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688487

Sigma-Aldrich

2-Mesityl-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazol-4-ium chloride

97%

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Synonym(s):
Bode Catalyst 3
Empirical Formula (Hill Notation):
C14H18ClN3
CAS Number:
Molecular Weight:
263.77
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

reaction suitability

reagent type: catalyst

mp

200-205 °C

SMILES string

[Cl-].Cc1cc(C)c(c(C)c1)-[n+]2cn3CCCc3n2

InChI

1S/C14H18N3.ClH/c1-10-7-11(2)14(12(3)8-10)17-9-16-6-4-5-13(16)15-17;/h7-9H,4-6H2,1-3H3;1H/q+1;/p-1

InChI key

KKBONGWVMVUYPA-UHFFFAOYSA-M

Application

Catalyst for:
  • Intermolecular hydroacylation of cyclopropenes
  • Crossed acyloin condensations
  • Domino ring-opening redox amidation Knoevenagel condensation
  • Claisen rearrangement
  • Lewis acid- and N-heterocyclic carbene-catalyzed cyclocondensation reaction
  • Bode catalyst for enantioselective cyclizations

Legal Information

Sold in collaboration with BioBlock, Inc.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Articles

Rovis has demonstrated that triazolium salt in the presence of a base can act as an N-heterocyclic carbene organocatalyst1 in highly enantioselective intramolecular Stetter reactions.

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

Related Content

The Bode Group aims to develop new reactions and reagents for the synthesis of complex molecules. The Bode Group has developed N-mesityl-substituted NHCs as organocatalysts for the catalytic generation of reactive species including activated carboxylates, homoenolates, and enolates. These novel catalysts and reactions have made possible a new generation of highly enantioselective annulations from simple starting materials under mild reaction conditions, usually at room temperature and without added reagents. Furthering the goal of designing new reagents to enable the assembly of complex molecules, the Bode group has developed SnAP reagents for the facile, one-pot conversion of aldehydes into N-unprotected, saturated N-heterocycles, including bicyclic and spirocyclic structures. These easy to handle reagents provide a simple and robust alternative to the challenging and restrictive cross-coupling methods for the functionalization of saturated N-heterocycles.

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