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Sigma-Aldrich

(S)-(+)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate

97%

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Synonym(s):
(S)-(+)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate, (S)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide
Empirical Formula (Hill Notation):
C20H13O4P
CAS Number:
35193-64-7
Molecular Weight:
348.29
Beilstein:
4787775
MDL number:
MFCD00010045
PubChem Substance ID:
24854963
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

optical activity

[α]22/D +595°, c = 1.35 in methanol

SMILES string

OP1(=O)Oc2ccc3ccccc3c2-c4c(O1)ccc5ccccc45

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

Used as a chiral Bronsted acid catalyst in the enantoselective Mannich reaction.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Precautionary Statements

P302 + P352

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Yingying Dong et al.
Electrophoresis, 32(13), 1735-1741 (2011-06-28)
Gels formed by self-association of monomeric guanosine compounds join numerous other agents such as cyclodextrins, crown ethers, chiral surfactants, antibiotics, proteins, and polysaccharides for chiral separations. Guanosine gels (G-gels) are self-assembled networks of hydrogen-bonded tetrads formed by guanosine nucleotides and
Anna Bielejewska et al.
Journal of chromatography. A, 977(2), 225-237 (2002-11-29)
The chiral recognition ability of single and dual selectors, that were used as additives, have been investigated by HPLC and CE. Native beta- and gamma-cyclodextrins, permethylated beta-cyclodextrin, hydroxypropyl-beta-cyclodextrin, cholic acid and taurodeoxycholic acid sodium salts were applied as chiral selectors
Stephanie A Kingsbury et al.
Magnetic resonance in chemistry : MRC, 48(3), 184-191 (2010-01-06)
NMR spectroscopy was used to characterize the binding of the chiral compound 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (BNP) to five molecular micelles with chiral dipeptide headgroups. Molecular micelles have covalent linkages between the surfactant monomers and are used as chiral mobile phase
Ioannis J Stavrou et al.
Electrophoresis, 34(4), 524-530 (2012-12-05)
In this study, the applicability of a chiral ionic liquid (CIL) as the sole chiral selector in CE was investigated for the first time. In particular, five amino acid ester-based CILs were synthesized and used as additives in the BGE
Ulrich Schmitt et al.
Electrophoresis, 25(16), 2801-2807 (2004-09-08)
Comparative enantioseparation of the enantiomers of 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate was performed with cyclodextrin (CD)-modified capillary electrophoresis (CE). Two single isomers, beta-CD, heptakis(2,3,6-tri-O-methyl)-beta-CD (TM-beta-CD), and heptakis(2,6-di-O-methyl)-beta-CD (DM-beta-CD) of 98% purity as well as heptakis(2,3-di-O-acetyl)-beta-CD were used and compared in terms of
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