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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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Protecting-group-free synthesis of a dual CCK1/CCK2 receptor antagonist
Liu J, et al.
Organic & Biomolecular Chemistry, 9(8), 2654-2660 (2011)
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)
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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