4-(2,2-Dichlorocyclopropyl)phenol acetate
[CAS# 144900-34-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 4-(2,2-Dichlorocyclopropyl)phenol acetate
• Synonyms: 4-(2,2-Dichlorocyclopropyl)phenol 1-acetate
• Molecular Formula: C₁₁H₁₀Cl₂O₂
• Molecular Weight: 245.10
• CAS Registry Number: 144900-34-5
• EC Number: 924-945-1
• SMILES: CC(=O)OC1=CC=C(C=C1)C2CC2(Cl)Cl

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 340.8±42.0 ºC 760 mmHg (Calc.)^*
• Flash point: 143.2±26.9 ºC (Calc.)^*
• Index of refraction: 1.572 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS09 Warning
• Hazard Statements: H411
• Precautionary Statements: P273-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovory and Applicatios

4-(2,2-Dichlorocyclopropyl)phenol acetate is a synthetic organic compound characterized by a phenol acetate moiety substituted at the 4-position with a 2,2-dichlorocyclopropyl group. The molecular structure integrates a phenyl ring bearing an acetate ester linked to the phenolic oxygen and a cyclopropane ring substituted with two chlorine atoms at the 2-position. This combination of functional groups imparts distinct chemical properties relevant in both synthetic chemistry and applied fields such as agrochemicals and pharmaceuticals.

The phenol acetate portion of the molecule is derived from acetylation of a phenol group, resulting in an ester linkage (–O–COCH₃). This modification enhances the compound's stability and lipophilicity relative to the free phenol. Esterification of phenols is a common strategy to modulate solubility, reactivity, and bioavailability of molecules. The acetate ester can be hydrolyzed enzymatically or chemically under basic or acidic conditions to regenerate the phenolic hydroxyl group.

The 2,2-dichlorocyclopropyl substituent attached at the para position (4-position) of the phenyl ring is a small, strained three-membered ring bearing two chlorine atoms at the same carbon. Cyclopropane rings are known for their ring strain and unique reactivity, often serving as versatile synthetic intermediates. The dichloro substitution increases the electrophilicity of the cyclopropane carbon and can affect the compound's chemical stability and interactions with biological targets. Such halogenated cyclopropane motifs are frequently employed in agrochemical agents for their potency and resistance to metabolic degradation.

Synthesis of 4-(2,2-dichlorocyclopropyl)phenol acetate typically involves initial preparation of 4-(2,2-dichlorocyclopropyl)phenol, which can be obtained via cyclopropanation reactions using dichlorocarbene intermediates and para-substituted phenols or their derivatives. Subsequent acetylation of the phenolic hydroxyl group is achieved by reaction with acetic anhydride or acetyl chloride in the presence of a base or acid catalyst to form the acetate ester.

The chemical properties of this compound allow it to act as a precursor for further transformations. The strained cyclopropane ring can be opened or functionalized under specific conditions, providing routes to diverse cyclopropyl-containing derivatives. Additionally, the acetate group serves as a protective group or as a functional handle for targeted hydrolysis or conjugation reactions.

In applied research, compounds featuring halogenated cyclopropyl groups linked to aromatic systems have been studied for biological activity, especially in the development of herbicides, insecticides, and fungicides. The structural motif enhances target specificity and environmental stability, contributing to the efficacy of agrochemical products. While the exact bioactivity of 4-(2,2-dichlorocyclopropyl)phenol acetate depends on further functionalization and testing, related compounds have demonstrated potent activity against various pests and pathogens.

Analytical characterization of this compound is performed using techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry. In ²H NMR, signals correspond to aromatic protons of the phenyl ring, methylene or methine protons of the cyclopropane ring, and the methyl group of the acetate ester. Carbon-13 NMR confirms the presence of carbonyl carbon, aromatic carbons, and cyclopropane carbons. IR spectroscopy displays characteristic ester carbonyl stretching near 1740 cm⁻¹ and C–Cl stretching vibrations. Mass spectrometry provides molecular ion peaks and isotopic patterns consistent with dichlorinated compounds.

Physically, the compound is expected to be a crystalline solid or viscous liquid with moderate solubility in organic solvents such as chloroform, dichloromethane, and ethyl acetate, while its solubility in water is limited due to the hydrophobic cyclopropyl and aromatic groups.

In conclusion, 4-(2,2-dichlorocyclopropyl)phenol acetate is a chemically and structurally distinct compound combining a halogenated cyclopropane ring with an acetylated phenol. Its synthesis, functional properties, and potential applications in agrochemical development and organic synthesis underscore its relevance as an intermediate and functional molecule in chemical research.

References

2024. List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2. Zenodo.
DOI: 10.5281/zenodo.10944198