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  • 683973 - (5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate

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683973 Sigma-Aldrich

(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate

93%

Synonym: Bode Catalyst 2

  • CAS Number 903571-02-8 (anhydrous)

  • Empirical Formula (Hill Notation) C21H22ClN3O · H2O

  • Molecular Weight 385.89

  •  PubChem Substance ID 329760886

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Other Organocatalysts
Quality Level   100
assay   93%
optical activity   [α]20/D +158°, c = 1 in chloroform
mp   226-230 °C
SMILES string   [Cl-].Cc1cc(C)c(c(C)c1)-[n+]2c[n@@H]3[C@@H]4[C@@H](Cc5ccccc45)OCc3n2
InChI   1S/C21H22N3O.ClH/c1-13-8-14(2)20(15(3)9-13)24-12-23-19(22-24)11-25-18-10-16-6-4-5-7-17(16)21(18)23;/h4-9,12,18,21H,10-11H2,1-3H3;1H/q+1;/p-1/t18-,21+;/m1./s1
InChI key   GUECWMLEUCWYOS-WKOQGQMTSA-M

Description

General description

It is an N-mesityl-substituted chiral triazolium N-heterocyclic carbene (NHC) compound. It was developed as an organocatalyst by the Bode group, for the catalytic generation of reactive species including activated carboxylates, homoenolates, and enolates.

Packaging

100 mg in clear glass bottle

250 mg in amber glass bottle

Legal Information

Sold in collaboration with BioBlocks, Inc.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Jeffrey Bode Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Jeffrey Bode Group – Professor Product Portal
Keywords: Annulations, Asymmetric synthesis, Catalysis, Cross couplings, transformation

N-Heterocyclic Carbene (NHC) Compounds

Rovis has demonstrated that triazolium salt (667080) in the presence of a base can act as an N-heterocyclic carbene organocatalyst1 in highly enantioselective intramolecular Stetter reactions.2 The S...
ChemFiles 2007, 7.9, 21.
Keywords: Addition reactions, Amidations, Annulations, Asymmetric synthesis, Catalysis, Esterifications, Stetter reaction

Shi Epoxidation Catalyst

This organocatalyst is able to epoxidize trans alkenes and certain cis alkenes with good to excellent yields and selectivities.
Aldrich ChemFiles 2007, 7.9, 22.
Keywords: Chemfiles

Peer-Reviewed Papers
15

References

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