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693537

Sigma-Aldrich

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
MDL number:
MFCD00269686
UNSPSC Code:
12352005
PubChem Substance ID:
329761598

Assay

≥94%

form

solid

optical activity

[α]20/D +94°, c = 0.5 in chloroform

SMILES string

COc1ccc2ccccc2c1-c3c(ccc4ccccc34)P(c5ccccc5)c6ccccc6

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

InChI key

KRWTWSSMURUMDE-UHFFFAOYSA-N

General description

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

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.

Legal Information

Sold in collaboration with Takasago for research purposes only. US5231202

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

693537-VAR:
693537-50MG:
693537-BULK:
693537-100MG:

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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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.
Uozomi, Y.
Journal of the American Chemical Society, 9887-9887 (1991)
Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins.
Ryo Shintani et al.
Angewandte Chemie (International ed. in English), 45(20), 3353-3356 (2006-04-06)
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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Takasago Ligands

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

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