MilliporeSigma
All Photos(1)

Documents

676098

Sigma-Aldrich

(S)-VANOL

97%

Sign Into View Organizational & Contract Pricing

Synonym(s):
(S)-3,3′-Diphenyl-2,2′-bi(1-naphthalol), (S)-3,3′-Diphenyl-2,2′-bi-(1-naphthol)
Empirical Formula (Hill Notation):
C32H22O2
CAS Number:
Molecular Weight:
438.52
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

optical activity

[α]20/D -314°, c = 1 in chloroform

mp

199-203 °C

SMILES string

Oc1c(c(cc2ccccc12)-c3ccccc3)-c4c(O)c5ccccc5cc4-c6ccccc6

InChI

1S/C32H22O2/c33-31-25-17-9-7-15-23(25)19-27(21-11-3-1-4-12-21)29(31)30-28(22-13-5-2-6-14-22)20-24-16-8-10-18-26(24)32(30)34/h1-20,33-34H

InChI key

NDTDVKKGYBULHF-UHFFFAOYSA-N

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
675156595721693014
(S)-VANOL 97%

676098

(S)-VANOL

(R)-VANOL 97%

675156

(R)-VANOL

(S)-H8-BINAP technical grade

693014

(S)-H8-BINAP

mp

199-203 °C

mp

200-204 °C

mp

256-260 °C

mp

-

optical activity

[α]20/D -314°, c = 1 in chloroform

optical activity

[α]20/D +310°, c = 1 in chloroform

optical activity

-

optical activity

-

Application

(S)-VANOL is a vaulted biaryl ligand that may be used in the synthesis of coordinated complexes, such as (dppe)Pt(S-VANOL) [dppe= bis(diphenylphosphino)ethane] and (S,S-chiraphos)Pt(S-VANOL) [chiraphos= 2,3-bis(diphenylphosphino)butane].
VANOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Aquatic Chronic 4 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Synthesis and characterization of chiral diphosphine platinum (II) VANOL and VAPOL complexes.
Becker JJ, et al.
Organometallics, 22(16), 3245-3249 (2003)
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
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.

Related Content

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