2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl

Base Information

• Chemical Name: 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl
• CAS No.: 564483-19-8
• Molecular Formula: C29H45P
• Molecular Weight: 424.65
• Hs Code.: 29310099
• Mol file: 564483-19-8.mol

Synonyms:Phosphine, bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]-;

Chemical Property of 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl

Chemical Property:

• Melting Point: 148-151 °C(lit.)
• Boiling Point: 493.479ºC at 760 mmHg
• Flash Point: 267.742ºC
• PSA: 13.59000
• LogP: 9.42800
• Solubility.: soluble in Toluene

Purity/Quality:

98% ^*data from raw suppliers

Di-tert-butyl(2'',4'',6''-triisopropyl-[1,1''-biphenyl]-2-yl)phosphine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: tBuXPhos?[2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions. tBuXPhos has been used in the preparation of [tBuXPhosAu(MeCN)]BAr4F, a gold catalyst for the intermolecular [2+2] cycloaddition of terminal arylalkynes with substituted alkenes to form functionalized cyclobutenes with high regioselectivity. tBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation. It can be used in the following reactions: ??Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides. ??Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides. ??Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones. Effective ligand for the Pd-catalyzed arylation of pyrazoles, indazoles and amino heterocycles tBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation.It can be used in the following reactions:Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones. suzuki reaction

Technology Process of 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl

There total 2 articles about 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl 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: 94.0%

di(tert-butyl)chlorophosphine (13716-10-4) + 2-bromo-1-chlorobenzene (694-80-4) + 2,4,6-triisopropyl-1-bromobenzene (21524-34-5) → tert-butyl XPhos (564483-19-8)

Guidance literature:

2-bromo-1-chlorobenzene; 2,4,6-triisopropyl-1-bromobenzene; With magnesium; In tetrahydrofuran; for 2h; Inert atmosphere; Reflux;

di(tert-butyl)chlorophosphine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 5.5h; Reagent/catalyst; Reflux; Inert atmosphere;

Reference yield: 86.0%

di-tert-butylphosphine (819-19-2) + 2,4,6-triisopropylphenylboronic acid (154549-38-9) + 2,3-dibromobenzene (583-53-9) → tert-butyl XPhos (564483-19-8)

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 8h; Inert atmosphere;

2,4,6-triisopropylphenylboronic acid; In toluene; at 100 ℃; for 12h; Inert atmosphere;

Reference yield: 87.0%

bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II) (225931-80-6) + p-trifluoromethylphenyl bromide (402-43-7) + tert-butyl XPhos (564483-19-8) → (t-BuXPhos)Pd[(4-CF3)Ph]Br

Guidance literature:

In pentane; at 20 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.1c02101

upstream raw materials:

di(tert-butyl)chlorophosphine

2-bromo-1-chlorobenzene

2,4,6-triisopropyl-1-bromobenzene

di-tert-butylphosphine

Downstream raw materials:

tert-butyl 2-(benzamido)-4-(3-methoxyphenoxy)benzoate

tert-butyl 2-(benzamido)-4-(3-nitrophenoxy)benzoate

tert-butyl 2-(benzamido)-4-(3,5-difluorophenoxy)benzoate

tert-butyl 2-(benzamido)-4-(4-methylphenoxy)benzoate

Refernces

• 1、 -. "A preparation method of compound phosphine benzene apperception (by machine translation)". Paragraph 0078; 0079; 0080; 0081. . Retrieved 2016/11/14.