Description

3-Methoxyacetophenone (CAS 586-37-8) is a high-purity aromatic ketone with the molecular formula C₉H₁₀O₂, widely utilized in organic synthesis and pharmaceutical research. This compound, also known as 1-(3-methoxyphenyl)ethanone, features a methoxy group at the meta position of the acetophenone backbone, offering unique reactivity for electrophilic substitution and carbonyl-based reactions. Available in >98% purity by GC, it is supplied as a clear to pale-yellow liquid with a characteristic aromatic odor, stabilized for long-term storage under inert conditions. Ideal for use as a flavor/fragrance intermediate, photoinitiator precursor, or ligand scaffold in catalytic systems. Packaged in amber glass bottles or sealed drums under nitrogen to prevent degradation.

Properties

• CAS Number: 586-37-8
• Complexity: 142
• IUPAC Name: 1-(3-methoxyphenyl)ethanone
• InChI: InChI=1S/C9H10O2/c1-7(10)8-4-3-5-9(6-8)11-2/h3-6H,1-2H3
• InChI Key: BAYUSCHCCGXLAY-UHFFFAOYSA-N
• Exact Mass: 150.068079557
• Molecular Formula: C9H10O2
• Molecular Weight: 150.17
• SMILES: CC(=O)C1=CC(=CC=C1)OC
• Topological: 26.3
• Monoisotopic Mass: 150.068079557
• Physical Description: Pale yellow liquid;
• Vapor Pressure: 0.08 [mmHg]
• Synonyms: 3′-Methoxyacetophenone, 586-37-8, 3-Methoxyacetophenone, 3-Acetylanisole, m-Methoxyacetophenone, 1-(3-METHOXYPHENYL)ETHANONE, Ethanone, 1-(3-methoxyphenyl)-, Acetophenone, m-methoxy-, NSC 65593, Acetophenone, 3′-methoxy-, 1K3UR56Z4N, EINECS 209-573-3, NSC-65593, AI3-26011, DTXSID10207321, RIVASTIGMINE HYDROGEN TARTRATE IMPURITY H [EP IMPURITY], RIVASTIGMINE HYDROGEN TARTRATE IMPURITY H (EP IMPURITY), mMethoxyacetophenone, 3’Methoxyacetophenone, Acetophenone, mmethoxy, Acetophenone, 3’methoxy, Ethanone, 1(3methoxyphenyl), Acetophenone, 3’methoxy (8CI), DTXCID10129812, Acetophenone, 3′-methoxy-(8CI), Ethanone, 1(3methoxyphenyl) (9CI), Ethanone, 1-(3-methoxyphenyl)-(9CI), 209-573-3, 1-(3-Methoxyphenyl)ethan-1-one, MFCD00008736, 1-(3-methoxy-phenyl)-ethanone, meta-Methoxyacetophenone, 1-Acetyl-3-methoxybenzene, m-Acetylanisole; m-Methoxyacetophenone, 3 inverted exclamation mark -Methoxyacetophenone, m-Acetanisole, 3-METHOXYACETOPHENONE (D3), UNII-1K3UR56Z4N, m-Acetylanisole, 3-acetanisole, 3-Acetoanisole, m-Metoxyacetophenone, m-Methoxy acetophenone, 3-methoxy acetophenone, 3?-Methoxyacetophenone, 3/’-Methoxyacetophenone, 3′-Methoxyacetophenone, 3-Methoxy-1-acetylbenzene, NCIOpen2_000067, SCHEMBL52445, Methyl 3-methoxyphenyl ketone, SCHEMBL221066, 1-(3-methoxyphenyl)-ethanone, 3′-Methoxyacetophenone, 97%, SCHEMBL1257984, SCHEMBL8319196, SCHEMBL8321846, 1-(3-Methoxyphenyl)ethanone #, CHEMBL5270199, SCHEMBL12015247, 1-[3-(methyloxy)phenyl]ethanone, NSC65593, SBB040249, STK802448, AKOS000119490, CS-W020599, FM34460, PS-5287, AC-10020, SY003673, DB-028538, m-Acetylanisole;1-(3-Methoxyphenyl)ethanone, M0104, NS00020529, ST50213410, EN300-16173, 3 inverted exclamation marka-Methoxyacetophenone, L10020, Q27252520, Z54179675, F0001-1530, m-Acetanisole; m-Acetylanisole; m-Acetylanisole; m-Acetanisole, InChI=1/C9H10O2/c1-7(10)8-4-3-5-9(6-8)11-2/h3-6H,1-2H

Application

3-Methoxyacetophenone serves as a key building block in pharmaceutical synthesis, particularly for nonsteroidal anti-inflammatory drugs (NSAIDs) and CNS-active compounds. Its electron-rich aromatic ring makes it valuable in palladium-catalyzed cross-coupling reactions for material science applications. The compound is also employed as a photoinitiator component in UV-curable coatings and as a flavoring agent in food chemistry due to its sweet, hawthorn-like aroma.

Safety and Hazards

GHS Hazard Statements

• H302 (35%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (35%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (40%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (10%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
• H412 (15%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (35%)
• Skin Irrit. 2 (35%)
• Eye Irrit. 2A (40%)
• STOT SE 3 (10%)
• Aquatic Chronic 3 (15%)

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