(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate

Name: (<I>R</I>)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate
Brand: ALDRICH

≥98%

Synonym(s):

(R)-(−)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate, (R)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₁₃O₄P

CAS Number:

39648-67-4

Molecular Weight:

348.29

UNSPSC Code:

12352005

PubChem Substance ID:

24854961

NACRES:

NA.22

Beilstein/REAXYS Number:

4713363

MDL number:

MFCD00010045

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Properties

Quality Level

100

assay

≥98%

form

solid

optical activity

[α]20/D −605°, c = 1.35 in methanol

functional group

phosphate

SMILES string

[P]1(=O)(Oc2c(c5c(cc2)cccc5)c3c4c(ccc3O1)cccc4)O

InChI

1S/C20H13O4P/c21-25(22)23-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)24-25/h1-12H,(H,21,22)

InChI key

JEHUZVBIUCAMRZ-UHFFFAOYSA-N

Description

Application

A chiral ligand used in hydrocarboxylation reactions. Complexes with rhodium and mediates the asymmetric dipolar cycloaddition of diazo compounds. A number of racemic amines which have proven difficult to separate have been resolved with this chiral acid. Palladium derivatives have been used in asymmetric hydrocarboxylations, and rhodium derivatives have been used in dipolar cycloadditions.

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate is an organocatalyst that can be used:

To facilitates the controlled ring-opening homopolymerization and copolymerization of ε-caprolactone (cyclic ester).
As an additive along with a copper catalyst to achieve the highest catalytic activity in Sonogashira-type reactions.

Used in a chiral Bronsted acid catalyzed enantoselective Mannich reaction.