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

Product no. chemwillR22BD11B91557

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R-BINAP 76189-55-4  (R)-(+)-BINAP

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Manufacturer High quality Best price In stock factory CAS 76189-55-4

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl CAS 76189-55-4

(R)-(+)-BINAP; (R)-BINAP; R-BINAP

Name:    (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
Synonyms:    (R)-(+)-2,2'-Bis(diphenylphosphino)-1;(+/-)-2,2'-Bis(diphenylphosphino)-1,1'-dinaphthalene (BINAP);(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-biphthyl;(R)-BINAP,99%e.e.;(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl for synthesis;(+/-)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE);(+/-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE;(+/-)-BINAP
CAS:    76189-55-4
MF:    C44H32P2
MW:    622.67
EINECS:    616-304-7
Product Categories:    BINAP Series;Chiral Phosphine;chiral;Biphenyl derivatives;Aromatics;Catalyst;Chiral Reagents;Asymmetric Synthesis;Phosphine Ligands;Synthetic Organic Chemistry;Adamantanes;B (Classes of Boron Compounds);Ligands;N-Heterocyclic Carbene Ligands;-;Tetrafluoroborates;Peptide;Chiral Compound
Mol File:    76189-55-4.mol
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Structure

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Chemical Properties

BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) is an organophosphorus compound. This chiral ligand is widely used in asymmetric synthesis. It consists of a pair of 2-diphenylphosphinonaphthyl groups linked at the 1 and 1´ positions. This C2-symmetric framework lacks a stereogenic atom, but has axial chirality due to restricted rotation (atropisomerism). The barrier to racemization is high due to steric hindrance, which limits rotation about the bond linking the naphthyl rings. The dihedral angle is approximately 90˚.

Appearance & Physical State     white to light yellow crystal powder
Boiling Point     724.3ºC at 760 mmHg
Melting Point     239-242ºC
Flash Point     419ºC
Refractive Index     235 ° (C=0.3, Toluene)
Water Solubility     insoluble
Storage Condition     Room temperature.
Safety Info
Safety Statements     S26-S37/39
HS Code     2902909090

Melting point     283-286 °C(lit.)
alpha     240 º (c=0.3, toluene)
refractive index     235 ° (C=0.3, Toluene)
storage temp.     Room temperature.
form     Powder
color     White to cream-white
optical activity    [α]20/D +222°, c = 0.5% in benzene
Water Solubility     insoluble

HS Code     29319090
MSDS Information

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Usage And Synthesis
Reaction    

    (R)-BINAP or (R)-Tol-BINAP can be combined with dichloro(1,5-cyclooctadiene)ruthenium to form precursors to NOYORI CATALYST SYSTEMS. These systems exhibit very high catalytic activity and enantioselectivity in the hydrogenation of a wide range of substrates. NOYORI CATALYST SYSTEMS have been shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydroxy, siloxy, carbonyl, ester, amide or thioester.

Chemical Properties    white to light yellow crystal powde
Uses    Chiral ligand for metal mediated asymmetric catalysis.
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Preparation Products And Raw materials
Raw materials    Etanol-->Ethyl acetate-->Methanol-->Dichloromethane-->N,N-Dimethylformamide-->Azabenzene-->Triphenylphosphine-->Trifluoroacetic anhydride-->Nickel(II) chloride hexahydrate-->Triethylenediamine-->1,2-Bis(diphenylphosphino)ethane-->(R)-(+)-1,1'-Bi-2-naphthol-->Diphenylphosphine
Preparation Products    (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one