(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate, 98+%, Thermo Scientific Chemicals

(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate is 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. Used in a chiral Bronsted acid catalyzed enantoselective Mannich reaction.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
(R)-(-)-1,1′-Binaphthyl-2,2′-diyl hydrogen phosphate is 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. Used in a chiral Bronsted acid catalyzed enantoselective Mannich reaction.

Solubility
Solubility in hot Methanol, almost transparency.

Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from oxidizing agents.

Chemical Identifiers

CAS

39648-67-4

Molecular Formula

C20H12O4P

Molecular Weight (g/mol)

347.29

MDL Number

MFCD00010045

InChI Key

JEHUZVBIUCAMRZ-UHFFFAOYSA-M

Synonym

1,1'-binaphthyl-2,2'-diyl hydrogenphosphate, s-+-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate, r---1,1'-binaphthyl-2,2'-diyl hydrogenphosphate, 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, r---bnp acid, 11bs-4-hydroxydinaphtho 2,1-d:1',2'-f 1,3,2 dioxaphosphepine 4-oxide, r---1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, r-4-hydroxydinaphtho 2,1-d:1',2'-f 1,3,2 dioxaphosphepine 4-oxide, s-+-bnp acid, 4-hydroxydinaphtho 2,1-d:1',2'-f 1,3,2 dioxaphosphepine 4-oxide

PubChem CID

99589

IUPAC Name

13-oxo-12,14-dioxa-13λ⁵-phosphapentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-olate

SMILES

[O-]P1(=O)OC2=CC=C3C=CC=CC3=C2C2=C3C=CC=CC3=CC=C2O1

Melting Point

>300°C

Quantity

250 mg

Beilstein

4713363

Optical Rotation

−605° (c=1 in Methanol)

Formula Weight

348.29

Percent Purity

≥98%

Chemical Name or Material

(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate

Hazard Category

H302+H312+H332-H315-H319-H335

Hazard Statement

GHS H Statement
H315-H319-H335
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.

Precautionary Statement

P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P362-P501c

DOTInformation

Hazard Class: 6.1; Packaging Group: III

TSCA

No

Recommended Storage

Ambient temperatures

SDS

Hazard Category

H302+H312+H332-H315-H319-H335

Hazard Statement

GHS H Statement
H315-H319-H335
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.

Precautionary Statement

P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P362-P501c

DOTInformation

Hazard Class: 6.1; Packaging Group: III

TSCA

No

Recommended Storage

Ambient temperatures

SDS

RUO – Research Use Only