1-(4-Chloro-2-hydroxyphenyl)-2,2,2-trifluoroethanone (also known as 4‘-chloro-2’-hydroxy-2,2,2-trifluoroacetophenone) is a functionalized aromatic ketone featuring a trifluoromethyl ketone moiety at the 1-position of an electron-rich 4-chloro-2-hydroxyphenyl ring, where the ortho-hydroxy group and the powerful electron-withdrawing trifluoromethyl group work in tandem to create a highly polarized, hydrogen-bond-donating platform for diverse synthetic transformations.
1-(4-Chloro-2-hydroxyphenyl)-2,2,2-trifluoroethanone (CAS 2229260-52-8) is a functionalized aromatic ketone that serves as a key building block in medicinal chemistry and organic synthesis. The molecule features a 4-chloro-2-hydroxyphenyl group attached to a trifluoromethyl ketone, with a molecular formula of C₈H₄ClF₃O₂ and a molecular weight of 224.56 g/mol.
In pharmaceutical applications, 1-(4-Chloro-2-hydroxyphenyl)-2,2,2-trifluoroethanone is used as a key intermediate in the synthesis of pharmaceuticals, particularly in the production of non-steroidal anti-inflammatory drugs (NSAIDs) and other bioactive molecules. Its structure supports the introduction of trifluoromethyl and chloro groups, which can enhance metabolic stability and binding affinity in drug candidates. The compound has also been investigated in the context of hydroxyphenyl derivatives for biological applications, including as potential anti-bacterial and anti-parasitic agents.
In organic synthesis, 1-(4-Chloro-2-hydroxyphenyl)-2,2,2-trifluoroethanone is commonly employed for building complex aromatic ketones with fluorinated moieties. It is also utilized in the development of agrochemicals due to its reactivity and functional group compatibility. Additionally, related trifluoroacetophenone derivatives have been described in patents as reagents for trifluoroethanolation or difluoroethanolation, serving as synthetic intermediates for numerous organic compounds, some of which possess pharmaceutical activity.
Product Parameters
Parameter
Specification
CAS Number
2229260-52-8
Molecular Formula
C₈H₄ClF₃O₂
Molecular Weight
224.56 g/mol
MDL Number
MFCD31922518
Canonical SMILES
ClC1C([H])=C([H])C(C(C(F)(F)F)=O)=C(C=1[H])O[H]
Purity
≥95% commercially available; ≥98% available upon request
Appearance
Solid (white to off-white powder)
Boiling Point
247.7 ± 35.0 °C (Predicted)
Density
1.520 ± 0.06 g/cm³ (Predicted)
Flash Point
108.8 ± 25.9 °C (Predicted)
Safety Precautions
Avoid breathing dust/fume/gas/mist/vapours/spray. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of water. If skin irritation occurs: Get medical advice/attention. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice/attention
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Dual Quality Grades
Both research/pharma grade(≥98%)and high-purity impurity grade(≥99%)available to meet diverse customer needs.
Storage Conditions
● Temperature: Sealed in dry, room temperature (15–25 °C); store under inert gas (nitrogen or argon) recommended
● Container: Airtight, tightly sealed container
● Protection: Store away from moisture, light, and strong oxidizing agents
● Desiccation: Keep in a dry environment; the compound may be hygroscopic
● Stability: Stable under recommended storage conditions for up to 24 months
● Incompatibilities: Strong oxidizing agents, strong bases, and strong acids
Safety Notice: The compound is classified as an irritant (H315 – Skin Irritation, H319 – Eye Irritation, H335 – Respiratory Irritation). Use appropriate PPE (gloves, goggles, lab coat), avoid generating dust, and work in a well-ventilated area. Avoid breathing dust/fume/gas/mist/vapours/spray. In case of skin contact, wash with plenty of water; if skin irritation occurs, get medical advice/attention. In case of eye contact, rinse cautiously with water for several minutes, remove contact lenses if present and easy to do, continue rinsing; if eye irritation persists, seek medical advice. Dispose of in accordance with local regulations.
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