Description

2-Chloro-1-(4-methoxyphenyl)ethanone (CAS No. 2196-99-8) is a high-purity organic compound with the molecular formula C₉H₉ClO₂. This crystalline solid is a versatile building block in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its structure features a reactive chloroacetyl group adjacent to a methoxy-substituted aromatic ring, making it an excellent electrophile for nucleophilic substitution reactions. The compound is characterized by its high stability under standard storage conditions and is typically supplied as a white to off-white powder with ≥98% purity (HPLC). Suitable for use in research laboratories and industrial-scale applications, it is packaged under inert gas to ensure long-term stability. Always handle with appropriate personal protective equipment (PPE) due to its potential irritant properties.

Properties

• CAS Number: 2196-99-8
• Complexity: 151
• IUPAC Name: 2-chloro-1-(4-methoxyphenyl)ethanone
• InChI: InChI=1S/C9H9ClO2/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-5H,6H2,1H3
• InChI Key: MCRINSAETDOKDE-UHFFFAOYSA-N
• Exact Mass: 184.0291072
• Molecular Formula: C9H9ClO2
• Molecular Weight: 184.62
• SMILES: COC1=CC=C(C=C1)C(=O)CCl
• Topological: 26.3
• Monoisotopic Mass: 184.0291072
• Synonyms: 2196-99-8, 2-chloro-1-(4-methoxyphenyl)ethanone, 2-chloro-1-(4-methoxyphenyl)ethan-1-one, DTXSID80862865, DTXCID20811574, 606-867-7, inchi=1/c9h9clo2/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-5h,6h2,1h, 4-Methoxyphenacyl chloride, 2-Chloro-4′-methoxyacetophenone, 2-Chloro-1-(4-methoxy-phenyl)-ethanone, MFCD00216508, 4-Methoxyphenacylchloride, ethanone, 2-chloro-1-(4-methoxyphenyl)-, 4′-METHOXY-2-CHLOROACETOPHENONE, 4-(CHLOROACETYL)ANISOLE, NSC41670, p-Methoxyphenacyl chloride, SCHEMBL2314649, MCRINSAETDOKDE-UHFFFAOYSA-N, CK1193, NSC 41670, NSC-41670, SBB027247, STL195583, AKOS000112361, CS-W016981, SB35482, 2-chloro-1-(4-methoxyphenyl)-ethanone, 4′-Methoxy-2-chloroacetophenone, 97%, NCGC00660646-01, CS-13026, DB-045738, M3268, EN300-07125, AQ-917/42754012, Z56945957, F8889-9210

Application

2-Chloro-1-(4-methoxyphenyl)ethanone serves as a key intermediate in the synthesis of various bioactive molecules, including potential pharmaceutical candidates. Researchers utilize this compound in Friedel-Crafts acylation reactions to introduce the 4-methoxyphenacyl moiety into complex molecular architectures. It is particularly valuable in medicinal chemistry for the development of kinase inhibitors and other therapeutic agents. The chloroacetyl group also enables further functionalization through nucleophilic displacement reactions with amines, thiols, and other nucleophiles.

Safety and Hazards

GHS Hazard Statements

• H302 (53.1%): Harmful if swallowed [Warning Acute toxicity, oral]
• H314 (54.3%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statements

• P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (53.1%)
• Skin Corr. 1B (54.3%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.