Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

673986

Sigma-Aldrich

2,6-Bis[(3aR,8aS)-(+)-8H-indeno[1,2-d]oxazolin-2-yl)pyridine

≥94%

Synonym(s):

(3aR,3′aR,8aS,8′aS)-2,2′-(2,6-Pyridinediyl)bis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole, (3aR,8aS)-in-pybox

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C25H19N3O2
CAS Number:
357209-32-6
Molecular Weight:
393.44
MDL number:
MFCD09265074
UNSPSC Code:
12352005
PubChem Substance ID:
24885191
NACRES:
NA.22

Assay

≥94%

form

solid

optical activity

[α]20/D +386°, c = 1 in methylene chloride(lit.)

mp

284 °C (dec.)

SMILES string

C1[C@@H]2OC(=N[C@@H]2c3ccccc13)c4cccc(n4)C5=N[C@H]6[C@H](Cc7ccccc67)O5

InChI

1S/C25H19N3O2/c1-3-8-16-14(6-1)12-20-22(16)27-24(29-20)18-10-5-11-19(26-18)25-28-23-17-9-4-2-7-15(17)13-21(23)30-25/h1-11,20-23H,12-13H2/t20-,21-,22+,23+/m0/s1

InChI key

BZSJUFJXCHHRHW-MYDTUXCISA-N

Application

Catalytic ligand used for:
  • [3+2] cycloaddition of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavage
  • Enantioselective Mukaiyama-aldol reactions
  • Enantioselective carbonyl-ene reactions
  • Cu(I)-catalyzed asymmetric alkynylation of imino esters with terminal alkynes
  • Asymmetric three-component coupling reactions catalyzed by a Cu/pybox complex
  • Enantioselective Diels-Alder reaction
  • Ni-catalyzed cross-coupling reactions

Hazard Statements

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000297589
0000278973
BGBC2580V
MKBH2635V
MKBG7635V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Articles

PYBOX Ligand - Large Binding Site & Rigid Scaffold

The PYBOX ligand, consisting of a pyridine ring flanked by two oxazoline groups, was introduced in 1989 by Nishiyama.

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