2-Bromo-1,3,5-tricyclohexylbenzene

Base Information

• Chemical Name: 2-Bromo-1,3,5-tricyclohexylbenzene
• CAS No.: 97443-80-6
• Molecular Formula: C24H35Br
• Molecular Weight: 403.446
• Mol file: 97443-80-6.mol

Synonyms:Benzene,2-bromo-1,3,5-tricyclohexyl;2,4,6-tricyclohexylphenyl bromide;2,4,6-tricyclohexylbromobenzene;(2-bromobenzene-1,3,5-triyl)tricyclohexane;

Chemical Property of 2-Bromo-1,3,5-tricyclohexylbenzene

Chemical Property:

• Melting Point: 140-163°C
• Boiling Point: 454.9±44.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.155±0.06 g/cm3(Predicted)
• LogP: 8.59220
• Storage Temp.: 2-8°C

Purity/Quality:

98.0% ^*data from raw suppliers

1-Bromo-2,4,6-tricyclohexylbenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-Bromo-2,4,6-tricyclohexylbenzene is used for preparation of bulky biarylphosphine and uses as ligands in Pd-catalyzed C-O cross-coupling of aryl halides with phenols.

Technology Process of 2-Bromo-1,3,5-tricyclohexylbenzene

There total 4 articles about 2-Bromo-1,3,5-tricyclohexylbenzene 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: 82.0%

1,3,5-tricyclohexylbenzene (7325-14-6) → (2-bromobenzene-1,3,5-triyl)tricyclohexane (97443-80-6)

Guidance literature:

With bromine; In chloroform; at 0 - 40 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.202100980

Reference yield:

1-bromocyclohexane (108-85-0) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → (2-bromobenzene-1,3,5-triyl)tricyclohexane (97443-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum (III) chloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2: bromine / chloroform / 0 - 20 °C / Inert atmosphere

With aluminum (III) chloride; bromine; In dichloromethane; chloroform;

DOI:10.1021/ol202955h

Reference yield:

cyclohexylzinc chloride (256390-55-3) → (2-bromobenzene-1,3,5-triyl)tricyclohexane (97443-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tetrahydrofuran / 3.5 h / 18 °C / Schlenk technique; Inert atmosphere

2: bromine / chloroform / 3 h / 0 - 40 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bromine; palladium diacetate; In tetrahydrofuran; chloroform; 1: |Negishi Coupling;

DOI:10.1002/ejoc.202100980

upstream raw materials:

1,3,5-tricyclohexylbenzene

1-bromocyclohexane

benzene

1,3,5-trisbromobenzene

Downstream raw materials:

dichloro(2,4,6-tris[bis(trimethylsilyl)methyl]phenyl)(2,4,6-tricyclohexylphenyl)stannane

2,4,6-tris[bis(trimethylsilyl)methyl]phenyl(2,4,6-tricyclohexylphenyl)Sn=Se

5-(2,4,6-tricyclohexylphenyl)-5-[2,4,6-tris[bis(trimethylsilyl)methyl]phenyl]-1,2,3,4,5-tetraselenastannolane

(2,4,6-tris[bis(trimethylsilyl)methyl]phenyl)(2,4,6-tricyclohexylphenyl)stannane