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Merck
CN

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:
39648-67-4
Molecular Weight:
348.29
UNSPSC Code:
12352005
PubChem Substance ID:
24854961
NACRES:
NA.22
Beilstein/REAXYS Number:
4713363
MDL number:
MFCD00010045

Key Documents

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Product Name

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate, ≥98%

assay

≥98%

form

solid

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

optical activity

[α]20/D −605°, c = 1.35 in methanol

functional group

phosphate

Quality Level

100

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315

Hazard Classifications

Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ5870
MKCC3039
MKBJ3949V
MKBC9251V
MKBC9251

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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)
Alper, H. Hamel, N.
Journal of the American Chemical Society, 112, 2803-2803 (1990)
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)
Tetrahedron Letters, 33, 5987-5987 (1992)
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