2-CHLORO-1-(3-HYDROXYPHENYL) ETHAN-1- ONE

Product Description

2Chloro13hydroxyphenylethan1one is an organic compound featuring a chlorosubstituted ethanone group with a hydroxylated aromatic ring Heres a detailed overview of the compound

Chemical Information

Chemical Name 2Chloro13hydroxyphenylethan1one

Chemical Formula C8H9ClO2

Molecular Weight 17061 gmol

Structure

The compound consists of a chloro group Cl at the 2position of an ethanone acetyl group

The 13hydroxyphenyl part indicates a phenyl ring benzene with a hydroxyl group OH at the 3position ie a hydroxyl group on the meta position of the phenyl ring

The structure can be described as a chloroketone with a hydroxyphenyl substitution

Physical Properties

Appearance Usually a pale yellow or offwhite solid

Melting Point 8590C subject to purity and specific conditions

Boiling Point Not readily available but expected to be around 250270C

Solubility

Slightly soluble in water due to the hydroxyl group but more soluble in organic solvents like ethanol methanol acetone and dichloromethane

Applications

1 Intermediate in Organic Synthesis

The compound is commonly used as an intermediate in the synthesis of various pharmaceuticals agrochemicals and fine chemicals

Its functional groups chloro and hydroxy make it versatile for further chemical modifications like nucleophilic substitutions reduction reactions and coupling reactions

2 Pharmaceutical Chemistry

Potential precursor for synthesizing biologically active compounds particularly those that require a hydroxyphenyl group which is a motif in many drugs

The chloro group enhances electrophilic reactivity and makes it reactive in further derivatizations

3 Research Applications

Used in chemical research for investigating reactions involving chloro ketones and phenolic derivatives

May also be studied for potential antimicrobial antiinflammatory or other therapeutic properties

Reactivity

Chloro Group Cl

The chloro substituent makes the carbonyl carbon more electrophilic allowing for nucleophilic substitution reactions eg replacement by amines alcohols or thiols

It can also participate in halogenation reactions adding to its synthetic versatility

Hydroxy Group OH

The hydroxyl group at the 3position on the phenyl ring is an electrondonating group which increases the nucleophilicity of the aromatic ring and may facilitate electrophilic aromatic substitution eg nitration sulfonation

It can also undergo esterification or etherification under appropriate conditions

Ketone Group CO

The carbonyl group is reactive in various condensation reactions and can undergo nucleophilic attack or reduction to form alcohols

Safety and Handling

Hazards

The compound should be handled with care as the chloro group can be irritating to the skin eyes and respiratory tract

It may also be harmful if ingested or inhaled

Handling

Wear gloves goggles and a lab coat Handle in a wellventilated area preferably under a fume hood

Storage

Store in a cool dry place away from light and moisture Ensure that the container is tightly sealed to prevent contamination

Synthesis

General Synthesis Route

This compound can be synthesized by reacting 3hydroxyacetophenone or 3hydroxyphenylethanone with a chlorinating agent such as thionyl chloride SOCl or phosphorus trichloride PCl

Another approach could involve the FriedelCrafts acylation reaction where a chloroacetyl group is introduced to the hydroxylsubstituted aromatic ring

Would you like more details on its synthetic routes or would you prefer to explore its reactivity in more depth