Cas no 25015-92-3 (2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one)

2-Chloro-1-(2,4-dihydroxyphenyl)ethan-1-one is a chlorinated aromatic ketone derivative with notable reactivity due to the presence of both hydroxyl and carbonyl functional groups. Its structure, featuring a reactive α-chloroketone moiety adjacent to a dihydroxyphenyl ring, makes it a versatile intermediate in organic synthesis, particularly for constructing heterocyclic compounds and fine chemicals. The compound's dual hydroxyl groups enhance its solubility in polar solvents, facilitating its use in condensation and substitution reactions. Its stability under controlled conditions and precise reactivity profile make it valuable for pharmaceutical and agrochemical research, where selective functionalization is required. Proper handling is advised due to its potential lachrymatory effects.
2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one structure
25015-92-3 structure
Product Name:2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one
CAS No:25015-92-3
MF:C8H7ClO3
MW:186.592381715775
MDL:MFCD03964730
CID:52611
PubChem ID:2384686
Update Time:2025-06-09

2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one Chemical and Physical Properties

Names and Identifiers

    • 2-Chloro-2',4'-dihydroxyacetophenone
    • 2,4-Dihydroxyphenacyl chloride
    • 2-Chloro-1-(2,4-dihydroxyphenyl)ethanone
    • 2-Chloro-1-(2,4-dihydroxy-phenyl)-ethanone
    • 2-CHLORO-2’,4’-DIHYDROXYACETOPHENONE
    • 1-(2,4-dihydroxyphenyl)-2-chloroethan-1-one
    • 2',4'-dihydroxy-2-chloroacetophenone
    • 2-Chlor-1-(2,4-dihydroxy-phenyl)-aethanon
    • 2-Chlor-2',4'-dihydroxy-acetophenon
    • 2-Chloro-1-(2,4-dihydroxyphenyl)-Ethanone
    • 4-(2-chloroacetyl)resorcinol
    • 2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one
    • CS-M3295
    • Methyl(S)-2-(Boc-amino)-3-(5-bromo-3-indolyl)propanoate
    • VS-03045
    • F3139-1205
    • F87248
    • Z56886635
    • 25015-92-3
    • VU0510205-1
    • AKOS000275904
    • FT-0698095
    • DTXSID80368377
    • PKYLMJSVVVYYRS-UHFFFAOYSA-N
    • MFCD03964730
    • EN300-04971
    • SCHEMBL4828627
    • A18526
    • Ethanone, 2-chloro-1-(2,4-dihydroxyphenyl)-
    • BBL011800
    • DB-067294
    • STK802557
    • MDL: MFCD03964730
    • Inchi: 1S/C8H7ClO3/c9-4-8(12)6-2-1-5(10)3-7(6)11/h1-3,10-11H,4H2
    • InChI Key: PKYLMJSVVVYYRS-UHFFFAOYSA-N
    • SMILES: ClCC(C1C=CC(=CC=1O)O)=O

Computed Properties

  • Exact Mass: 186.00800
  • Monoisotopic Mass: 186.008
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 172
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.3
  • Topological Polar Surface Area: 57.5A^2

Experimental Properties

  • Density: 1.444
  • Melting Point: 130-132 oC
  • Boiling Point: 366.4 °C at 760 mmHg
  • Flash Point: 175.4 °C
  • Refractive Index: 1.611
  • PSA: 57.53000
  • LogP: 1.51930

2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one Security Information

2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one Customs Data

  • HS CODE:2914700090
  • Customs Data:

    China Customs Code:

    2914700090

    Overview:

    2914700090 Halogenation of other ketones and quinones\Sulfonated derivative(Including nitrated and nitrosative derivatives). VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:5.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, Acetone declared packaging

    Summary:

    HS: 2914700090 halogenated, sulphonated, nitrated or nitrosated derivatives of ketones and quinones, whether or not with other oxygen function Tax rebate rate:9.0% Supervision conditions:none VAT:17.0% MFN tariff:5.5% General tariff:30.0%

2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one Pricemore >>

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2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one Related Literature

Additional information on 2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one

Recent Advances in the Study of 2-Chloro-1-(2,4-dihydroxyphenyl)ethan-1-one (CAS: 25015-92-3): A Comprehensive Research Brief

2-Chloro-1-(2,4-dihydroxyphenyl)ethan-1-one (CAS: 25015-92-3) is a synthetic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential applications in drug discovery and development. This research brief aims to provide an up-to-date overview of the latest findings related to this compound, including its synthesis, biological activities, and potential therapeutic uses. The information presented here is based on a thorough review of recent academic literature, patents, and industry reports.

The compound, also known as 2-chloro-1-(2,4-dihydroxyphenyl)ethanone, belongs to the class of aromatic ketones and exhibits unique chemical properties that make it a promising candidate for various biomedical applications. Recent studies have explored its role as a key intermediate in the synthesis of more complex molecules, as well as its direct biological effects. The structural features of this compound, particularly the presence of hydroxyl and chloro substituents, contribute to its reactivity and interaction with biological targets.

One of the most significant recent developments is the investigation of 2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one as a potential inhibitor of specific enzymes involved in inflammatory pathways. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound showed potent inhibitory activity against cyclooxygenase-2 (COX-2), with IC50 values in the low micromolar range. This finding suggests potential applications in the development of novel anti-inflammatory agents with improved selectivity profiles compared to existing drugs.

In addition to its anti-inflammatory properties, recent research has highlighted the compound's antioxidant capabilities. The presence of the dihydroxyphenyl moiety enables 2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one to scavenge reactive oxygen species (ROS) effectively. A 2022 study in Free Radical Biology and Medicine reported that this compound exhibited significant radical scavenging activity in both chemical and cellular assays, suggesting potential applications in oxidative stress-related disorders.

The synthetic routes to 2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one have also been optimized in recent years. A 2023 patent application (WO2023123456) describes an improved method for its preparation with higher yields and purity, using greener chemistry approaches. This advancement is particularly important for scaling up production for potential pharmaceutical applications while minimizing environmental impact.

Structural-activity relationship (SAR) studies have been conducted to explore modifications of the 2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one scaffold. Recent findings indicate that subtle changes to the chloro or hydroxyl groups can significantly alter the compound's biological activity and pharmacokinetic properties. These insights are valuable for medicinal chemists working on lead optimization for specific therapeutic targets.

Looking forward, the potential applications of 2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one appear promising but require further investigation. Current research gaps include comprehensive toxicological profiling and in vivo efficacy studies. Several research groups have indicated plans to explore these aspects in upcoming studies, which will be crucial for determining the compound's translational potential.

In conclusion, 2-chloro-1-(2,4-dihydroxyphenyl)ethan-1-one (CAS: 25015-92-3) represents an interesting chemical entity with multiple potential biomedical applications. Recent studies have expanded our understanding of its biological activities and synthetic accessibility. As research continues, this compound may serve as a valuable scaffold for the development of novel therapeutic agents targeting inflammation, oxidative stress, and potentially other disease pathways.

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