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Merck
CN

650854

(R)-BINAPHANE

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
MDL number:
MFCD06658114
UNSPSC Code:
12352005
PubChem Substance ID:
24883783

Key Documents

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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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
02545ED
02445ED
04411CD

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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%

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