2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

Base Information

• Chemical Name: 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
• CAS No.: 76189-56-5
• Molecular Formula: C₄₄H₃₂P₂
• Molecular Weight: 622.686
• Hs Code.: HOSPHINO)-1,1'-BINAPHTHYL PRODUCT IDENTIFICATION
• European Community (EC) Number: 616-304-7,616-305-2,619-338-0,918-620-3
• UNII: 4F1X2F8NA3,OX12238KWH,970O8508MB
• DSSTox Substance ID: DTXSID40913327
• Nikkaji Number: J1.058.033A,J1.058.045E,J181.354D,J181.355B,J461.407K
• Wikipedia: BINAP
• Wikidata: Q795991,Q98000133,Q72445368
• ChEMBL ID: CHEMBL1275990
• Mol file: 76189-56-5.mol

Synonyms:(S)-BINAP;BINAP;BINAP, 2-naphthol;BINOLAM

Chemical Property of 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 283-286 °C(lit.)
• Refractive Index: -235 ° (C=0.3, Toluene)
• Boiling Point: 724.3 °C at 760 mmHg
• Flash Point: 419 °C
• PSA: 27.18000
• LogP: 9.17640
• Storage Temp.: Room temperature.
• Sensitive.: Air Sensitive
• Solubility.: Benzene (Slightly), Chloroform (Slightly)
• XLogP3: 11.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 622.19792502
• Heavy Atom Count: 46
• Complexity: 797

Purity/Quality:

98%, ^*data from raw suppliers

(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
• Uses: Reactant involved in:Enantioselective and diastereoselective unpoled carbonyl allylationSyntehsis of organophophine oxides as anittumor agentsSN2 halogenation of hydroxy groupsSynthesis of BINAP complexesStudies of conformational flexibility of BINAP chelates 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.Ligand used in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process leading to a synthesis of a tricyclic sesquiterpene. Also used in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids.

Technology Process of 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

There total 49 articles about 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 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: 98.4%

2,2'-dibromo-1,1'-binaphthyl (74866-28-7,86688-08-6,150024-49-0) + diphenylphosphonium chloride → 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl (76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8)

Guidance literature:

2,2'-dibromo-1,1'-binaphthyl; With magnesium; In tetrahydrofuran; at 70 ℃; for 0.5h; Inert atmosphere; Large scale;

diphenylphosphonium chloride; In tetrahydrofuran; at -10 - 20 ℃; for 2h; Temperature; Large scale;

Reference yield: 97.0%

(R)-2,2'-diethoxy-1,1'-binaphthyl (19491-17-9,109135-26-4,109135-27-5) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl (76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8)

Guidance literature:

(R)-2,2'-diethoxy-1,1'-binaphthyl; With N,N,N,N,-tetramethylethylenediamine; lithium; In tetrahydrofuran; at 65 ℃; for 10h; Large scale;

chloro-diphenylphosphine; In tetrahydrofuran; at 0 ℃; Reagent/catalyst; Temperature; Solvent; Large scale;

Reference yield: 95.0%

2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene (130164-89-5,94041-16-4,94041-18-6,86632-33-9) → 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl (76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8)

Guidance literature:

With trichlorosilane; triethyl phosphite; In tetrahydrofuran; toluene; at 100 ℃; for 3h;

DOI:10.1021/ol048227c

upstream raw materials:

2,2'-dibromo-1,1'-binaphthyl

chloro-diphenylphosphine

diphenylarsane

(+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl

Downstream raw materials:

N-tert-butylaniline

N-(3,5-dimethylphenyl)-tert-butylamine

(R)-2,2’-bis(1,1-diphenyl-1,1’-phosphine oxide)-1,1’-binaphthyl

Refernces

• 1、 Ye, Jing-Jing,Zhang, Jian-Qiu,Shimada, Shigeru,Han, Li-Biao. "One-pot synthesis of binaphthyl-based phosphines via direct modification of BINAP". supporting information. . Retrieved 2021/11/18.
• 2、 -. "Synthetic method of 2,2'-double diphenyl phosphine-1,1'-dinaphthalene". Paragraph 0018; 0033; 0034. . Retrieved 2018/10/11.