• (+)-(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 (CAS 903571-02-8) - TCI D3983 - AMI Scientific
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TCI

CAS 903571-02-8

(+)-(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 TCI D3983

(+)-(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 TCI D3983
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Rp 5.076.750,00
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TCI D3983 (+)-(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 is a chiral triazolium salt that serves as an N-heterocyclic carbene organocatalyst precursor. The compound belongs to the organocatalyst category within the field of catalysis, and it is used in asymmetric synthesis laboratories to deliver products with high enantiomeric purity. When treated with a suitable base, this triazolium salt loses a proton at the key position and forms the active carbene species, which is able to invert the polarity of a carbonyl group and direct the formation of new bonds to a single face of the molecule.

The feature that makes this catalyst a preferred choice is its rigid fused indanol framework combined with a mesityl group — 2,4,6-trimethylphenyl — on the triazolium nitrogen atom. The rigidity of the bicyclic structure produces a clearly defined chiral environment around the catalytic centre, while the bulky mesityl group provides directed steric hindrance so that a substrate can only approach from one particular orientation. The firmly assigned (5aR,10bS) configuration ensures that the catalyst consistently generates the intended product enantiomer, which is what allows results to be reproduced from one batch to the next.

In Indonesian laboratories, this material is typically used in university and institutional research groups working on asymmetric methodology, in synthetic organic chemistry programmes, and in laboratories developing routes toward chiral building blocks. It is generally handled on a small scale in glassware under controlled conditions, where a defined chiral catalyst is required rather than a resolution step, and where the enantiomeric outcome of each reaction has to be verified analytically.

  • Asymmetric organocatalysis — the defined (5aR,10bS) configuration and rigid framework give a single reliable chiral environment, so reactions favour one product enantiomer.
  • N-heterocyclic carbene generation — deprotonation of the triazolium salt with a suitable base releases the active carbene species needed as the working catalyst in situ.
  • Umpolung (polarity reversal) chemistry — the carbene formed from this salt inverts the normal polarity of carbonyl groups, opening bond constructions unavailable under classical conditions.
  • Enantioselective bond-forming reactions — the bulky mesityl substituent blocks one approach path, restricting substrate orientation and directing new bonds to a single molecular face.
  • Method development and catalyst screening — as a well-defined single-enantiomer precursor it serves as a reference organocatalyst when comparing conditions, bases, and substrate scope.

Brand TCI
CAS number 903571-02-8
Molecular formula —
Purity —
Category Chemistry > Catalysis and Inorganic Chemistry > Organocatalysts [Catalysis]
Pack sizes supplied in standard TCI research-scale catalogue packs; please confirm the available size when ordering
Physical form crystalline triazolium chloride salt, isolated as the monohydrate
Storage keep tightly closed in a cool, dry place, protected from moisture

Store the container tightly closed in a cool, dry, well-ventilated place away from moisture, since the material is a hygroscopic-type salt isolated as a monohydrate and its handling properties depend on controlled water content. Original tightly sealed glass or amber bottles are suitable; keep the closure intact and consider a desiccator or secondary sealed container for opened bottles. Weigh and transfer in a fume hood using dry spatulas and dry glassware, wearing safety glasses, a laboratory coat, and chemically resistant gloves. Avoid dust formation, inhalation, and contact with skin and eyes. Keep away from strong bases and incompatible reagents in storage, label all working solutions clearly, and consult the manufacturer's safety data sheet before use and for disposal.

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