Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

675334

Sigma-Aldrich

(S)-VAPOL

97%

Synonym(s):

(S)-2,2′-Diphenyl-(4-biphenanthrol)

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

About This Item

Empirical Formula (Hill Notation):
C40H26O2
CAS Number:
147702-15-6
Molecular Weight:
538.63
EC Number:
200-838-9
MDL number:
MFCD11617354
UNSPSC Code:
12352005
PubChem Substance ID:
24885273
NACRES:
NA.22

assay

97%

form

solid

optical activity

[α]20/D 128°, c = 1 in chloroform

mp

185-191 °C

functional group

phenyl

SMILES string

Oc1c(c(cc2ccc3ccccc3c12)-c4ccccc4)-c5c(O)c6c(ccc7ccccc67)cc5-c8ccccc8

InChI

1S/C40H26O2/c41-39-35-29(21-19-27-15-7-9-17-31(27)35)23-33(25-11-3-1-4-12-25)37(39)38-34(26-13-5-2-6-14-26)24-30-22-20-28-16-8-10-18-32(28)36(30)40(38)42/h1-24,41-42H

InChI key

UFYXKDMLGBKHIC-UHFFFAOYSA-N

Related Categories

Application

VAPOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBJ7879
MKBD1323
06128DJ
13605HE

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

Mariia Pushina et al.
Chemical communications (Cambridge, England), 55(31), 4495-4498 (2019-03-29)
The determination of enantiomeric excess (ee) in various groups of chiral compounds, namely amines, amino alcohols, diols, and hydroxy acids is performed using a dual chromophore FRET/PET based sensor ensemble. The sensing ensemble utilizes fluorescence changes from two chromophores (indicators)
Bao. J. et al.
Journal of the American Chemical Society, 118, 3392-3392 (1996)
Su Yu et al.
Organic letters, 7(3), 367-369 (2005-01-28)
[reaction: see text] In an effort to develop a synthesis of the VAPOL ligand that avoids the use of a chromium carbene complex, a route was examined that involved the annulation of a naphthalene carboxamide via the method of Snieckus.
Yu Zhang et al.
Organic letters, 5(11), 1813-1816 (2003-05-24)
[reaction: see text] A copper-mediated deracemization of the vaulted biaryl ligands VANOL and VAPOL can be readily achieved in the presence of (-)-spartiene. The optimal procedure involves the in situ generation of copper(II) and leads to the reproducible formation of

Related Content

Wulff Group – Professor Product Portal

The research areas of interest to the Wulff group include enantioselective catalysis, mechanisms of asymmetric catalysis, macromolecular chemistry, Fischer carbene complexes in organic synthesis and the total synthesis of natural products.

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