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(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate

(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate

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Catalog Number

ACM39648674

Product Name

Structure

CAS

39648-67-4

Product Overview
Usage
Reviews

Synonyms

(R)-(-)-1,1'-BINAPHTHALENE-2,2'-DIYL-PHOSPHATE; 4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide; (R)-5,5 inverted exclamation mark ,6,6 inverted exclamation mark ,7,7 inverted exclamation mark ,8,8 inverted exclamation mark -Octahydro-1,1 inverted exclamation mark -binaphthyl-2,2 inverted exclamation mark -diyl hydrogen phosphate; -Binaphthyl-2,2; dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-ol 4-oxide; NSC244999; FT-0605235; (+)-4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide; O732; SC-04178;

IUPAC Name

13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 13-oxide;

Molecular Weight

348.294g/mol

Molecular Formula

C20H13O4P;

Canonical SMILES

C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC5=CC=CC=C54)OP(=O)(O3)O;

InChI

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;

Storage

Refrigerator

Complexity

508

Covalently-Bonded Unit Count

EC Number

609-734-1

Exact Mass

348.055g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

348.055g/mol

NSC Number

244999

Topological Polar Surface Area

55.8A^2

Application

(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate serves as a versatile chiral ligand employed in various asymmetric synthesis applications. It is especially effective in hydrocarboxylation reactions where it complexes with rhodium, and it facilitates the asymmetric dipolar cycloaddition of diazo compounds. As an acidic resolving agent, it proficiently separates certain racemic amines that are challenging to resolve. This compound also acts as a chiral quenching agent and plays a crucial role in catalyzing asymmetric hetero Diels-Alder reactions using chiral lanthanide(III) complexes. Additionally, it enhances the efficiency of the Mannich reaction. Its utility extends to forming palladium derivatives for asymmetric hydrocarboxylations and rhodium derivatives for dipolar cycloadditions.

March 30, 2025

Exceptional Chiral Ligand for Research Applications

The (R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate from Alfa Chemistry proved invaluable in our lab. It excels in asymmetric Diels-Alder reactions and efficiently resolves complex racemic amine mixtures. Ideal for enhancing research outcomes.

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