1.1'-Binaphthyl-2.2'-diphemyl phosphine Chemical Properties

Melting point:

283-286 °C(lit.)

Boiling point:

724.3±55.0 °C(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly, Sonicated), Dichloromethane (Slightly, Heated),

form 

Powder

color 

White to light beige

Water Solubility 

Soluble in tetrahydrofuran, benzene and dichloromethane. Slightly soluble in ether, methanol and ethanol. Insoluble in water.

Sensitive 

Air Sensitive

Merck 

14,1223

BRN 

5321443

InChIKey

MUALRAIOVNYAIW-UHFFFAOYSA-N

CAS DataBase Reference

98327-87-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

F 

8-10-23

TSCA 

No

HS Code 

29319090

MSDS

• Language:English Provider:2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1.1'-Binaphthyl-2.2'-diphemyl phosphine Usage And Synthesis

Chemical Properties

1.1'-Binaphthyl-2.2'-diphemyl phosphine is White to light beige powder

Uses

1. 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.
2. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines.
3. used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins.

Uses

(^+)-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.

Uses

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.

Reactions

Phosphine Ligand Kit component.

1. Useful ligand for palladium-catalyzed carbon-nitrogen bond formation.
2. Useful ligand for rhodium-catalyzed C-C bond formation.
3. Useful ligand for palladium-catalyzed intramolecular acylation of aryl bromides via C-H activation.
4. Used in the preparation of Buchwald third generation precatalyst.
5. Used in methoxy directed Rhodium migration.
6. Used in Nickel catalyzed C-N cross-coupling reactions.
   

General Description

Racemic version of BINAP.

Purification Methods

Dissolve the enantiomer in toluene, wash it with 30% aqueous NaOH, three times with H2O, dry (Na2SO4), evaporate to ~15% of its volume and add an equal volume of degassed MeOH. Collect the solid, wash it with MeOH and dry it at 80o/0.005mm for 6hours. Recrystallise it from a 1:1 mixture of toluene/EtOH to optical purity (m 241-242o) [Takaya et al. Org Synth 67 20 1989]. [Noyori & Takaya Acc Chem Res 2 3 345 1990, Kitamura et al. Org Synth 71 1 1993, Takaya et al. Org Synth 72 74 1995, Kitamura et al. J Org Chem 57 4053 1992.]

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