(1R,2R,5R)-(+)-2-Hydroxy-3-pinanone TCI H0862

Chemical Identity

CAS No.: 24047-72-1
PubChem: CID 6553882·SID 87571219
Formula: C10H16O2
Molecular weight: 168.23 g/mol
Purity: >98.0%(GC)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: (1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
SMILES: C[C@]1([C@@H]2C[C@@H](C2(C)C)CC1=O)O
InChIKey: VZRRCQOUNSHSGB-BRDIYROLSA-N

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TCI H0862 (1R,2R,5R)-(+)-2-Hydroxy-3-pinanone is a chiral bicyclic ketone built on the pinane skeleton, a rigid bridged structure derived from the terpene family. The compound belongs to the chiral building block class and is widely recognised as a chiral auxiliary in asymmetric synthesis. The presence of a ketone group and a tertiary hydroxyl on the rigid framework creates a highly defined spatial environment, allowing the molecule to direct the formation of new stereogenic centres in substrates reacted alongside it across a range of organic transformations in research laboratories.

The principal properties that make it a preferred choice are the rigidity of the bicyclic framework and the configurational purity at its three stereogenic centres. The bridged pinane shape leaves one face of the molecule far more exposed than the other, so incoming reagents approach from the favoured direction and deliver products with meaningful enantiomeric excess. The ketone group can form Schiff bases with glycine esters and other amines, producing chiral synthons widely used in the synthesis of unusual amino acids. Once the reaction is complete, the auxiliary can be released by hydrolysis.

In Indonesian laboratories this material is typically used in university and institutional research settings working on asymmetric synthesis and chiral methodology development. It suits organic chemistry research groups preparing non-proteinogenic amino acids, method development work where stereochemical control must be demonstrated, and postgraduate projects investigating chiral auxiliary strategies. Because it functions as a building block rather than a bulk reagent, it is normally handled in small research quantities on the bench.

TCI brochures (PDF)

Asymmetric Synthesis 2026-03-18 · p. 6
Terpenes 2025-09-22 · p. 6

Related TCI products

Asymmetric amino acid synthesis — the ketone condenses with glycine esters to form Schiff base synthons that direct alkylation toward one face, giving access to non-proteinogenic amino acids.
Chiral auxiliary methodology — the rigid pinane framework provides a well-defined steric environment that biases reagent approach, then releases cleanly by hydrolysis once the new stereocentre is set.
Stereoselective alkylation studies — the pronounced facial difference between the two sides of the bicyclic skeleton allows researchers to obtain products with meaningful enantiomeric excess under controlled conditions.
Chiral building block applications — the compound supplies a pre-formed terpene-derived scaffold with three defined stereogenic centres, shortening routes to more elaborate enantiomerically enriched target molecules.
Asymmetric synthesis method development — its established behaviour as an auxiliary makes it a useful benchmark substrate when comparing new stereochemical control strategies against known transformations in the laboratory.

Brand	TCI (Tokyo Chemical Industry)
CAS number	24047-72-1
Molecular formula	—
Purity	—
Category	Chemistry > Asymmetric Synthesis > Chiral Building Blocks
Pack sizes	available in standard TCI research pack sizes; please confirm the packaging option required when ordering
Physical form	—
Storage	keep in a cool, dry place in the tightly closed original container

Catalogue number: H0862

Store the product in its tightly closed original container in a cool, dry and well-ventilated place, away from direct sunlight, heat sources and incompatible chemicals such as strong oxidising agents. Keep the container closed when not in use to limit moisture uptake and exposure to air, and return the material to storage promptly after weighing. Handle in a fume hood using standard laboratory personal protective equipment, including safety glasses, a laboratory coat and suitable chemical-resistant gloves. Avoid contact with skin and eyes and avoid breathing any dust or vapour. Use clean, dry spatulas and glassware to prevent contamination of the remaining stock, and label all secondary containers clearly. Always consult the manufacturer's Safety Data Sheet before use and follow institutional procedures for chemical waste disposal.

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