• (-)-(5aS,10bR)-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 (CAS 919102-70-8) - TCI D3984 - AMI Scientific
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TCI

CAS 919102-70-8

(-)-(5aS,10bR)-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 TCI D3984

(-)-(5aS,10bR)-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 TCI D3984
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TCI D3984 (-)-(5aS,10bR)-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 is a chiral triazolium salt that represents the enantiomeric counterpart of the (+) variant. The compound functions as a precursor for N-heterocyclic carbene organocatalysts and is used in the laboratory to run asymmetric reactions that deliver product configurations opposite to those obtained with its paired enantiomer. Once activated with a suitable base, the salt generates a carbene species capable of reversing the normal reactivity pattern of carbonyl groups and controlling the direction of nucleophilic and electrophilic attack during the bond-forming step.

The characteristics that make this catalyst valuable are its rigid indanol-derived bicyclic framework combined with the mesityl group installed on the triazolium nitrogen atom. The rigid structure locks the geometry of the catalytic centre, so the surrounding chiral environment stays consistent from one catalytic cycle to the next, while the bulky mesityl group shields one face of substrate approach. The (5aS,10bR) configuration ensures that the products formed carry stereochemistry opposite to the outcome obtained from the enantiomeric catalyst, which makes the pair useful for accessing either antipode of a target molecule.

In Indonesian laboratories, this triazolium salt is typically handled in university and institutional research groups working on asymmetric synthesis and methodology development, as well as in industrial R&D settings preparing enantioenriched intermediates. It is normally weighed out in small catalytic quantities, activated in situ with base, and used alongside the (+) enantiomer when a study requires both product configurations for comparison, assignment of absolute stereochemistry, or verification of catalyst-controlled selectivity.

  • Asymmetric NHC catalysis — the salt is deprotonated in situ to form the active carbene, and its fixed chiral pocket transfers stereochemical information directly to the newly formed bonds.
  • Carbonyl umpolung chemistry — after activation the carbene reverses the conventional polarity of carbonyl groups, opening bond constructions that are not accessible through standard nucleophilic addition chemistry.
  • Enantiodivergent synthesis — used deliberately in place of the (+) enantiomer when a laboratory needs the mirror-image product configuration from an otherwise identical reaction protocol and setup.
  • Stereochemical assignment studies — running a transformation with both enantiomers of this catalyst produces opposite antipodes, giving researchers a reliable internal reference for confirming absolute configuration.
  • Methodology and catalyst screening — the rigid indanol-derived scaffold with its mesityl substituent serves as a well-defined benchmark structure when comparing chiral triazolium precursors in reaction development.

Brand TCI
CAS number 919102-70-8
Molecular formula —
Purity —
Category Chemistry > Catalysis and Inorganic Chemistry > Organocatalysts [Catalysis]
Pack sizes available in laboratory research quantities as listed by the manufacturer; storage note — keep in a tightly closed original container, protected from moisture
Physical form —
Storage —
  • Chemical class: chiral triazolium salt, N-heterocyclic carbene (NHC) organocatalyst precursor
  • Hydration state: chloride monohydrate

Store the material in its original tightly closed container in a cool, dry, well-ventilated area, away from moisture, strong bases, and incompatible chemicals, since triazolium salts are hygroscopic and can be deactivated by uncontrolled exposure to atmospheric water. Weigh and transfer the solid using clean, dry spatulas and glassware, and reseal the container promptly after use. Handle in a fume hood with a laboratory coat, nitrile gloves, and safety glasses, and consult the manufacturer's safety data sheet before use, disposal, or transport. Keep containers clearly labelled and segregated from bulk reagents.

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