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Merck
CN

675512

(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

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About This Item

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

Key Documents

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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)

SMILES string

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

InChI key

YKIJNEDTUDPMNC-UHFFFAOYSA-N

form

solid

Quality Level

100

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBW0706V
MKBJ7505V
01617HJ
00625HJ
10018AJ

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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

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