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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

Assay

97%

form

solid

optical activity

[α]22/D +595°, c = 1.35 in methanol

functional group

phosphate

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000360706
0000359398
0000320059
0000360706
0000359398

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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
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
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
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
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
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