2-(Di-tert-butylphosphino)biphenyl

Base Information

• Chemical Name: 2-(Di-tert-butylphosphino)biphenyl
• CAS No.: 224311-51-7
• Molecular Formula: C20H27P
• Molecular Weight: 298.408
• Hs Code.: HOSPHINO)BIPHENYL PRODUCT IDENTIFICATION
• UNII: 5Y743P380H
• DSSTox Substance ID: DTXSID50370169
• Nikkaji Number: J1.124.970A,J3.246.742C,J3.255.696E
• Wikidata: Q27263038
• Mol file: 224311-51-7.mol

Synonyms:(Biphenyl-2-yl)bis(tert-butyl)phosphine;2-(Di-tert-butylphosphino)-1,1'-biphenyl;2-Biphenylyl-di-tert-butylphosphine;Di(tert-butyl)(1,1'-biphenyl-2-yl)phosphine;Di(tert-butyl)(2-phenylphenyl)phosphine;Di-tert-butyl-o-biphenylphosphine;JohnPhos;[1,1'-biphenyl]-2-ylbis(1,1-dimethylethyl)phosphine;

Chemical Property of 2-(Di-tert-butylphosphino)biphenyl

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.05E-06mmHg at 25°C
• Melting Point: 86-88 °C(lit.)
• Boiling Point: 405.5 °C at 760 mmHg
• Flash Point: 210.1 °C
• PSA: 13.59000
• Density: 1 g/cm³
• LogP: 6.05780
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly, Heated, Sonic
• Water Solubility.: Insoluble
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 298.185037859
• Heavy Atom Count: 21
• Complexity: 300

Purity/Quality:

99% ^*data from raw suppliers

2-(Di-tert-butylphosphino)biphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C
• Uses: suzuki reaction 2-(Di-tert-butylphosphino)biphenyl (also known as JohnPhos) is a Buchwald ligand that is highly efficient in palladium-catalyzed reactions.

Technology Process of 2-(Di-tert-butylphosphino)biphenyl

There total 9 articles about 2-(Di-tert-butylphosphino)biphenyl 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: 95.7%

di(tert-butyl)chlorophosphine (13716-10-4) + 2-Bromobiphenyl (2052-07-5) → johnphos (224311-51-7)

Guidance literature:

2-Bromobiphenyl; With magnesium; In tetrahydrofuran; for 2h; Inert atmosphere; Reflux;

di(tert-butyl)chlorophosphine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 2h; Reagent/catalyst; Reflux; Inert atmosphere;

Reference yield: 88.0%

di-tert-butylphosphine (819-19-2) + 2,3-dibromobenzene (583-53-9) + phenylboronic acid (98-80-6) → johnphos (224311-51-7)

Guidance literature:

di-tert-butylphosphine; 2,3-dibromobenzene; With bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium⁽⁰⁾; sodium carbonate; In toluene; at 100 ℃; for 6h; Inert atmosphere;

phenylboronic acid; In toluene; at 80 ℃; for 10h; Inert atmosphere;

Reference yield: 87.5%

di(tert-butyl)chlorophosphine (13716-10-4) + 2-biphenylmagnesium bromide (82214-69-5) → johnphos (224311-51-7)

Guidance literature:

copper(I) bromide; In tetrahydrofuran; at 30 - 35 ℃; for 4h; Heating / reflux;

upstream raw materials:

di(tert-butyl)chlorophosphine

2-Bromobiphenyl

2-biphenylmagnesium bromide

ammonium hydroxide

Downstream raw materials:

4-(5-bromo-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester

[3-(4-Methyl-piperazin-1-yl)-5,6,7,8-tetrahydro-naphthalen-1-yl]-acetic Acid Ethyl Ester

1-(2,6-dihydroxy-4-morpholin-4-yl-phenyl)-ethanone

biphenyl-4-acetaldehyde

Refernces

• 1、 -. "Synthesis of di-tert-butylphenol [...] biphenyl compounds (by machine translation)". Paragraph 0012. . Retrieved 2019/03/06.
• 2、 Hu, Rong-Bin,Zhang, Heng,Zhang, Xiao-Yu,Yang, Shang-Dong. "Palladium-catalyzed P(O)R2 directed C-H arylation to synthesize electron-rich polyaromatic monophosphorus ligands". . p. 2193 - 2195. Retrieved 2014/02/14.