6-Chloro-1-phenylnaphthalene

Base Information

• Chemical Name: 6-Chloro-1-phenylnaphthalene
• CAS No.: 1071042-32-4
• Molecular Formula: C₁₆H₁₁Cl
• Molecular Weight: 238.716
• DSSTox Substance ID: DTXSID00704798
• Wikidata: Q82637354
• Mol file: 1071042-32-4.mol

Synonyms:6-Chloro-1-phenylnaphthalene;1071042-32-4;DTXSID00704798;FT-0728827

Chemical Property of 6-Chloro-1-phenylnaphthalene

Chemical Property:

• PSA: 0.00000
• LogP: 5.16020
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 238.0549280
• Heavy Atom Count: 17
• Complexity: 244

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=CC3=C2C=CC(=C3)Cl

Technology Process of 6-Chloro-1-phenylnaphthalene

There total 6 articles about 6-Chloro-1-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: 90.0%

2-chloro-7,12-epoxy-5,6,6a,7,12,12a-hexahydro-5-phenylbenz[a]anthracen-5-ol → 6-chloro-1-phenylnaphthalene (1071042-32-4)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; for 30h; Reflux; Inert atmosphere;

DOI:10.1039/c1cc15095b

Reference yield:

2-(3-chlorophenyl)acetaldehyde (41904-40-9) + phenylacetylene (536-74-3) → 1-chloro-8-phenylnaphthalene (940006-25-7) + 6-chloro-1-phenylnaphthalene (1071042-32-4)

Guidance literature:

With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 80 ℃; for 15h; Overall yield = 30 %; Overall yield = 21.4 mg; Schlenk technique;

DOI:10.1007/s11426-013-4843-7

Reference yield:

4-chlorobenzoylmethyl bromide (536-38-9) → 6-chloro-1-phenylnaphthalene (1071042-32-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetone / 0 °C / Inert atmosphere

2.1: ethyl acetate / 0.25 h / Reflux; Inert atmosphere

2.2: Reflux; Inert atmosphere

3.1: n-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / ethanol / 30 h / Reflux; Inert atmosphere

With n-butyllithium; toluene-4-sulfonic acid; In diethyl ether; ethanol; ethyl acetate; acetone; 4.1: retro Diels-Alder reaction;

DOI:10.1039/c1cc15095b

upstream raw materials:

iodobenzene

O-ethyl S-2-(4-chlorophenyl)-2-oxoethyl carbonodithioate

4-chlorobenzoylmethyl bromide

2-(3-chlorophenyl)acetaldehyde

Refernces

• 1、 Guignard, Raphael F.,Zard, Samir Z.. "A convergent approach to polycyclic aromatic hydrocarbons". . p. 12185 - 12187. Retrieved 2011/12/15.