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682314

Sigma-Aldrich

(S)-N-Methyl-N-diphenylphosphino-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine

Synonym(s):

(1S)-1-(Diphenylphosphino)-2-[(1S)-1-[(diphenylphosphino)methylamino]ethyl]ferrocene, Methyl-BoPhoz

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About This Item

Empirical Formula (Hill Notation):
C37H35FeNP2
CAS Number:
406681-09-2
Molecular Weight:
611.47
MDL number:
MFCD05865220
UNSPSC Code:
12352005
PubChem Substance ID:
329760487

form

solid

mp

104.1-109.2 °C

functional group

amine
phosphine

SMILES string

[Fe].[CH]1[CH][CH][CH][CH]1.C[C@@H]([C]2[CH][CH][CH][C]2P(c3ccccc3)c4ccccc4)N(C)P(c5ccccc5)c6ccccc6

InChI

1S/C32H30NP2.C5H5.Fe/c1-26(33(2)35(29-20-11-5-12-21-29)30-22-13-6-14-23-30)31-24-15-25-32(31)34(27-16-7-3-8-17-27)28-18-9-4-10-19-28;1-2-4-5-3-1;/h3-26H,1-2H3;1-5H;/t26-;;/m1../s1

InChI key

ZIAZHUWEJYUGEO-FBHGDYMESA-N

Application

Methyl-BoPhoz can be used:
  • As an efficient ligand for asymmetric hydrogenation reactions.
  • To synthesize a single enantiomer of cyclopropylalanine via hydrogenation reaction using rhodium catalyst.
  • To prepare chiral phenylalanine derivatives from α-amido cinnamic acids (or esters) using rhodium catalyst.

Legal Information

Sold in collaboration with Johnson Matthey Catalyst for research purposes only. US6590115 and any patents arising therefrom apply.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCC9113
MKBG0559
01508EH

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Enantioselective Access to Chiral Drugs by using Asymmetric Hydrogenation Catalyzed by Rh (P-OP) Complexes
Etayo P, et al.
Chemistry?A European Journal , 17(50), 13978-13982 (2011)
Protecting-group-free synthesis of a dual CCK1/CCK2 receptor antagonist
Liu J, et al.
Organic & Biomolecular Chemistry, 9(8), 2654-2660 (2011)
The preparation of enantiomerically pure cyclopropylalanine.
Boaz NW, et al.
Tetrahedron Asymmetry, 14(22), 3575-3580 (2003)

Articles

P-Phos, PhanePhos and BoPhoz™ Ligands

P-Phos ligand family enhances catalysis, featuring atropisomeric biaryl bisphosphine with unique structural elements.

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