4'-Methylacetophenone

4'-Methylacetophenone Basic information
Product Name:4'-Methylacetophenone
Synonyms:Acetophenone, 4'-methyl-;Esberiven;Ethanone,1-(4-methylphenyl)-;Melilot;Melilotal;p-Acetotoluene;Sweet clover;Yellow melilot
CAS:122-00-9
MF:C9H10O
MW:134.18
EINECS:204-514-8
Product Categories:Ketones;Acetophenones (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Aromatics;Acetophenone series;ACETYLGROUP;Benzene derivatives;Aromatic Acetophenones & Derivatives (substituted);Organics;Celecoxib;122-00-9;bc0001
Mol File:122-00-9.mol
4'-Methylacetophenone Structure
4'-Methylacetophenone Chemical Properties
Melting point 22-24 °C (lit.)
Boiling point 226 °C (lit.)
density 1.004 g/mL at 20 °C 1.005 g/mL at 25 °C (lit.)
vapor pressure 0.52 hPa (25 °C)
refractive index n20/D 1.533(lit.)
FEMA 2677 | 4'-METHYLACETOPHENONE
Fp 198 °F
storage temp. Store below +30°C.
solubility 2.07g/l
form Liquid
color Clear colorless to pale yellow
Odorat 10.00 % in dipropylene glycol. hawthorn sweet mimosa coumarin cherry acetophenone
Odor Typefloral
explosive limit1.00%(V)
Water Solubility 0.37 g/L (15 ºC)
JECFA Number807
BRN 606053
InChIKeyGNKZMNRKLCTJAY-UHFFFAOYSA-N
LogP2.1 at 25℃
CAS DataBase Reference122-00-9(CAS DataBase Reference)
NIST Chemistry ReferenceEthanone, 1-(4-methylphenyl)-(122-00-9)
EPA Substance Registry SystemEthanone, 1-(4-methylphenyl)- (122-00-9)
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 Information
ProviderLanguage
p-Methylacetophenone English
SigmaAldrich English
ACROS English
ALFA English
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 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.
Uses4'-Methylacetophenone is used as a flavoring agent. It reacts with morpholine to get 4-(p-tolyl-thioacetyl)-morpholine in the presence of sulfur as a reagent. Further, it is used as an intermediate in the manufacture of active pharmaceutical ingredients, perfumes and cosmetics.
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.
DefinitionChEBI: 4'-Methylacetophenone is an aromatic ketone. It is a metabolite found in or produced by Saccharomyces cerevisiae.
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
General Description4′-Methylacetophenone is a clear colourless to pale yellowish liquid that occurs naturally in mango, tomato and orange.
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'-Methoxyacetophenone 2-Bromo-4'-methylacetophenone Methyl Emodin 3'-METHYLACETOPHENONE,3-METHYLACETOPHENONE,3'-METHYLACETOPHENONE (M-) 4-Nitroacetophenone Acetophenone 4'-Hydroxyacetophenone 2-BROMO-4'-PHENYLACETOPHENONE Thiophanate-methyl 3'-(Trifluoromethyl)acetophenone 2-Acetylfluorene 4-(TRIFLUOROMETHYL)BENZOPHENONE Methyl bromide 4-Aminoacetophenone ALIZARIN COMPLEXONE 2'-METHYLACETOPHENONE,2-METHYLACETOPHENONE 4'-(Trifluoromethyl)acetophenone

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