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248940

Sigma-Aldrich

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

97%

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

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About This Item

Empirical Formula (Hill Notation):
C20H13O4P
CAS Number:
35193-64-7
Molecular Weight:
348.29
Beilstein:
4787775
MDL number:
MFCD00010045
UNSPSC Code:
12352005
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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Masahiro Yamanaka et al.
Journal of the American Chemical Society, 129(21), 6756-6764 (2007-05-05)
Mannich-type reaction of ketene silyl acetals with aldimines proceeded catalytically by means of a phosphoric acid diester, derived from (R)-BINOL, as a chiral Brønsted acid to afford beta-amino esters with good diastereoselectivity in favor of the syn isomer and high
Christine M Hebling et al.
Langmuir : the ACS journal of surfaces and colloids, 24(24), 13866-13874 (2008-12-05)
Bile salt micelles can be employed as a pseudostationary phase in micellar electrokinetic capillary chromatography (MEKC) separations of chiral analytes. To improve MEKC separations of chiral analytes, a molecular level understanding of micelle aggregation in the presence of analyte is
Fluorescence anisotropy as a measure of chiral recognition.
M E McCarroll et al.
Journal of the American Chemical Society, 123(13), 3173-3174 (2001-07-18)
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
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