Quality:

9,9'-BIPHENANTHRENE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C3=CC=CC=C23)C4=CC5=CC=CC=C5C6=CC=CC=C64

Technology Process of 9,9'-Biphenanthrene

There total 5 articles about 9,9'-Biphenanthrene 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: 90.0%

9-phenanthrenylboronic acid (68572-87-2) → 9,9'-biphenanthrene (20532-03-0)

Guidance literature:

With C₃₄H₅₄N₂O₂; palladium diacetate; potassium carbonate; p-toluenesulfonyl chloride; In water; at 0 - 25 ℃; for 0.25h; Reagent/catalyst; Green chemistry;

DOI:10.1002/aoc.3033

Reference yield: 55.7%

phenanthrene (85-01-8) → 9,9'-biphenanthrene (20532-03-0) + 9-chlorophenanthrene (947-72-8)

Guidance literature:

With Iodine monochloride; In acetonitrile; for 24h;

DOI:10.1021/jo00103a026

Reference yield:

potassiumhexacyanoferrate(II) trihydrate + 9-bromophenanthrene (573-17-1) → 9-cyanophenanthrene (2510-55-6) + 9,9'-biphenanthrene (20532-03-0)

Guidance literature:

With [Pd{C₆H₄(CH₂N(CH₂Ph)₂)}(μ-Br)]₂; tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1016/j.tetlet.2011.11.087

upstream raw materials:

phenanthrene

9-phenanthrenylboronic acid

9-bromophenanthrene

1-bromo-2-methoxynaphthalene

Downstream raw materials:

2'-Methyl-2,9-phenanthrylmethyl-biphenyl

Refernces

• 1、 Zhang, Dao,Yu, Jueqin. "Fine Tuning of Chiral Bis(N-heterocyclic carbene) Palladium Catalysts for Asymmetric Suzuki-Miyaura Cross-Coupling Reactions: Exploring the Ligand Modification". . p. 1269 - 1280. Retrieved 2020/05/05.
• 2、 Kapdi, Anant R.,Dhangar, Gopal,Serrano, Jose Luis,De Haro, Jose A.,Lozano, Pedro,Fairlamb, Ian J. S.. "Palladacycles promote the base-free homocoupling of arylboronic acids in air at room temperature". . p. 55305 - 55312. Retrieved 2015/02/18.