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4'-Methylacetophenone

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4'-Methylacetophenone Basic information
4'-Methylacetophenone Chemical Properties
Safety Information
  • Hazard Codes Xn
  • Risk Statements 36/37/38-22-20/21/22
  • Safety Statements 26-27-37/39-24/25-23-36
  • RIDADR UN 1325 4.1/PG 2
  • WGK Germany 3
  • RTECS AM9463000
  • TSCA Yes
  • HS Code 29143900
  • ToxicityLD50 orally in Rabbit: 1400 mg/kg LD50 dermal Rabbit > 2000 mg/kg
MSDS
4'-Methylacetophenone Usage And Synthesis
  • Description4'-Methylacetophenone has a fruity, floral odor resembling acetophenone and a sweet, strawberry-like flavor. May be prepared by slow addition of acetyl chloride to a mixture of toluene and AlCl in an ice bath and under vacuum, maintaining the temperature at +5°C and then letting it increase to +20°C.
  • Chemical Properties4?-Methylacetophenone has a fruity, floral odor resembling acetophenone and a sweet, strawberry-like flavor.
  • Chemical Propertiesclear colourless to pale yellowish liquid
  • Chemical Properties4'-Methylacetophenone has been identified in Brazilian rosewood oil and in pepper. It occurs as colorless crystals with a floral, sweet odor that is milder than that of acetophenone. 4-Methylacetophenone is prepared from toluene and acetic anhydride or acetyl chloride by a Friedel–Crafts reaction. It is used for blossom notes in mimosaand hawthorn-type perfumes, especially soap perfumes.
  • OccurrenceReported found in the essential oil distilled from the wood of Myrocarpus fastigiatus, Myrocarpus frondo sus, Bois de Rose. Also reported found in sour cherry, orange and grapefruit peel oil, black currants, guava, peach, blackberry, celery, potato, tomato, mentha oils, pepper, parsley, smoked fish, cognac, parmesan cheese, cocoa, tea, soybean, cloudberry, mango, cauliflower, broccoli, rice bran, buckwheat, dried bonito, cherimoya, calabash nutmeg and mastic gum leaf oil, cooked cabbage, mandarin juice.
  • Uses4'-Methylacetophenone is a methylated acteophenone used in cosmetics and perfumery. The presence of 4'-Methylacetophenone has been shown to accelerate the photopolymerization of Methyl methacrylate.
  • PreparationBy slow addition of acetyl chloride to a mixture of toluene and AlCl in an ice bath and under vacuum, maintaining the temperature at +5°C and then letting it increase to +20°C.
  • Taste threshold valuesTaste characteristics at 20 ppm: sweet, creamy, fruity, cherry and heliotropine-like.
  • Synthesis Reference(s)Journal of the American Chemical Society, 110, p. 2560, 1988 DOI: 10.1021/ja00216a032
    Tetrahedron Letters, 27, p. 2965, 1986 DOI: 10.1016/S0040-4039(00)84691-2
  • Safety ProfileModerately toxic by ingestion. A human skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.
  • Purification MethodsImpurities, including the o-and m-isomers, are removed by forming the semicarbazone (m 212-213.5o) which, after repeated crystallisation, is hydrolysed to the ketone. [Brown & Marino J Am Chem Soc 84 1236 1962.] It can also be purified by distillation under reduced pressure, followed by low temperature crystallisation from isopentane. [Beilstein 7 IV 701.]
4'-Methylacetophenone Preparation Products And Raw materials
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