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(R)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl (R)-MOP

(R)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl (R)-MOP - CAS 145964-33-6

(R)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl (R)-MOP is a chiral phosphine ligand for enantioselective synthesis with high yield and high enantioselective results.

Catalog Number

145964-33-6

CAS

145964-33-6

IUPAC Name

[1-(2-methoxynaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane

Synonyms

(R)-(+)-2-DIPHENYLPHOSPHINO-2'-METHOXY-1,1'-BINAPHTHYL; (S)-(-)-(DIPHENYLPHOSPHINO)-2'-METHOXY-1,1'-BINAPHTHYL; (R)-(+)-MOP; (R)-MOP; (S)-(-)-2-(DIPHENYLPHOSPHINO)-2'-METHOXY-1,1'-BINAPHTHYL; (S)-2-(DIPHENYLPHOSPHINO)-2'-METHOXY-1,1'-BINAPHTHYL

Molecular Weight

468.53

Molecular Formula

C33H25OP

Product Information

Canonical SMILES

COC1=C(C2=CC=CC=C2C=C1)C3=C(C=CC4=CC=CC=C43)P(C5=CC=CC=C5)C6=CC=CC=C6

InChI

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

Purity

95%

MDL

MFCD00269686

Physical State

Solid

Appearance

White to beige solid or powder

Storage

Inert atmosphere. Keep cold.

Boiling Point

584.1°C at 760 mmHg

Melting Point

177-179°C

Optical Activity

94° (c=0.3 in chloroform)

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P280 - P305 - P351 - P338

Hazard Statements

H317 - H319

Reference Reading

1.Syntheses and applications of 2-phosphino-2'-alkoxy-1,1'-binaphthyl ligands. Development of a working model for asymmetric induction in hydrovinylation reactions.

Saha B1, RajanBabu TV. J Org Chem. 2007 Mar 30;72(7):2357-63. Epub 2007 Mar 3.

Among the handful of monophosphine ligands that effect asymmetric hydrovinylation of vinylarenes, 2-diphenylphosphino-2'-methoxy-1,1'-binaphthyl (MOP) is among the most accessible. Addition of a methyl group at the 3'-position of this ligand significantly improves the enantioselectivity of hydrovinylation of prototypical alkenes. Introduction of a chiral phospholane at the C2 position of this scaffolding has no effect on the enantioselectivity. These results are consistent with a model proposed for the asymmetric induction for this exacting reaction.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass