1,1'-Binaphthalene

Base Information

• Chemical Name: 1,1'-Binaphthalene
• CAS No.: 604-53-5
• Deprecated CAS: 32507-32-7
• Molecular Formula: C20H14
• Molecular Weight: 254.331
• Hs Code.: 29029090
• European Community (EC) Number: 210-070-6
• NSC Number: 662279,15230
• UNII: T87T28S609
• DSSTox Substance ID: DTXSID70870671
• Nikkaji Number: J38.978A,J38.979J,J6.813F
• Wikipedia: 1,1'-Binaphthyl
• Wikidata: Q27289804
• Mol file: 604-53-5.mol

Synonyms:1,1'-binaphthyl

Chemical Property of 1,1'-Binaphthalene

Chemical Property:

• Appearance/Colour: Brown powder
• Melting Point: 143-146 °C
• Refractive Index: 1.6292 (estimate)
• Boiling Point: 405 °C at 760 mmHg
• Flash Point: 192.1 °C
• PSA: 0.00000
• Density: 1.14 g/cm³
• LogP: 5.66000
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: very faint turbidity in Toluene
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 254.109550447
• Heavy Atom Count: 20
• Complexity: 288

Purity/Quality:

98% ^*data from raw suppliers

1,1'-Binaphthyl >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2C3=CC=CC4=CC=CC=C43

Technology Process of 1,1'-Binaphthalene

There total 249 articles about 1,1'-Binaphthalene 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: 55.0%

1,4-bromoiodobenzene (589-87-7) + 1-Iodonaphthalene (90-14-2) → 1,1'-bisnaphthalene (604-53-5) + 4-(4-bromophenyl)bromobenzene (92-86-4) + 1-(4-bromo-phenyl)-naphthalene (204530-94-9)

Guidance literature:

With palladium diacetate; potassium carbonate; In butanone; at 120 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol802865c

Reference yield: 29.0%

naphthalene (91-20-3,71998-51-1,72931-45-4) → 1,1'-bisnaphthalene (604-53-5) + 1-(naphthalen-2-yl)naphthalene (4325-74-0) + 2,2'-binaphthalene (612-78-2) + PERYLENE (198-55-0)

Guidance literature:

With iron(III) perchlorate; In acetonitrile; at 28 ℃; for 2h;

Reference yield: 21.0%

naphthalene radical cation hexafluorophosphate + tetrabutylammonium thiocyanate (3674-54-2) → 2-naphthyl isothiocyanate (1636-33-5) + 1,1'-bisnaphthalene (604-53-5) + α-naphthyl thiocyanate (16671-89-9) + 1-isothiocyanatonaphthalene (551-06-4)

Guidance literature:

In dichloromethane; at -78 ℃;

upstream raw materials:

naphthalene

[1,1'-binaphthalene]-3,3',4,4'-tetraone

1-Bromonaphthalene

1-Iodonaphthalene

Downstream raw materials:

PERYLENE

2,2'-binaphthalene

naphthalene

Benzo[j]fluoranthene

Refernces

• 1、 Brath, Henrich,Dubovska, Margareta,Juricek, Michal,Kasak, Peter,Putala, Martin. "Novel route to enantiopure 2,2′-diaryl-1,1′-binaphthalenes by stereoconservative Suzuki arylation at positions 2 and 2′". . p. 1517 - 1536. Retrieved 2004.
• 2、 Jouikov, Viatcheslav,Simonet, Jacques. "Cleavage of aryl iodides at carbon cathodes in organic carbonates. Surfaces doped by transition metals at the nanometric scale: Electro or redox catalysis?". . p. 1262 - 1265. Retrieved 2010.
• 3、 Yoshimoto,Itatani. "". . p. 2490. Retrieved 1973.
• 4、 Pincock,Wilson. "". . p. 1291. Retrieved 1971.
• 5、 Pelletier,Locke. "-". . p. 131. Retrieved 1958.
• 6、 Hutchins, Larry G.,Pincock, Richard E.. "Platinum-Catalyzed Racemization of 1,1'-Binaphthyl". . p. 607 - 610. Retrieved 1982.
• 7、 Liang, Tongling,Lin, Wenhua,Ma, Yanping,Sun, Wen-Hua,Zhang, Liping. "Sterically enhanced 2-iminopyridylpalladium chlorides as recyclable ppm-palladium catalyst for Suzuki–Miyaura coupling in aqueous solution". . . Retrieved 2021/10/20.
• 8、 Minus, Matthew B.,Moor, Sarah R.,Pary, Fathima F.,Nirmani,Chwatko, Malgorzata,Okeke, Brandon,Singleton, Josh E.,Nelson, Toby L.,Lynd, Nathaniel A.,Anslyn, Eric V.. ""benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers". supporting information. p. 2873 - 2877. Retrieved 2021/05/05.