2-Cyclohexylnaphthalene

Base Information

• Chemical Name: 2-Cyclohexylnaphthalene
• CAS No.: 42044-07-5
• Molecular Formula: C16H18
• Molecular Weight: 210.319
• DSSTox Substance ID: DTXSID50472854
• Nikkaji Number: J89.435D
• Wikidata: Q82302037
• Mol file: 42044-07-5.mol

Synonyms:2-cyclohexylnaphthalene;2-cyclohexyl-naphthalene;42044-07-5;DTXSID50472854;LFOAKQQHKCCFNY-UHFFFAOYSA-N

Chemical Property of 2-Cyclohexylnaphthalene

Chemical Property:

• Melting Point: 31 °C
• Boiling Point: 150-152 °C(Press: 0.65 Torr)
• PSA: 0.00000
• Density: 1.0074 g/cm3(Temp: 40 °C)
• LogP: 4.88750
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 210.140850574
• Heavy Atom Count: 16
• Complexity: 214

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C2=CC3=CC=CC=C3C=C2

Technology Process of 2-Cyclohexylnaphthalene

There total 30 articles about 2-Cyclohexylnaphthalene 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%

2-Methoxynaphthalene (93-04-9) + cyclohexylmagnesium iodide (931-52-2) → 2-cyclohexylnaphthalene (42044-07-5)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; 1,2-bis-(dicyclohexylphosphino)ethane; In toluene; at 80 ℃; for 14h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/jacs.6b03253

Reference yield: 95.0%

1-bromocyclohexane (108-85-0) + 2-naphthalenylmagnesium bromide (21473-01-8) → 2-cyclohexylnaphthalene (42044-07-5)

Guidance literature:

With FeCl₂(N(C₂H₅)2CH₂CH₂NC(CH₃)CHC(CH₃)O); In diethyl ether; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1246/cl.2011.983

Reference yield: 85.0%

2-naphthyl pivalate (1503-86-2) + cyclohexylzinc(II) bromide (7565-57-3) → 2-cyclohexylnaphthalene (42044-07-5)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,2-bis-(dicyclohexylphosphino)ethane; In tetrahydrofuran; di-isopropyl ether; at 70 ℃; for 18h;

DOI:10.1021/acscatal.7b00941

upstream raw materials:

naphthalene

Cyclohexyl benzenesulphonate

2-(cyclohex-1-en-1-yl)naphthalene

cyclohexene

Downstream raw materials:

1-bromo-2-cyclohexylnaphthalene

2-phenylnaphthalene

Refernces

• 1、 Yue, Huifeng,Zhu, Chen,Shen, Li,Geng, Qiuyang,Hock, Katharina J.,Yuan, Tingting,Cavallo, Luigi,Rueping, Magnus. "Nickel-catalyzed C-N bond activation: Activated primary amines as alkylating reagents in reductive cross-coupling". . p. 4430 - 4435. Retrieved 2019/04/29.
• 2、 Sumida, Yuto,Sumida, Tomoe,Hosoya, Takamitsu. "Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides". . p. 3590 - 3601. Retrieved 2017/08/16.