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(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

ALDRICH/683973 - 93%

Synonym: Bode Catalyst 2

CAS Number: 903571-02-8 (anhydrous)
Empirical Formula (Hill Notation): C21H22ClN3O · H2O
Molecular Weight: 385.89
MDL Number: MFCD20265585
Linear Formula: C21H22ClN3O · H2O
Product Type: Chemical

Catalog Number PKG Qty. Price Quantity
45-683973-100MG 100 mg
$233.00
1/EA
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45-683973-250MG 250 mg
$553.00
1/EA
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assay 93%
form solid
functional group ether
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
mp 226-230 °C
optical activity [α]20/D +158°, c = 1 in chloroform
Quality Level 100 
SMILES string [Cl-].Cc1cc(C)c(c(C)c1)-[n+]2c[n@@H]3[C@@H]4[C@@H](Cc5ccccc45)OCc3n2
Application: (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 can be used as a catalyst:
• In the preparation of dihydropyridinones by reacting enals or α′-hydroxyenones with vinylogous amides via aza-Claisen annulations.
• In the oxidative coupling reactions of di(hetero)arylmethanes with enals to yield benzimidazole fused lactams.
• In the synthesis of organosilanes by reacting enals with β-silyl enones.

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.
Legal Information: Sold in collaboration with BioBlocks, Inc.
Packaging: 100 mg in clear glass bottle
Packaging: 250 mg in amber glass bottle
Purity 93%
mp 226-230 °C
UNSPSC 12352005

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