2,6-Dichloro-1,4-benzoquinone TCI D0344

Chemical Identity

Other names: 2,6-Dichloro-p-quinone
CAS No.: 697-91-6
PubChem: CID 12771·SID 87567035
Formula: C6H2Cl2O2
Molecular weight: 176.98 g/mol
Purity: >98.0%(GC)(T)
Reference databases: ChEBI·ECHA·Wikipedia

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 2,6-dichlorocyclohexa-2,5-diene-1,4-dione
SMILES: C1=C(C(=O)C(=CC1=O)Cl)Cl
InChIKey: JCARTGJGWCGSSU-UHFFFAOYSA-N
MDL: MDL00037159

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2,6-Dichloro-1,4-benzoquinone from TCI is a derivative of p-benzoquinone that carries two chlorine atoms at the 2 and 6 positions of the quinone ring. Quinones are a class of compounds known as electron acceptors and oxidizing agents. In the laboratory, this compound serves as a building block in organic synthesis, as a dienophile in Diels-Alder reactions, and as a mild oxidant. It also draws interest in environmental studies, because halobenzoquinones are known to form as by-products when drinking water is disinfected with chlorine.

Researchers choose this compound because the chlorine atoms make the electron-poor quinone ring even more electrophilic. As a result, it reacts readily with nucleophiles such as amines and thiols, and it is a stronger electron acceptor. The 2,6 substitution pattern leaves the other two vinyl positions open for addition or substitution reactions, which gives chemists room to design new derivatives. Its redox behavior also makes it a useful subject for voltammetry and other electrochemical techniques, where researchers can study how chlorine substitution changes the electron-accepting character of the quinone core.

In Indonesia, this compound is relevant to synthetic organic chemistry laboratories that need a reactive quinone building block, to electrochemistry and redox materials research groups studying electron-transfer behavior, and to laboratories working on environmental chemistry and water quality, where halobenzoquinones are studied as disinfection by-products. University research groups, research institutes, and analytical laboratories can use it in synthesis, mechanistic studies, and method development.

Related TCI products

Organic synthesis building block: the electrophilic dichlorinated quinone ring and its two open vinyl positions allow chemists to build new substituted quinone derivatives in a controlled way.
Diels-Alder reactions: as an electron-poor dienophile, the compound reacts with dienes to form cyclic adducts, which makes it useful for building more complex ring systems in synthesis.
Mild oxidation reactions: as a quinone, it acts as an oxidizing agent and can be used in the laboratory where a mild oxidant is preferred over harsher reagents.
Reactions with amines and thiols: the chlorine atoms increase the electrophilicity of the ring, so the compound reacts readily with these nucleophiles for derivatization and reactivity studies.
Electrochemical and environmental studies: its redox properties suit voltammetry research, and its status as a known halobenzoquinone makes it relevant to studies of drinking water disinfection by-products.

Brand	TCI (product code D0344)
CAS number	697-91-6
Molecular formula	—
Purity	—
Category	Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes	see the pack size options shown on this product page
Physical form	refer to the TCI product specification and certificate of analysis
Storage	follow the storage conditions on the TCI label and Safety Data Sheet

Keep the compound in its original, tightly closed TCI container, and store it in a cool, dry, well-ventilated area away from light, heat sources, strong reducing agents, and incompatible materials. Because it is an oxidizer and reacts with nucleophiles such as amines and thiols, store it apart from these substances. Wear gloves, safety glasses, and a lab coat when handling it, and weigh or transfer it in a fume hood so you do not inhale dust or vapors. Read the Safety Data Sheet before use and dispose of waste according to institutional and local regulations.

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