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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

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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

Quality Level

100

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

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.

JAN Code

675512-100MG:
675512-500MG:
675512-BULK:
675512-VAR:
675512-250MG:

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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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