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675210

Sigma-Aldrich

(R)-VAPOL

97%

Synonym(s):

(R)-2,2′-Diphenyl-3,3′-(4-biphenanthrol)

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About This Item

Empirical Formula (Hill Notation):
C40H26O2
CAS Number:
147702-16-7
Molecular Weight:
538.63
MDL number:
MFCD11617354
UNSPSC Code:
12352005
PubChem Substance ID:
24885269
NACRES:
NA.22

Quality Level

100

Assay

97%

optical activity

[α]20/D -144°, c = 1 in chloroform

mp

225-229 °C

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.

Signal Word

Danger

Hazard Statements

H315 - H318 - H335 - H351

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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.

EU REACH Annex XVII (Restriction List)

CAS No.

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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

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