2-Phenylnaphthalene

Base Information

• Chemical Name: 2-Phenylnaphthalene
• CAS No.: 612-94-2
• Molecular Formula: C16H12
• Molecular Weight: 204.271
• Hs Code.: 29334990
• European Community (EC) Number: 210-324-6
• NSC Number: 407592
• UNII: 949VN5DH7A
• DSSTox Substance ID: DTXSID8060614
• Nikkaji Number: J117.144E
• Wikidata: Q27271663
• Mol file: 612-94-2.mol

Synonyms:2-PHENYLNAPHTHALENE;612-94-2;Naphthalene, 2-phenyl-;.beta.-Phenylnaphthalene;Naphthalene, phenyl-;beta-Phenylnaphthalene;NSC 407592;UNII-949VN5DH7A;949VN5DH7A;EINECS 210-324-6;NSC-407592;35465-71-5;2-Phenylnaphthalene 10 microg/mL in Cyclohexane;2-Phenylnaphthalin;6-phenylnaphthalene;2-phenyl-naphthalene;c1(ccc2ccccc2c1)c3ccccc3;DTXSID8060614;MFCD00039601;NSC407592;AKOS016015924;SS-4770;CS-0269833;FT-0632555;P0679;T72706;A868752;Q27271663;Z1723549920

Chemical Property of 2-Phenylnaphthalene

Chemical Property:

• Vapor Pressure: 0.000122mmHg at 25°C
• Melting Point: 105 °C
• Refractive Index: 1.6664 (estimate)
• Boiling Point: 358 °C
• Flash Point: 155.9°C
• PSA: 0.00000
• Density: 1.081g/cm³
• LogP: 4.50680
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 204.093900383
• Heavy Atom Count: 16
• Complexity: 214

Purity/Quality:

99% ^*data from raw suppliers

2-Phenylnaphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC3=CC=CC=C3C=C2

Technology Process of 2-Phenylnaphthalene

There total 582 articles about 2-Phenylnaphthalene 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: 80.0%

iodobenzene (591-50-4) + naphthalene-2-boronic acid (32316-92-0) → 2-phenylnaphthalene (612-94-2) + 2,2'-binaphthalene (612-78-2)

Guidance literature:

With trans-1,2-Diaminocyclohexane; potassium tert-butylate; silver(I) acetate; In dimethyl sulfoxide; at 150 ℃; for 10h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.09.127

Reference yield: 80.0%

naphthalene-2-boronic acid (32316-92-0) + phenylboronic acid (98-80-6) → 2-phenylnaphthalene (612-94-2) + 2,2'-binaphthalene (612-78-2)

Guidance literature:

With potassium carbonate; In water; acetonitrile; at 70 ℃; chemoselective reaction; Schlenk technique;

DOI:10.1002/asia.201800358

Reference yield: 73.0%

1-(2-((4-methoxyphenyl)ethynyl)phenyl)-3-phenylprop-2-yn-1-ol → (4-methoxyphenyl)(2-phenylnaphthalen-1-yl)methanone + 2-phenylnaphthalene (612-94-2) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

(triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate; In dichloromethane; at 23 ℃; for 3h;

DOI:10.1039/b618291g

upstream raw materials:

pyrrolidine

diethyl ether

phenyllithium

1-Chloronaphthalene

Downstream raw materials:

3-cyclohexylbicyclo<4.4.0>decane

1-bromo-2-phenylnaphthalene

1-nitro-2-phenylnaphthalene

1,5-dinitro-2-phenyl-naphthalene

Refernces

Synthesis of 2-phenylnaphthalenes through gold-catalyzed dimerization via a highly selective carbon nucleophile pathway

10.1021/jo200352j

The study presents a novel method for the synthesis of 2-phenylnaphthalenes, which are important structural motifs found in pharmaceuticals, natural products, and agrochemicals, through gold-catalyzed dimerization. The researchers utilized various gold catalysts, such as AuCl3/AgSbF6, AgOTf/Au(PPh3)Cl, and AgSbF6/Au(PPh3)Cl, along with substrates like N-butyl-2-(2-ethynylphenyl)acetamide (1a) and its derivatives, to optimize the reaction conditions for high selectivity and yield. The purpose of these chemicals was to explore the nucleophilic addition reactions, particularly focusing on the carbon nucleophiles, which are less common in gold-catalyzed reactions. The study successfully demonstrated that the benzyl carbon could act as a nucleophilic center in the presence of amide nitrogen and acetate oxygen, leading to the formation of naphthalene scaffolds through the dimerization of reactants. This discovery expands the scope of gold-catalyzed reactions and offers a new approach to synthesize potentially useful heterocycles.