Rockphos

Base Information

• Chemical Name: Rockphos
• CAS No.: 1262046-34-3
• Molecular Formula: C₃₁H₄₉OP
• Molecular Weight: 468.703
• Mol file: 1262046-34-3.mol

Synonyms:2-(Di-t-butylphosphino)-3-methoxy-6-methyl-2',4',6'-tri-i-propyl-1,1'-biphenyl;di-tert-butyl(2',4′,6′-triisopropyl-3-methoxy-6-methyl-[1,1′-biphenyl]-2-yl)phosphine;Di-tert-butyl(2',4',6'-triisopropyl-3-methoxy-6-methyl-[1,1'-biphenyl]-2-yl)phosphine;2-Di(tert-butyl)phosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl;2-(DI-T-BUTYLPHOSPHINO)-3-METHOXY-6-METHYL-2'-4'-6'-TRI-I-PROPYL-1,1'-BIPHENYL;2-(3-METHOXYPHENYL)PROPAN-2-AMINE;

Chemical Property of Rockphos

Chemical Property:

• Melting Point: 129-130°C
• Boiling Point: 526.6±50.0 °C(Predicted)
• PSA: 22.82000
• LogP: 9.74500
• Storage Temp.: 15-25°C

Purity/Quality:

98% ^*data from raw suppliers

Rockpahos ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Rockpahos is commonly used as a catalyst in organic reactions along with a palladium compound catalyst. RockPhos is a biphenyl-based phosphine ligand used with Pd(0) catalyst for carbon-carbon and carbon-heteroatom bond formation reactions.It can also be employed in the: 2-fluroethoxylation of bromo-chalcones in the presence of palladium catalyst.Conversion of aryl chlorides into aryl methoxides using RockPhos Pd G3 as a catalyst.

Technology Process of Rockphos

There total 8 articles about Rockphos 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: 87.0%

di(tert-butyl)chlorophosphine (13716-10-4) + 2-bromo-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (1402393-57-0) → di-tert-butyl (2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1‘-biphenyl]-2-yl)phosphine (1262046-34-3)

Guidance literature:

2-bromo-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl; With magnesium; ethylene dibromide; In tetrahydrofuran; toluene; at 80 ℃; for 3h; Inert atmosphere;

di(tert-butyl)chlorophosphine; With copper(l) chloride; lithium bromide; In tetrahydrofuran; toluene; at 120 ℃; for 18h; Inert atmosphere;

DOI:10.1002/adsc.201200398

Reference yield: 72.0%

di(tert-butyl)chlorophosphine (13716-10-4) + 2-iodo-2',4',6'-triisopropyl-3-methoxy-6-methyl-1,1'-biphenyl (1351403-03-6) → di-tert-butyl (2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1‘-biphenyl]-2-yl)phosphine (1262046-34-3)

Guidance literature:

2-iodo-2',4',6'-triisopropyl-3-methoxy-6-methyl-1,1'-biphenyl; With tert.-butyl lithium; In toluene; pentane; at -78 ℃; for 0.666667h; Inert atmosphere;

di(tert-butyl)chlorophosphine; With copper(l) chloride; In tetrahydrofuran; pentane; at -78 - 140 ℃; for 20h; Inert atmosphere;

DOI:10.1002/anie.201104361

Reference yield:

3-fluoro-4-methyl phenol (452-78-8) → di-tert-butyl (2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1‘-biphenyl]-2-yl)phosphine (1262046-34-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / acetone / 3 h / Reflux; Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

2.3: 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: tert.-butyl lithium / toluene; pentane / 0.67 h / -78 °C / Inert atmosphere

3.2: 20 h / -78 - 140 °C / Inert atmosphere

With n-butyllithium; tert.-butyl lithium; potassium carbonate; In tetrahydrofuran; hexane; acetone; toluene; pentane;

DOI:10.1002/anie.201104361

upstream raw materials:

di(tert-butyl)chlorophosphine

2-iodo-2',4',6'-triisopropyl-3-methoxy-6-methyl-1,1'-biphenyl

3-fluoro-4-methyl phenol

2,4,6-triisopropyl-1-bromobenzene

Downstream raw materials:

PdBrC₆H₄(CH₂)3CH₃C₆H₂(CH(CH₃)2)3C₆H₂OCH₃CH₃P(C(CH₃)3)2

PdFC₆H₄(CH₂)3CH₃C₆H₂(CH(CH₃)2)3C₆H₂OCH₃CH₃P(C(CH₃)3)2

Refernces

• 1、 Hoshiya, Naoyuki,Buchwald, Stephen L.. "An improved synthesis of brettphos- and rockphos-type biarylphosphine ligands". experimental part. p. 2031 - 2037. Retrieved 2012/10/08.
• 2、 Maimone, Thomas J.,Milner, Phillip J.,Kinzel, Tom,Zhang, Yong,Takase, Michael K.,Buchwald, Stephen L.. "Evidence for in situ catalyst modification during the Pd-catalyzed conversion of aryl triflates to aryl fluorides". scheme or table. p. 18106 - 18109. Retrieved 2012/01/02.