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Merck
CN

693537

R-MOP

≥94%

Synonym(s):

(R)-(+)-2-(Diphenylphosphino)-2′-methoxy-1,1′-binaphthyl

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About This Item

Empirical Formula (Hill Notation):
C33H25OP
CAS Number:
145964-33-6
Molecular Weight:
468.52
UNSPSC Code:
12352005
PubChem Substance ID:
329761598
MDL number:
MFCD00269686

Key Documents

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Product Name

R-MOP, ≥94%

InChI

1S/C33H25OP/c1-34-30-22-20-24-12-8-10-18-28(24)32(30)33-29-19-11-9-13-25(29)21-23-31(33)35(26-14-4-2-5-15-26)27-16-6-3-7-17-27/h2-23H,1H3

SMILES string

COc1ccc2ccccc2c1-c3c(ccc4ccccc34)P(c5ccccc5)c6ccccc6

InChI key

KRWTWSSMURUMDE-UHFFFAOYSA-N

assay

≥94%

form

solid

optical activity

[α]20/D +94°, c = 0.5 in chloroform

Application

Takasago Ligands and Complexes for Asymmetric Reactions

Ligand used in palladium-catalyzed asymmetric hydrosilylation of olefins, palladium-catalyzed reduction of allylic esters, rhodium-catalyzed asymmetric addition reactions, and asymmetric amination reactions catalyzed by copper(I) complexes.

General description

R-MOP is a phosphine ligand with a bis-naphthalene backbone.

Legal Information

Sold in collaboration with Takasago for research purposes only. US5231202

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBJ0441V
03502EJ
02704MH

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Gaku Hattori et al.
Journal of the American Chemical Society, 132(30), 10592-10608 (2010-07-14)
The scope and limitations of the copper-catalyzed propargylic amination of various propargylic esters with amines are presented, where optically active diphosphines such as Cl-MeO-BIPHEP and BINAP work as good chiral ligands. A variety of secondary amines are available as nucleophiles
T Hayashi
Accounts of chemical research, 33(6), 354-362 (2000-07-13)
Chiral monophosphines, whose chirality is due to biaryl axial chirality, have been prepared from enantiomerically pure 2, 2'-dihydroxy-1,1'-binaphthyl and demonstrated to be highly efficient chiral ligands for transition-metal-catalyzed organic transformations, especially for reactions where chelating bisphosphine ligands cannot be used.
The synthesis of P-stereogenic MOP analogues and their use in rhodium catalyzed asymmetric addition
Clarke, E. F.; et al.
Journal of Organometallic Chemistry, 696, 3608-3615 (2011)
Uozomi, Y.
Journal of the American Chemical Society, 9887-9887 (1991)
A new optically active monodentate phosphine ligand, (R)-(+)-3-diphenylphosphino-3'-methoxy-4,4'-biphenanthryl (MOP-phen): preparation and use for palladium-catalyzed asymmetric reduction of allylic esters with formic acid
Hayashi, T.
Synthesis, 526-532 (1994)
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Articles

Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

Chiral Diene Ligands for Asymmetric Transformations

Chiral diene ligands enable asymmetric transformations, constructing enantioenriched compounds from achiral substrates efficiently.

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