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Description
TCI D3423 DL-1,4-Dichloro-2,3-butanediol is a synthetic chemical building block based on a four-carbon chain that carries two hydroxyl groups at the 2 and 3 positions and a chlorine atom at each end of the chain. The DL designation indicates that the material is supplied as a racemic mixture. Its role in the laboratory is to provide a highly versatile symmetrical bifunctional skeleton: the two chlorine atoms act as leaving groups for substitution reactions, while the hydroxyl pair in the middle of the chain can be protected, oxidised, or used for ring formation, so that a single starting material can lead to several different classes of product.
The characteristics that make this material a preferred choice are its symmetry pattern and the close spacing of its functional groups, which facilitates ring-closing reactions. Treatment with base allows the formation of epoxide rings or cyclic ethers, while the vicinal diol pair can be converted into acetals, cyclic ketals, or cyclic sulfates in order to tune subsequent reactivity. The two primary chlorine atoms are relatively easy to displace with oxygen, nitrogen, or sulfur nucleophiles, so the chain can be extended at both ends either simultaneously or in a stepwise fashion. The molecule additionally provides two stereogenic centres within a compact framework.
In Indonesian laboratories, a non-heterocyclic building block of this type is typically used in synthetic organic chemistry groups at universities and research institutes, as well as in the development laboratories of chemical and pharmaceutical companies. It is generally handled on a small preparative scale for route exploration, intermediate preparation, and the construction of ring systems or extended chains, where a well-defined bifunctional starting material shortens a synthetic sequence and keeps the number of separate reagents required to a minimum.
Laboratory Applications
- Epoxide and cyclic ether synthesis: base treatment closes a ring directly from the chloro-hydroxy arrangement, giving access to strained or cyclic ether intermediates without a separate activation step.
- Bis-nucleophilic substitution and chain extension: the two primary chlorine atoms are readily displaced by oxygen, nitrogen, or sulfur nucleophiles, allowing symmetrical or stepwise elongation at both chain ends.
- Diol protection chemistry: the vicinal hydroxyl pair converts cleanly into acetals or cyclic ketals, letting chemists mask the centre of the molecule while the terminal chlorides react selectively.
- Cyclic sulfate preparation: the adjacent hydroxyl groups can be transformed into a cyclic sulfate, a common tactic for raising electrophilicity and controlling the site of subsequent nucleophilic attack.
- Stereochemical route development: two stereogenic centres in a compact, symmetrical framework make the racemate useful for resolution studies and for probing diastereoselectivity in ring-forming reactions.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS Number: 2419-73-0
- Product Code: D3423
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research-scale packaging; please confirm the currently offered pack size when ordering
- Storage: keep in the tightly closed original container under the conditions stated on the manufacturer's label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area away from heat, ignition sources, moisture, and incompatible materials such as strong bases and strong oxidising agents, following the temperature guidance printed on the manufacturer's label. Keep the material in its original supplier container, or in a chemically compatible, clearly labelled and tightly sealed vessel if transferred. Handle in a fume hood using safety glasses, chemically resistant gloves, and a laboratory coat, since organochlorine compounds may irritate skin, eyes, and the respiratory tract. Avoid dust or vapour generation, close the container immediately after weighing to limit moisture uptake, and consult the safety data sheet before first use as well as for spill response and waste disposal.
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