2,2,2-Trichloro-1-phenylethanol
[CAS# 2000-43-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic alcohol
• Name: 2,2,2-Trichloro-1-phenylethanol
• Molecular Formula: C₈H₇Cl₃O
• Molecular Weight: 225.50
• CAS Registry Number: 2000-43-3
• EC Number: 217-887-7
• SMILES: C1=CC=C(C=C1)C(C(Cl)(Cl)Cl)O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.585, Calc.^*, 1.569 (Expl.)
• Boiling Point: 289.4±35.0 °C (760 mmHg), Calc.^*, 325.6-330.3 °C (Expl.)
• Flash Point: 128.8±25.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2,2,2-Trichloro-1-phenylethanol is an organic compound that belongs to the class of alcohols. It consists of a phenylethanol structure with three chlorine atoms attached to the second carbon in the ethyl group. The molecular formula of 2,2,2-trichloro-1-phenylethanol is C8H7Cl3O, and it is known for its distinctive chemical structure, which includes both a hydroxyl group (-OH) and three chlorine atoms attached to the same carbon atom.

The discovery of 2,2,2-trichloro-1-phenylethanol occurred as part of the broader field of research into substituted phenylethanol derivatives. Phenylethanol compounds, due to their structural characteristics, have been studied extensively for their potential applications in the synthesis of various chemicals, particularly in the areas of pharmaceuticals, agrochemicals, and fragrance chemistry.

The synthesis of 2,2,2-trichloro-1-phenylethanol typically involves the chlorination of phenylethanol under controlled conditions. In the presence of chlorine, phenylethanol undergoes a substitution reaction where three chlorine atoms replace the hydrogen atoms on the second carbon of the ethyl group, leading to the formation of 2,2,2-trichloro-1-phenylethanol. This reaction may be carried out using a variety of chlorinating agents such as chlorine gas or chlorine-based compounds in a solvent under suitable temperature conditions.

2,2,2-Trichloro-1-phenylethanol has been explored for its potential applications in various fields of chemistry, particularly in industrial and synthetic processes. One of its notable uses is in the production of pesticides and herbicides, where its chlorine content and phenyl group contribute to its biological activity. Compounds with similar structures are often researched for their ability to control pest populations or influence plant growth, and derivatives of 2,2,2-trichloro-1-phenylethanol may be involved in the development of such products.

Additionally, 2,2,2-trichloro-1-phenylethanol has applications in the fragrance industry. The presence of the phenylethanol backbone, which is associated with floral and rose-like odors, combined with the unique chemical properties introduced by the trichloromethyl group, makes it useful as a fragrance compound in various consumer products.

The compound's reactivity and chemical characteristics are also of interest in organic synthesis. The trichloro group, being an electron-withdrawing group, can significantly influence the reactivity of the compound in further chemical transformations, making it a useful intermediate in the synthesis of more complex molecules. In particular, it may be used to introduce chlorinated functional groups into other organic molecules, thus broadening the range of potential chemical products that can be derived from this compound.

In terms of safety and handling, like many chlorinated compounds, 2,2,2-trichloro-1-phenylethanol requires careful handling due to its potential toxicity and environmental impact. As such, it is typically used in controlled industrial or laboratory settings where appropriate precautions are taken.

Overall, 2,2,2-trichloro-1-phenylethanol is a well-established chemical substance with applications primarily in the fields of pesticide and herbicide production, fragrance formulation, and synthetic organic chemistry. Its distinctive structure and properties make it a valuable compound for specific industrial applications, particularly where chlorinated phenylethanol derivatives are required.

References

1977. Reactions of Dichlorocarbene With Non-Olefinic Substrates. Reactivity and Structure: Concepts in Organic Chemistry, 5.
DOI: 10.1007/978-3-642-46357-0_3

2001. Homogeneous Electrocatalysis of the Trichloromethylphenylcarbinol Production by the Electroreduction of Chloroform and Benzaldehyde Mixed in Dimethylformamide. Russian Journal of Electrochemistry, 37(5).
DOI: 10.1023/a:1016640507756

2019. Addition Reaction of Benzaldehydes and Chloroform Catalyzed by Modified Calcium Oxide. Russian Journal of Physical Chemistry A, 93(10).
DOI: 10.1134/s003602441910008x