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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/REAXYS Number:
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

signalword

Warning

hcodes

H315

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

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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
B Chankvetadze et al.
Chirality, 10(1-2), 134-139 (1998-02-21)
Twelve different disaccharides and a series of noncyclic malto- and cello-oligosaccharides were used as chiral selectors in capillary electrophoresis (CE). Most saccharides resolved the enantiomers of atropisomeric 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (BDHP) depending on the type (alpha or beta) and position
Tom M H Choy et al.
Electrophoresis, 24(18), 3116-3123 (2003-10-01)
The feasibility of employing the "acetonitrile stacking" method in micellar electrokinetic chromatography (MEKC) for the on-line preconcentration and separation of enantiomers is demonstrated for the first time. The effects of various experimental parameters on the stacking and separation of three
Simon M Mwongela et al.
Journal of separation science, 30(9), 1334-1342 (2007-07-12)
In this study, we report the effects of adding ionic liquids (ILs), as compared to adding conventional molecular organic solvents (MOSs), to aqueous buffer solutions containing molecular micelles in the separation of chiral analyte mixtures in micellar EKC (MEKC). The
Y Mechref et al.
Electrophoresis, 18(6), 912-918 (1997-06-01)
Three alkylglycoside surfactants, namely n-octyl-beta-D-glucopyranoside (OG), n-nonyl-beta-D-glucopyranoside (NG), and n-octyl-beta-D-maltopyranoside (OM), were compared in the enantiomeric separation of dansyl amino acids, binaphthyl phosphate, bupivacaine and warfarin. While only OM exhibited an enantioselectivity toward warfarin, bupivacaine, and dansyl tryptophan, all three
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