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Safety Information

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

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

248940-5G:
248940-1G:
248940-VAR:
248940-250MG:
248940-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000360706
0000359398
0000320059
0000360706
0000359398

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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.
Journal of chromatography. A, 773(1-2), 331-338 (1997-06-27)
Selected water-soluble, native polysaccharides--such as amylose, laminaran, pullulan--and derivatized polysaccharides--methyl cellulose, hydroxypropyl cellulose, and carboxymethyl amylose sodium salt (CM-Am)--were investigated as chiral selectors in capillary electrophoresis. Effects of degree of polymerization and concentration of amylose on the separation of enantiomers
Dorothee Wistuba et al.
Electrophoresis, 27(21), 4359-4363 (2006-10-06)
Native delta-CD has been employed as chiral selector in CE and MEKC. To investigate the potential of the enantiodiscriminating properties of delta-CD, negatively charged 5-dimethylamino-1-naphthalene-sulfonyl (dansyl)-, 2,4-dinitrophenyl (DNP)- and FMOC-derivatives of several amino acids, 1,1'-binaphthyl-2,2'-diylhydrogenphosphate, flavanones and three positively charged
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
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