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

Base Information

• Chemical Name: 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
• CAS No.: 98327-87-8
• Molecular Formula: C₄₄H₃₂P₂
• Molecular Weight: 622.686
• Hs Code.: 29319090
• 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: 98327-87-8.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 beige powder
• Melting Point: 283-286 °C(lit.)
• Boiling Point: 724.3 °C at 760 mmHg
• Flash Point: 419 °C
• PSA: 27.18000
• LogP: 10.92580
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly, Sonicated), Dichloromethane (Slightly, Heated),
• Water Solubility.: Soluble in tetrahydrofuran, benzene and dichloromethane. Slightly soluble in ether, methanol and ethanol. Insoluble in water.
• 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:

99%+ ^*data from raw suppliers

2,2''-Bis(diphenylphosphino)-1,1''-dinaphthalene ^*data from reagent suppliers

Safty Information:

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

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: racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl ( (+/-)-BINAP ) is an essential role in the organic synthesis of enantioselective transformations catalyzed by the complexes of ruthenium, rhodium and palladium. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines. used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins. (^+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl plays an essential role in the organic synthesis of enantioselective transformations catalyzed by the complexes of ruthenium, rhodium and palladium. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines. It is used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins. 2,2'-Bis(diphenylphosphino)-1,1'-dinaphthalene is a powerful chiral auxiliary that is used as a homogeneous catalyst in some asymmetric chemical syntheses. 2,2'-Bis(diphenylphosphino)-1,1'-dinaphthalene is utilized for its high enantioselectivity and is used as a ligand to create coordination complexes.

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:

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

(S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide)

2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene

ethyl 2-(morpholin-4-yl)-benzoate

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.