Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000360706
0000359398
0000360706
0000359398
0000320059

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service