(S)-(+)-O-ANISYLMETHYLPHENYLPHOSPHINE BORANE

Base Information

• Chemical Name: (S)-(+)-O-ANISYLMETHYLPHENYLPHOSPHINE BORANE
• CAS No.: 97858-63-4
• Molecular Formula: C₁₄H₁₈BOP
• Molecular Weight: 244.081
• Mol file: 97858-63-4.mol

Synonyms:Boron,trihydro[(2-methoxyphenyl)methylphenylphosphine-P]-, [T-4-(S)]-; Phosphine,(2-methoxyphenyl)methylphenyl-, boron complex;(S)-(+)-o-Anisylmethylphenylphosphine borane

Chemical Property of (S)-(+)-O-ANISYLMETHYLPHENYLPHOSPHINE BORANE

Chemical Property:

• PSA: 19.04000
• LogP: 1.57380

Purity/Quality:

99%min ^*data from raw suppliers

(S)-(+)-O-ANISYLMETHYLPHENYLPHOSPHINE BORANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-(+)-O-ANISYLMETHYLPHENYLPHOSPHINE BORANE

There total 66 articles about (S)-(+)-O-ANISYLMETHYLPHENYLPHOSPHINE BORANE 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: 96.0%

(R(P))-(o-hydroxyphenyl)(methyl)(phenyl)phosphine-P-borane (917251-23-1,325153-84-2) + methyl iodide (74-88-4) → (R(P))-(o-anisyl)(methyl)(phenyl)phosphine-P-borane (129212-59-5,97764-41-5,97858-63-4)

Guidance literature:

With potassium carbonate; In acetone; at 50 ℃; for 3h;

DOI:10.1016/j.tetlet.2010.12.106

Reference yield: 91.0%

(+/-)-methylphenylphosphane borane (501381-03-9,119186-75-3,136172-50-4) + 4-iodoanisol (529-28-2) → (R(P))-(o-anisyl)(methyl)(phenyl)phosphine-P-borane (129212-59-5,97764-41-5,97858-63-4)

Guidance literature:

With dihydrogen peroxide; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; argon atmosphere; stirring (3 h, 70-80°C), addn. of water and H2O2 (room temp.), stirring (15 min); sepn. of org. layer, washing (aq. Na2S2O3, brine), drying (Na2SO4), isolation with preparative TLC;

DOI:10.1021/ja00169a036

Reference yield: 80.0%

2-bromoanisole (578-57-4) + (R)-(+)-(chloro)(methyl)phenylphosphine/borane complex → (S)-(+)-(o-anisyl)(methyl)phenylphosphine/borane complex (97764-41-5,97858-63-4,129212-59-5)

Guidance literature:

2-bromoanisole; With sec.-butyllithium; In cyclohexane; at 0 ℃; Inert atmosphere;

(R)-(+)-(chloro)(methyl)phenylphosphine/borane complex; In tetrahydrofuran; cyclohexane; toluene; at -78 - 20 ℃; for 1h; Inert atmosphere;

With water; In tetrahydrofuran; cyclohexane; at 0 ℃; Inert atmosphere;

DOI:10.1016/j.crci.2010.06.001

upstream raw materials:

methyl iodide

2-methoxyphenyllithium

(S)-(-)-methyl-(2-bromophenyl)phenylphosphinite borane

borane-THF

Downstream raw materials:

(R_p)-(2-methoxyphenyl)methylphenylphosphine oxide

(S_P,S_P)-1,2-bis[(o-anisyl)(phenyl)phosphino-P-borane]ethane

(S,S)-(-)-bis[(o-anisylphenylphosphinoborane)methylene]dimethylsilane

C₂₇H₃₂B₂O₂P₂

Refernces

• 1、 Song, Shu-Yong,Li, Yinwu,Ke, Zhuofeng,Xu, Senmiao. "Iridium-catalyzed enantioselective C-H borylation of diarylphosphinates". . p. 13445 - 13451. Retrieved 2021/11/16.
• 2、 Al Sulaimi, Sulaiman S.,Rajendran, Kamalraj V.,Gilheany, Declan G.. "Lithium Borohydride for Achiral and Stereospecific Reductive Boronation at Phosphorus: Lack of Electronic Effects on Stereoselective Formation of Alkoxyphosphonium Salts". supporting information. p. 5959 - 5965. Retrieved 2015/09/22.