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CAS 83-38-5

2,6-Dichlorobenzaldehyde TCI D0331

2,6-Dichlorobenzaldehyde TCI D0331

Chemical Identity

CAS No.
83-38-5
PubChem
CID 6737·SID 87567024
Formula
C7H4Cl2O
Molecular weight
175.01 g/mol
Purity
>97.0%(GC)
Reference databases
ChemSpider·ECHA
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
2,6-dichlorobenzaldehyde
SMILES
C1=CC(=C(C(=C1)Cl)C=O)Cl
InChIKey
DMIYKWPEFRFTPY-UHFFFAOYSA-N
MDL
MDL00003307
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2,6-Dichlorobenzaldehyde from TCI (CAS 83-38-5) is an aromatic aldehyde with two chlorine atoms on either side of the formyl group, at positions 2 and 6 of the benzene ring. It is a non-heterocyclic building block and serves as a starting material for carbon-carbon and carbon-nitrogen bonds through typical aldehyde reactions. These include condensations, nucleophilic additions, and the formation of imines, oximes, and hydrazones. The 2,6-dichlorophenyl group it introduces is common in bioactive molecules and agrochemicals.

The compound's most distinctive feature is the steric hindrance created by the two ortho chlorine atoms. This crowding affects the rate and selectivity of reactions at the aldehyde group, and it can make the conformation of the resulting products more rigid. Drug designers often use this effect to control molecular shape. The electron-withdrawing chlorine atoms also make the carbonyl carbon more electrophilic. Because the compound combines these steric and electronic effects, it is a useful substrate for synthetic methodology studies, where chemists need to see how reactivity and selectivity respond to crowded and electronically activated carbonyl centres.

In Indonesian laboratories, 2,6-Dichlorobenzaldehyde is used in medicinal chemistry research and in the synthesis of chalcone derivatives, Schiff bases, and heterocyclic compounds. University research groups, graduate students, and industrial R&D teams use it to prepare libraries of related compounds for structure-activity studies. Agrochemical development groups also use it when they need the 2,6-dichlorophenyl group. Because TCI is a recognised reagent brand, laboratories can rely on consistent material from one batch to the next for synthesis work and published research.

  • Medicinal chemistry research: the 2,6-dichlorophenyl group appears in many bioactive molecules, and its ortho chlorine atoms help researchers control the shape and rigidity of drug candidates.
  • Chalcone synthesis: the reactive aldehyde group undergoes condensation with ketones, so researchers can build chalcone derivatives that carry a sterically hindered, electron-poor aromatic ring.
  • Schiff base preparation: the electrophilic carbonyl carbon reacts readily with primary amines to form imines, which are used as ligands, intermediates, and screening compounds in synthetic laboratories.
  • Heterocycle construction: as a non-heterocyclic building block, the compound supplies the aldehyde carbon for ring-forming reactions that lead to many heterocyclic structures used in pharmaceutical and materials research.
  • Synthetic methodology studies: the combined steric hindrance and electronic activation make it a demanding test substrate for new condensation, addition, and C–N bond-forming methods.

Brand TCI (product code D0331)
CAS number 83-38-5
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes as listed on the product page for this item
Physical form see the TCI product label and certificate of analysis
Storage keep tightly closed in a cool, dry, well-ventilated place; follow the TCI Safety Data Sheet

Keep 2,6-Dichlorobenzaldehyde in its original, tightly sealed container in a cool, dry, well-ventilated area, away from heat, direct sunlight, and strong oxidising agents. Aldehydes can slowly oxidise in air, so reseal the container promptly after each use. If the product is used often, transfer smaller portions into clean, inert, airtight glass containers. Handle it in a fume hood and wear safety glasses, chemical-resistant gloves, and a lab coat. Avoid inhaling dust or vapour and avoid contact with skin and eyes. Always check the TCI Safety Data Sheet for hazard information, first aid measures, and disposal requirements before use.

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