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About This Item
Empirical Formula (Hill Notation):
C20H13O4P
CAS Number:
Molecular Weight:
348.29
Beilstein/REAXYS Number:
4713363
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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
Application
(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.
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.
signalword
Warning
hcodes
Hazard Classifications
Skin Irrit. 2
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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