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4-Chlorophenol
[CAS# 106-48-9]

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Identification
ClassificationOrganic raw materials >> Alcohols, phenols, phenolic compounds and derivatives >> Phenol and its halogenated, sulfonated, nitrated or nitrosated derivatives
Name4-Chlorophenol
Synonyms4-Hydroxychlorobenzene
Molecular StructureCAS # 106-48-9, 4-Chlorophenol
Molecular FormulaC6H5ClO
Molecular Weight128.56
CAS Registry Number106-48-9
EC Number203-402-6
SMILESC1=CC(=CC=C1O)Cl
Properties
Density1.306
Melting point41-45 °C
Boiling point220 °C
Flash point121 °C
Water solubility2.7 g/100 mL (20 °C)
Safety Data
Hazard Symbolssymbol symbol symbol symbol   GHS05;GHS06;GHS07;GHS09 Danger  Details
Risk StatementsH290-H301-H302-H312-H314-H318-H332-H411  Details
Safety StatementsP234-P260-P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P362+P364-P363-P390-P391-P405-P406-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Chronic hazardous to the aquatic environmentAquatic Chronic2H411
Acute toxicityAcute Tox.4H332
Acute toxicityAcute Tox.4H312
Serious eye damageEye Dam.1H318
Acute toxicityAcute Tox.3H301
Skin corrosionSkin Corr.1BH314
Acute toxicityAcute Tox.4H302
Substances or mixtures corrosive to metalsMet. Corr.1H290
Acute toxicityAcute Tox.3H311
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2H319
Acute toxicityAcute Tox.1H330
Skin corrosionSkin Corr.1CH314
Acute toxicityAcute Tox.4H301
Transport InformationUN 2904; UN 2905; UN 2020
SDSAvailable
up Discovery and Applications
4-Chlorophenol is an organic compound characterized by a phenolic structure with a chlorine atom substituted at the para position. Its molecular formula is C6H5ClO, and it is a white to pale yellow crystalline solid with a distinct medicinal odor. The compound has significant importance in both industrial applications and chemical research, making it a notable substance in organic chemistry.

The discovery of 4-chlorophenol dates back to the late 19th century, when chemists were investigating the properties of chlorinated phenols. These compounds were synthesized through the chlorination of phenol, a process that involves the reaction of phenol with chlorine gas in the presence of a catalyst. The production of 4-chlorophenol specifically can be attributed to the preference of chlorine to substitute hydrogen atoms at the para position due to steric and electronic factors. This method of synthesis has since been refined and optimized for industrial production.

One of the primary applications of 4-chlorophenol is in the synthesis of various chemical intermediates and pharmaceutical compounds. It serves as a crucial starting material for the production of agrochemicals, such as herbicides and fungicides. For instance, 4-chlorophenol can be used to synthesize compounds like chlorophenoxy herbicides, which are widely employed in agricultural practices to control weeds. Its effectiveness in disrupting the growth of unwanted plants has made it an essential component in modern crop management.

Additionally, 4-chlorophenol is utilized in the production of antiseptic agents and disinfectants. Due to its antimicrobial properties, it is included in formulations aimed at sterilizing surfaces and sanitizing medical equipment. The compound’s ability to inhibit bacterial growth has made it a valuable ingredient in various hygiene products, including hand sanitizers and household cleaners. Its effectiveness against a broad spectrum of microorganisms enhances its application in maintaining health and safety standards.

Moreover, 4-chlorophenol is an important reagent in the field of organic synthesis. It is commonly used in the preparation of phenolic resins, which are utilized in adhesives, coatings, and plastics. The incorporation of 4-chlorophenol into resin formulations contributes to improved thermal stability and mechanical strength, making it suitable for use in a variety of industrial applications. Its role in enhancing the properties of polymeric materials demonstrates the versatility of this compound in material science.

Despite its beneficial applications, the use of 4-chlorophenol is associated with environmental and health concerns. It is classified as a hazardous substance, and exposure can lead to adverse health effects, including skin irritation and respiratory issues. As a result, regulatory measures have been implemented to control its use and limit emissions in industrial processes. Manufacturers are encouraged to adopt best practices and safety protocols to mitigate the risks associated with handling this compound.

In conclusion, 4-chlorophenol is a significant organic compound with diverse applications in agriculture, pharmaceuticals, and materials science. Its role as a chemical intermediate and its effectiveness as an antimicrobial agent underline its importance in various industries. As research continues to explore safer and more efficient methods for its use, 4-chlorophenol is likely to remain a relevant substance in the field of organic chemistry and industrial applications.

References

2024. Novel Pd-Fe2O3-Ni Electrocatalyst with Low Pd Content for Electrochemical Reduction of 4-Chlorophenol. Catalysis Letters, 154, 1-12.
DOI: 10.1007/s10562-024-04850-4

2010. Preparation and properties of visible light responsive ZrTiO4/Bi2O3 photocatalysts for 4-chlorophenol decomposition. Journal of Hazardous Materials, 183(1-3), 701-707.
DOI: 10.1016/j.jhazmat.2010.06.069

2009. Effect of inorganic, synthetic and naturally occurring chelating agents on Fe(II) mediated advanced oxidation of chlorophenols. Water Research, 43(3), 678-686.
DOI: 10.1016/j.watres.2008.10.045
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