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650870

Sigma-Aldrich

(S)-BINAPINE

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Synonym(s):
(3S,3’S,4S,4’S,11bS,11’bS)-(+)-4,4′-Di-t-butyl-4,4′,5,5′-tetrahydro-3,3′-bi-3H-dinaphtho[2,1-c:1′,2′-e]phosphepin
Empirical Formula (Hill Notation):
C52H48P2
CAS Number:
528854-26-4
Molecular Weight:
734.89
MDL number:
MFCD06658119
UNSPSC Code:
12352005
PubChem Substance ID:
24883786

form

solid

mp

>300 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)P1Cc2ccc3ccccc3c2-c4c(ccc5ccccc45)[C@H]1[C@H]6P(Cc7ccc8ccccc8c7-c9c6ccc%10ccccc9%10)C(C)(C)C

InChI

1S/C52H48P2/c1-51(2,3)53-31-37-25-23-33-15-7-11-19-39(33)45(37)47-41-21-13-9-17-35(41)27-29-43(47)49(53)50-44-30-28-36-18-10-14-22-42(36)48(44)46-38(32-54(50)52(4,5)6)26-24-34-16-8-12-20-40(34)46/h7-30,49-50H,31-32H2,1-6H3/t49-,50-,53?,54?/m0/s1

InChI key

YXMFQIWDFKIXGQ-KUSQLHRJSA-N

Application

Chiral Quest Phosphine Ligands for Asymmetric Hydrogenation
Demonstates excellent enantioselectivity and reactivity for the asymmetric hydrogenation of Z-β-aryl(β-acylamino)acrylates.

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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A bisphosphepine ligand with stereogenic phosphorus centers for the practical synthesis of beta-aryl-beta-amino acids by asymmetric hydrogenation.
Wenjun Tang et al.
Angewandte Chemie (International ed. in English), 42(30), 3509-3511 (2003-08-06)

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