Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

675512

Sigma-Aldrich

(R)-(–)-VAPOL hydrogenphosphate

Synonym(s):

(R)-2,2′-Diphenyl-3,3′-biphenanthryl-4,4′-diyl phosphate, (R)-VAPOL phosphoric acid, 18-Hydroxy-8,9-diphenyl-diphenanthro[4,3-d:3′,4′-f][1,3,2]dioxaphosphepin-18-oxide

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

About This Item

Empirical Formula (Hill Notation):
C40H25O4P
CAS Number:
871130-18-6
Molecular Weight:
600.60
MDL number:
MFCD09265084
UNSPSC Code:
12352005
PubChem Substance ID:
24885284
NACRES:
NA.22

form

solid

SMILES string

OP1(=O)Oc2c(c(cc3ccc4ccccc4c23)-c5ccccc5)-c6c(O1)c7c(ccc8ccccc78)cc6-c9ccccc9

InChI

1S/C40H25O4P/c41-45(42)43-39-35-29(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)44-45/h1-24H,(H,41,42)

InChI key

YKIJNEDTUDPMNC-UHFFFAOYSA-N

Application

Catalyst involved in:
  • Desymmetrization of meso-aziridines
  • Asymmetric aza-Darzens aziridine synthesis
  • Enantioselective ring-opening of mono-and bicyclic N-acyl meso aziridines
  • Condensation of aldehydes with amino benzenesulfonamides
  • Pictet-Spengler reactions
Useful chiral Bronsted acid catalyst in the addition of sulfonamides to Boc-activated aryl imines.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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?

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

Visit the Document Library

Gerald B Rowland et al.
Journal of the American Chemical Society, 127(45), 15696-15697 (2005-11-10)
A new method for the Brønsted acid-catalyzed addition of amide nucleophiles to imines to produce protected aminal products is described. Simple Brønsted acids (phenyl phosphinic acid and trifluoromethanesulfonimide) were shown to be excellent catalysts, providing high yields of the aminal

Articles

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