2-(2-Dicyclohexylphosphanyl-phenyl)-1-Methyl-1H-indole

Base Information

• Chemical Name: 2-(2-Dicyclohexylphosphanyl-phenyl)-1-Methyl-1H-indole
• CAS No.: 1067883-58-2
• Molecular Formula: C27H34NP
• Molecular Weight: 403.547
• Hs Code.: 2933990090
• Mol file: 1067883-58-2.mol

Synonyms:2-(2-Dicyclohexylphosphanyl-phenyl)-1-Methyl-1H-indole;2-[2-(Dicyclohexylphosphino)phenyl]-1-methyl-1H-indole;2-[2-(Dicyclohexylphosphino)phenyl]-N-methylindole;2-[2-(Dicyclohexylphosphino)phenyl]-1-Methyl-1H-indole, Min. 98% CM-Phos;2-(2-(dicyclohexylphosphino)phenyl)-1-Methyl-indole;CM-Phos

Chemical Property of 2-(2-Dicyclohexylphosphanyl-phenyl)-1-Methyl-1H-indole

Chemical Property:

• Melting Point: 180-185℃
• Boiling Point: 582.4±33.0 °C(Predicted)
• PSA: 18.52000
• LogP: 7.61790

Purity/Quality:

99% ^*data from raw suppliers

2-[2-(Dicyclohexylphosphino)phenyl]-1-methyl-1H-indole, min. 98% CM-Phos ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(2-Dicyclohexylphosphanyl-phenyl)-1-Methyl-1H-indole

There total 2 articles about 2-(2-Dicyclohexylphosphanyl-phenyl)-1-Methyl-1H-indole 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: 88.0%

N-methyl-2-(2'-bromophenyl)-1H-indole (1067883-80-0) + chlorodicyclohexylphosphane (16523-54-9) → 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole (1067883-58-2)

Guidance literature:

N-methyl-2-(2'-bromophenyl)-1H-indole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

chlorodicyclohexylphosphane; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1021/jo8014819

Reference yield:

2-bromophenyl methyl ketone (2142-69-0) + 1-Methyl-1-phenylhydrazine (618-40-6) → 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole (1067883-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Inert atmosphere

2: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; 1: |Fischer Indole Synthesis;

DOI:10.1002/anie.201208025

Reference yield: 99.0%

2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole (1067883-58-2) + palladium diacetate (3375-31-3) → [palladium(II)(C8H4N(Me)C6H4(PCy2)OOC(CH3))]2 (1070731-49-5)

Guidance literature:

With sodium hydroxide; In dichloromethane; react. of Pd(OAc)2 and C8H5N(CH3)C6H4(P(C6H11)2) under basic conditions (NaOH) at room temp. for 1 h; crystd. from CH2Cl2 soln. layered with hexane at room temp., detd. by XRD;

DOI:10.1002/anie.200802157

upstream raw materials:

N-methyl-2-(2'-bromophenyl)-1H-indole

chlorodicyclohexylphosphane

2-bromophenyl methyl ketone

1-Methyl-1-phenylhydrazine

Downstream raw materials:

[palladium(II)(C₈H₄N(Me)C₆H₄(PCy₂)OOC(CH₃))]2

Refernces

• 1、 So, Chau Ming,Lau, Chak Po,Chan, Albert S. C.,Kwong, Fuk Yee. "Suzuki-Miyaura coupling of aryl tosylates catalyzed by an array of indolyl phosphine-palladium catalysts". . p. 7731 - 7734. Retrieved 2008/12/22.
• 2、 So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee. "A general palladium-catalyzed Suzuki-Miyaura coupling of aryl mesylates". supporting information; experimental part. p. 8059 - 8063. Retrieved 2009/04/13.