248932
(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate
≥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:
Molecular Weight:
348.29
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Beilstein/REAXYS Number:
4713363
MDL number:
Quality Segment
assay
≥98%
form
solid
optical activity
[α]20/D −605°, c = 1.35 in methanol
reaction suitability
reagent type: chrial catalyst
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
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.
Signal Word
Warning
Hazard Codes
Precautionary Statements
Hazard Classifications
Skin Irrit. 2
Storage Class
11 - Combustible Solids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
PPE (personal protective equipment)
dust mask type N95 (US), Eyeshields, Gloves
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