2',4'-Dichloroacetophenone
[CAS# 2234-16-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 2',4'-Dichloroacetophenone
• Synonyms: 1-(2,4-Dichlorophenyl)ethanone
• Molecular Formula: C₈H₆Cl₂O
• Molecular Weight: 189.04
• CAS Registry Number: 2234-16-4
• EC Number: 218-780-8
• SMILES: CC(=O)C1=C(C=C(C=C1)Cl)Cl

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*, 1.32 g/mL (Expl.)
• Melting point: 33-34 °C (Expl.)
• Index of Refraction: 1.549, Calc.^*, 1.563 (Expl.)
• Boiling Point: 246.7±20.0 °C (760 mmHg), Calc.^*, 291.1-304.4°C (Expl.)
• Flash Point: 100.9±22.3 °C, Calc.^*, 113 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H318-H412
• Safety Statements: P264-P264+P265-P270-P273-P280-P301+P317-P305+P354+P338-P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Germ cell mutagenicity	Muta.	2	H341
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2',4'-Dichloroacetophenone is a chemical compound belonging to the family of substituted acetophenones, characterized by the presence of two chlorine atoms attached to the aromatic ring at the 2' and 4' positions. It is a halogenated aromatic ketone, which has been studied for its chemical properties and applications in various fields.

The compound is synthesized through the introduction of chlorine atoms into acetophenone, a reaction typically carried out using chlorinating agents under controlled conditions. The substitution of chlorine atoms in the aromatic ring of acetophenone can influence the physical and chemical properties of the resulting compound, such as its reactivity, solubility, and stability.

2',4'-Dichloroacetophenone has been primarily investigated for its use in the synthesis of other chemical compounds. As a halogenated acetophenone derivative, it serves as an intermediate in the preparation of various pharmaceutical and chemical products. It is used in the manufacturing of certain types of agrochemicals and pharmaceuticals, where the halogen substitution enhances its chemical reactivity and functional group characteristics. The presence of chlorine atoms in the aromatic ring can improve the compound's ability to participate in further chemical reactions, such as nucleophilic substitution or addition reactions.

The compound's utility extends to the production of certain dyes, where its chlorinated structure is leveraged to alter the properties of the dye molecules. Additionally, it has been studied for its potential in the creation of materials with specific electronic or optical properties, as halogenated aromatic compounds often exhibit unique behaviors in these areas.

In industrial applications, 2',4'-dichloroacetophenone is also examined for its role in various chemical reactions involving the chlorination of organic compounds. Its reactivity makes it useful in the synthesis of other chemicals where halogen substitution is required. However, it is important to note that the compound's specific applications may vary depending on the specific needs of the chemical processes involved.

In summary, 2',4'-dichloroacetophenone is a halogenated acetophenone derivative with applications primarily in chemical synthesis. It serves as an intermediate in the preparation of various industrial chemicals, pharmaceuticals, and agrochemicals, as well as in the production of certain dyes and materials. The presence of chlorine atoms on the aromatic ring makes it a valuable compound for further chemical reactions, enhancing its reactivity and utility in various manufacturing processes.

References

1982. Glutathione-dependent reductive dehalogenation of 2,2′,4′-trichloroacetophenone to 2′,4′-dichloroacetophenone. Biochemical Pharmacology, 31(23).
DOI: 10.1016/0006-2952(82)90306-9

2009. Transition-Metal-Catalyzed Site-Selective Cross-Coupling of Di- and Polyhalogenated Compounds. Synthesis, 2009(09).
DOI: 10.1055/s-0029-1216632

2023. Site-selective cross-coupling of dihalogenated acetophenones and dihalogenated benzophenones with aryl titanium reagents under catalyst control. Monatshefte für Chemie - Chemical Monthly, 154(10).
DOI: 10.1007/s00706-023-03101-3