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TCI

CAS 132747-20-7

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane Dihydrobromide TCI D2658

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane Dihydrobromide TCI D2658
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Description

TCI D2658, (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane Dihydrobromide (CAS 132747-20-7), is a chiral bicyclic diamine supplied as its dihydrobromide salt. The bicyclo[2.2.1]heptane framework, carrying two nitrogen atoms at positions 2 and 5, produces a rigid bridged structure with a clearly defined (1S,4S) stereochemical configuration. In the laboratory it is regarded as a high-value chiral building block, because it provides a ready-to-use chiral nitrogen scaffold that is difficult to prepare in-house through conventional synthesis. Having it on the shelf saves considerable time on routes toward active molecules and asymmetric ligands.

The properties that make this compound a preferred choice are its conformational rigidity and its stereochemical purity. Because the bicyclic framework is almost incapable of free rotation, the two nitrogen atoms are held in fixed spatial orientations relative to one another. This produces a consistent chiral environment, which is extremely useful for controlling the direction from which a reagent approaches a substrate in asymmetric reactions. The dihydrobromide salt form adds practical advantages: it is a more stable solid, it does not readily absorb carbon dioxide, and it is easier to weigh accurately than the free diamine, which is strongly basic and hygroscopic.

In Indonesian laboratories, this material typically appears in synthetic and medicinal chemistry groups at universities and research institutes, and in R&D units developing fine chemicals or pharmaceutical intermediates. It is normally purchased in small quantities for method development and route scouting rather than for bulk production. Because the salt form tolerates ambient handling better than the free base, it suits laboratories where reagents are weighed on an open bench and where a genuinely inert-atmosphere workflow is not always practical.

Laboratory Applications

  • Chiral ligand synthesis — the fixed geometry of the two nitrogen donors makes it a direct precursor to bidentate nitrogen ligands with a predictable, reproducible chiral pocket around the metal centre.
  • Asymmetric catalysis studies — the rigid, stereochemically defined framework helps steer the approach of reagents to one face of a substrate, supporting systematic screening of enantioselective transformations.
  • Pharmaceutical intermediate routes — supplies a pre-formed chiral diazabicyclic core to medicinal chemistry programmes, removing several difficult stereoselective steps from the overall synthetic sequence.
  • Chiral building block library work — used as a stock scaffold for diversification at either nitrogen, letting chemists build analogue series while retaining the same defined (1S,4S) configuration throughout.
  • Method development and route scouting — the stable, easily weighed dihydrobromide salt is convenient for small-scale trial reactions where accurate charging of a chiral amine matters more than bulk quantity.

Specifications

  • Brand: TCI (Tokyo Chemical Industry)
  • Product code: D2658
  • CAS number: 132747-20-7
  • Chemical name: (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane Dihydrobromide
  • Category: Chemistry > Asymmetric Synthesis > Chiral Building Blocks
  • Physical form: solid (dihydrobromide salt); pack sizes available on request
  • Storage: keep in a tightly closed container, protected from moisture

Handling and Storage

Store the container tightly closed in a cool, dry place, away from moisture and from direct sunlight. Amine salts of this type are best kept in their original tightly sealed glass or chemically compatible plastic container, with the cap replaced immediately after each use to limit exposure to atmospheric humidity. Weigh the solid in a fume hood or well-ventilated area using clean, dry spatulas, and avoid creating dust. Wear safety glasses, gloves, and a laboratory coat, and avoid contact with skin, eyes, and clothing. Because the free amine liberated from this salt is strongly basic, handle any neutralisation step with care and add base slowly with cooling. Keep the material segregated from strong oxidising agents, label all secondary containers clearly, and consult the manufacturer's safety data sheet before first use.

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