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676098

Sigma-Aldrich

(S)-VANOL

97%

Synonym(s):

(S)-3,3′-Diphenyl-2,2′-bi(1-naphthalol), (S)-3,3′-Diphenyl-2,2′-bi-(1-naphthol)

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About This Item

Empirical Formula (Hill Notation):
C32H22O2
CAS Number:
147702-14-5
Molecular Weight:
438.52
MDL number:
MFCD08459338
UNSPSC Code:
12352005
PubChem Substance ID:
24884836
NACRES:
NA.22

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

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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335,H413

Hazard Classifications

Aquatic Chronic 4 - 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

Personal Protective Equipment

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’.

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(R)-(+)-1,1′-Bi(2-naphthol) 99%

Sigma-Aldrich

246948

(R)-(+)-1,1′-Bi(2-naphthol)

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