248932
(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate
≥98%
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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
Empirical Formula (Hill Notation):
C20H13O4P
CAS Number:
Molecular Weight:
348.29
Beilstein:
4713363
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
![(R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate 95%](/deepweb/assets/sigmaaldrich/product/structures/270/636/14dc9413-bcb4-478c-8e4d-3605317c13a5/640/14dc9413-bcb4-478c-8e4d-3605317c13a5.png)
Quality Level
Assay
≥98%
form
solid
optical activity
[α]20/D −605°, c = 1.35 in methanol
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
Related Categories
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Irrit. 2
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Find documentation for the products that you have recently purchased in the Document Library.
Tetrahedron Letters, 33, 5987-5987 (1992)
Craig, J.C. Ansari, A.M.
Chirality, 5, 188-188 (1993)
Controlled ring-opening polymerization of cyclic esters with phosphoric acid as catalysts
Zhou Xi and Hong L
Colloid and Polymer Science, 291(9), 2155-2162 (2013)
Organophosphate-accelerated copper-catalyzed C (sp2)-C (sp) Sonogashira-type cross couplings
Xu W, et al.
Applied Organometallic Chemistry, 29(5), 301-304 (2015)
Pirrung, M.C. Zhang, J.
Tetrahedron Letters, 33, 5987-5987 (1992)
Articles
TRIP and TiPSY Chiral Phosphoric Acid Catalysts
Chromatograms
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