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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.[1][2]
  • To synthesize a single enantiomer of cyclopropylalanine via hydrogenation reaction using rhodium catalyst.[2]
  • To prepare chiral phenylalanine derivatives from α-amido cinnamic acids (or esters) using rhodium catalyst.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCC9113
MKBG0559
01508EH

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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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