ChemicalBook Product Catalog Organic Chemistry Phosphines 1.1'-Binaphthyl-2.2'-diphemyl phosphine

1.1'-Binaphthyl-2.2'-diphemyl phosphine

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'-BINAPHTHYL;2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL;(+/-)-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)
CAS:98327-87-8
MF:C44H32P2
MW:622.69
EINECS:619-338-0
Product Categories:Achiral Phosphine;Aryl Phosphine;Phosphines;API intermediates;BINAP Series
Mol File:98327-87-8.mol
1.1'-Binaphthyl-2.2'-diphemyl phosphine Structure
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
InChIKeyMUALRAIOVNYAIW-UHFFFAOYSA-N
CAS DataBase Reference98327-87-8(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 Information
ProviderLanguage
2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl English
SigmaAldrich English
ACROS English
ALFA English
1.1'-Binaphthyl-2.2'-diphemyl phosphine Usage And Synthesis
Chemical Properties1.1'-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.
Uses2,2'-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.
ReactionsPhosphine 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.
    Reactions of 98327-87-8
General DescriptionRacemic version of BINAP.
Purification MethodsDissolve 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.]
(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE [(S)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II)CHLORIDE,[(S)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II)CHLORIDE BIS((R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1' -BINAPHTHYL)RHODIUM(I) PERCHLORATE, 96 1.1'-Binaphthyl-2.2'-diphemyl phosphine DICHLORO[(R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL][(R,R)-1,2-DIPHENYLETHANE DIAMINE]RUTHENIUM(II) DICHLORO[(R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL][(R)-1,1-BIS(P-METHOXYPHENYL)-2-ISOPROPYLETHANE-1,2-DIAMINE]RUTHENIUM(II) DICHLORO[(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL][(1S,2S)-(-)-1,2-DIPHENYLETHYLENEDIAMINE]RUTHENIUM (II) ((R)-(+)-2,2'-BIS(DIPHENYLPHOSPHIN)-1,1' -BINAPH)(1,5-CYCLOOCT)RH(I)CLO4/THF ADD Phenylphosphonic dichloride DICHLORO[(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM (II) DICHLORO[(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL][(1S,2S)-(-)-1,2-DIPHENYLETHYLENEDIAMINE]RUTHENIUM (II) [(S)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]BIS(2-METHYLALLYL)RUTHENIUM(II) Racemic-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl98327-87-8,Racemic-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl98327-87-8 N-(Carboxymethyl)-N-(phosphonomethyl)-glycine [(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE [(S)-(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL](1,5-CYCLOOCTADIENE)RHODIUM(I) PERCHLORATE [(R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]BIS(2-METHYLALLYL)RUTHENIUM(II)
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