1.1'-Binaphthyl-2.2'-diphemyl phosphine CAS 98327-87-8

Introduction：Basic information about 1.1'-Binaphthyl-2.2'-diphemyl phosphine CAS 98327-87-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

1.1'-Binaphthyl-2.2'-diphemyl phosphine Basic information

• Product Name: 1.1'-Binaphthyl-2.2'-diphemyl phosphine
• Synonyms: (+/-)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE);(+/-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE;Racemic-2,2’-bis(diphenylphosphino)-1,1’-binaphthy;RACEMIC-2,2''-BIS(DIPHENYLPHOSPHINO)-1,1''-BINAPHTHYL BINAP;RAC-2,2''-BIS(DIPHENYLPHOSPHINO)-1,1''-BINAPHTHYL / RAC-BINAP;2,2'-Bis-(diphenylphosphino)-1,1'-binaphthyl (Racemic BINAP);(+/-)-2,2'-BIS-(DIPHENYLPHOSPHINO) -1,1'-BINAPHTHALINE PURISS;(BINAP) Racemic-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl
• CAS: 98327-87-8
• MF: C44H32P2
• MW: 622.69
• EINECS: 619-338-0
• Product Categories: Achiral Phosphine;Aryl Phosphine;BINAP Series;API intermediates;Phosphines
• Mol File: 98327-87-8.mol

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
• SMILES: P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC2=CC=CC=C2C=1C1C2=CC=CC=C2C=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1
• 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
• Storage Class: 11 - Combustible Solids

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.

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Acylations
reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-C Bond Formation
reagent type: ligand
reaction type: Decarboxylations
reagent type: ligand
reaction type: Stille Coupling

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.]

1.1'-Binaphthyl-2.2'-diphemyl phosphine Preparation Products And Raw materials

• Raw materials: Ethanol-->Ethyl acetate-->Methanol-->Dichloromethane-->N,N-Dimethylformamide-->Pyridine-->Triphenylphosphine-->Trifluoroacetic anhydride-->Nickel(II) chloride hexahydrate-->1,2-Bis(diphenylphosphino)ethane-->Triethylenediamine-->Diphenylphosphine-->1,1'-Bi-2-naphthol
• Preparation Products: 3-MORPHOLINOPHENYLBORONIC ACID PINACOL ESTER-->3-Morpholinobenzaldehyde-->3-MORPHOLINOPHENOL