Di-tert-butyl(2'-methyl-[1,1'-biphenyl]-2-yl)phosphine

Base Information

• Chemical Name: Di-tert-butyl(2'-methyl-[1,1'-biphenyl]-2-yl)phosphine
• CAS No.: 255837-19-5
• Molecular Formula: C21H29P
• Molecular Weight: 312.435
• Hs Code.: 29319090
• European Community (EC) Number: 607-748-2
• DSSTox Substance ID: DTXSID30370586
• Nikkaji Number: J1.270.935H
• Wikidata: Q72470098
• Mol file: 255837-19-5.mol

Synonyms:255837-19-5;Di-tert-butyl(2'-methyl-[1,1'-biphenyl]-2-yl)phosphine;2-(Di-tert-butylphosphino)-2'-methylbiphenyl;tBuMePhos;2-(DI-T-BUTYLPHOSPHINO)-2'-METHYLBIPHENYL;2-DI-TERT-BUTYLPHOSPHINO-2'-METHYLBIPHENYL;ditert-butyl-[2-(2-methylphenyl)phenyl]phosphane;MFCD03453047;2-di-t-butylphosphino-2'-methylbiphenyl;PHOSPHINE, BIS(1,1-DIMETHYLETHYL)(2'-METHYL[1,1'-BIPHENYL]-2-YL)-;t-Butyl MePhos;di-tert-butyl(2'-methylbiphenyl-2-yl)phosphane;di-tert-butyl(2'-methylbiphenyl-2-yl)phosphine;DI-TERT-BUTYL({2'-METHYL-[1,1'-BIPHENYL]-2-YL})PHOSPHANE;C21H29P;tBuMePhos, 97%;SCHEMBL196673;DTXSID30370586;UJONYAVMBYXBJQ-UHFFFAOYSA-N;AMY11680;BCP05524;BBL102970;STL556779;AKOS015999751;CS-W008225;GC10153;2-Di-t-butylphosphino-2'-methyl-biphenyl;AS-64898;SY009814;2-(Di-t-butylphosphino)-2'-methybiphenyl;Ditert-butyl-[2-(o-tolyl)phenyl]phosphane;2-(di-tert-butylphospino)-2'-methylbiphenyl;2-(Ditert-butylphosphino)-2'-methylbiphenyl;BB 0322701;di-t-butyl(2'-methylbiphenyl-2-yl)phosphine;FT-0688118;di-tert-butyl(2'-methyl-2-biphenylyl)phosphine;EN300-7399678;A857887;J-509284;Y-200023;bis(1,1-dimethylethyl)(2'-methyl-2-biphenylyl)phosphane;Di-tert-butyl(2'-methyl[1,1'-biphenyl]-2-yl)phosphane;Not available;2-Di-tert-butylphosphino-2'-methylbiphenyl;bis(1,1-dimethylethyl) (2'-methyl-2-biphenylyl)phosphane;2-Di-tert-butylphosphino-2 inverted exclamation mark -methylbiphenyl

Chemical Property of Di-tert-butyl(2'-methyl-[1,1'-biphenyl]-2-yl)phosphine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 91-93 °C
• Boiling Point: 408 °C at 760 mmHg
• Flash Point: 211.7 °C
• PSA: 13.59000
• LogP: 6.36620
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Air Sensitive
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 312.200687923
• Heavy Atom Count: 22
• Complexity: 332

Purity/Quality:

98% ^*data from raw suppliers

2-(Di-Tert-Butylphosphino)-2''-Methylbiphenyl ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C
• Uses: suzuki reaction A ligand for the palladium-catalyzed monoarylation of malonate esters, 1,3-diketones and isolated nitroalkanes.

Technology Process of Di-tert-butyl(2'-methyl-[1,1'-biphenyl]-2-yl)phosphine

There total 5 articles about Di-tert-butyl(2'-methyl-[1,1'-biphenyl]-2-yl)phosphine 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%

di-tert-butylphosphine (819-19-2) + 2-Methylphenylboronic acid (16419-60-6) + 2,3-dibromobenzene (583-53-9) → di-tert-butyl (2'-methyl-[1,1'-biphenyl]-2-yl)phosphine (255837-19-5)

Guidance literature:

di-tert-butylphosphine; 2,3-dibromobenzene; With bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium⁽⁰⁾; sodium carbonate; In toluene; at 80 ℃; for 6h; Inert atmosphere;

2-Methylphenylboronic acid; In toluene; at 100 ℃; for 10h; Inert atmosphere;

Reference yield: 50.0%

di(tert-butyl)chlorophosphine (13716-10-4) + 2-bromo-1-chlorobenzene (694-80-4) + 2-methylphenyl bromide (95-46-5) → di-tert-butyl (2'-methyl-[1,1'-biphenyl]-2-yl)phosphine (255837-19-5)

Guidance literature:

2-methylphenyl bromide; With magnesium; In tetrahydrofuran; at 60 ℃; for 2h;

2-bromo-1-chlorobenzene; In tetrahydrofuran; at 60 ℃; for 2h;

di(tert-butyl)chlorophosphine; With copper(l) chloride; In tetrahydrofuran; at 60 ℃; for 12h; Further stages.;

DOI:10.1021/jo000691h

Reference yield: 33.0%

di(tert-butyl)chlorophosphine (13716-10-4) + 2-bromo-2'-methylbiphenyl (251320-87-3) → di-tert-butyl (2'-methyl-[1,1'-biphenyl]-2-yl)phosphine (255837-19-5)

Guidance literature:

2-bromo-2'-methylbiphenyl; With magnesium; In tetrahydrofuran; at 65 ℃; for 4.5h;

di(tert-butyl)chlorophosphine; With copper(l) chloride; In tetrahydrofuran; at 65 ℃; for 16h; Further stages.;

DOI:10.1021/ja993912d

upstream raw materials:

di(tert-butyl)chlorophosphine

2-bromo-2'-methylbiphenyl

2-bromo-1-chlorobenzene

2-methylphenyl bromide

Downstream raw materials:

(2-di-t-butylphosphino-2'-methylbiphenyl-3-yl)(η4-1,5-cyclooctadiene)iridium(I)

di-μ-chlorido-[(η4-1,5-cyclooctadiene)iridium(I)][(2-di-t-butylphosphino-2'-methylbiphenyl)silver(I)]

Refernces

• 1、 Zhang, Heng,Hu, Rong-Bin,Zhang, Xiao-Yu,Li, Shi-Xia,Yang, Shang-Dong. "Palladium-catalyzed R2(O)P directed C(sp2)-H acetoxylation". supporting information. p. 4686 - 4689. Retrieved 2014/05/06.
• 2、 Tomori, Hiroshi,Fox, Joseph M.,Buchwald, Stephen L.. "An Improved Synthesis of Functionalized Biphenyl-Based Phosphine Ligands". . p. 5334 - 5341. Retrieved 2007/10/03.