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650854

(R)-BINAPHANE

Name: (<I>R</I>)-BINAPHANE
Brand: ALDRICH

Synonym(s):

(R,R)-1,2-Bis[(R)-4,5-dihydro-3H-binaphtho(1,2-c:2′,1′-e)phosphepino]benzene

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About This Item

Empirical Formula (Hill Notation):

C₅₀H₃₆P₂

CAS Number:

253311-88-5

Molecular Weight:

698.77

UNSPSC Code:

12352005

PubChem Substance ID:

24883783

MDL number:

MFCD06658114

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Properties

mp

>200 °C (dec.)

SMILES string

C1P(Cc2ccc3ccccc3c2-c4c1ccc5ccccc45)c6ccccc6P7Cc8ccc9ccccc9c8-c%10c(C7)ccc%11ccccc%10%11

InChI

1S/C50H36P2/c1-5-15-41-33(11-1)21-25-37-29-51(30-38-26-22-34-12-2-6-16-42(34)48(38)47(37)41)45-19-9-10-20-46(45)52-31-39-27-23-35-13-3-7-17-43(35)49(39)50-40(32-52)28-24-36-14-4-8-18-44(36)50/h1-28H,29-32H2

InChI key

CQYMOICHLLQQAH-UHFFFAOYSA-N

Description

Application

Chiral Quest Phosphine Ligands for Asymmetric Hydrogenation

Catalyst involved in:

Enantioselective anilinosulfonamide allyl alcohol cyclization
Synthesis of β-trifluoromethyl α-amino acids
Phosphine-catalyzed cycloadditions of aldehydes and ketoketenes
Dimerization of ketoketenes
Enantioselective carbonyl-ene reactions via palladium and platinum derivatives

(R)-Binaphane shows excellent enantioselectivity (up to >99% ee) for hydrogenation of E/Z-isomeric mixtures of β-substituted arylenamides.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

02545ED

02445ED

04411CD

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Synthesis of a novel chiral binaphthyl phospholane and its application in the highly enantioselective hydrogenation of enamides.

D Xiao et al.

Organic letters, 1(10), 1679-1681 (2000-06-03)

[formula: see text] A new chiral phosphine, (R,R)-1,2-bis[(R)-4,5-dihydro-3H-dinaphtho[2,1- c:1',2'-e]phosphepino]benzene [abbreviated as (R,R)-binaphane] was prepared on the basis of a practical route from a readily accessible enantiomerically pure binaphthanol. This ligand possesses both binaphthyl chirality and phospholane functionality. Excellent enantioselectivities (95-99.6%