577-16-2

Basic information

• Product Name: 2'-Methylacetophenone
• Synonyms: 2-ACETYLTOLUENE;2'-METHYLACETOPHENONE;2-METHYLACETOPHENONE;1-METHYL-2-ACETYLBENZENE;O-METHYLACETOPHENONE;O-ACETYLTOLUENE;2'-Methylacetophenone 2-Acetyltoluene;Ethanone, 1-(2-methylphenyl)- (9CI)
• CAS NO: 577-16-2
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• EINECS: 209-408-5
• Product Categories: ACETYLGROUP;Building Blocks;C9;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 577-16-2.mol
• Article Data: 217

Chemical Properties

• Melting Point: 107-108 °C
• Boiling Point: 214 °C(lit.)
• Flash Point: 168 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.026 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5318(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: Soluble in ethanol. Insoluble in water.
• BRN: 907005
• CAS DataBase Reference: 2'-Methylacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Methylacetophenone(577-16-2)
• EPA Substance Registry System: 2'-Methylacetophenone(577-16-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 577-16-2(Hazardous Substances Data)

Usage

Description

2’-methylacetophenone is a colorless to pale yellow clear liquid. It has sweet, hawthorn, powdery, anisic, coumarinic, phenolic, burnt, nutty, honey aroma. It is used as an odor and/or flavor in acacia, butterscotch, black currant, grape, vanilla, etc.

References

[1] George A. Burdock, Fenaroli’s Handbook of Flavor Ingredients, Sixth Edition, 2010

Chemical Properties

Colorless to pale yellow clear liquid; sweet, hawthorn, powdery, anisic, coumarinic, phenolic, burnt, nutty, honey aroma.

Uses

2'-Methylacetophenone is possiblely used in Vanilla, cherry, almond, coumarin and various nut nuances.

Definition

ChEBI: 2'-methylacetophenone is a member of the class of acetophenones that is acetophenone which is substituted by a methyl group at position 2. It has a role as a fungal metabolite, an acaricide and a flavouring agent. It is a member of acetophenones and a member of toluenes.

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 943, 1983 DOI: 10.1021/ja00342a050

InChI:InChI=1/C9H10O/c1-7-5-3-4-6-9(7)8(2)10/h3-6H,1-2H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 529-19-1 2-Methylbenzonitrile 
• 7399-49-7 1-methyl-2-(prop-1-en-2-yl)benzene 
• 932-31-0 ortho-tolylmagnesium bromide 
• 75-07-0 acetaldehyde 
• 118-90-1 ortho-methylbenzoic acid 
• 64-19-7 acetic acid 
• 141-78-6 ethyl acetate 
• 933-88-0 ortho-toluoyl chloride 
• 75-36-5 acetyl chloride 
• 6921-34-2 benzylmagnesium chloride 
• 292-64-8 Cyclooctan 
• 13387-56-9 2-(o-tolyl)propyl-2-hydroperoxide 
• 19164-60-4 7-methylbicyclo[4.2.0]octa-1,3,5-trien-7-ol 

Downstream Products

• 13565-43-0 1-(2-methyl-phenyl)-3-phenyl-2-propen-1-one 
• 100994-06-7 (E)-ethyl 3-(2-methylphenyl)-but-2-enoate 
• 5330-79-0 4-(2-methylphenyl)-1,3-thiazol-2-amine 
• 4379-18-4 (2-methyl-2-o-tolyl-[1,3]dioxolan-4-yl)-methanol 
• 7572-79-4 2-(2-methylphenyl)propan-2-ol 
• 807285-55-8 3-pyrrolidino-1-o-tolyl-propan-1-one 
• 46274-54-8 3-(dimethylamino)-1-(o-tolyl)propan-1-one 
• 16882-28-3 1-o-tolyl-ethanone semicarbazone 
• 122-00-9 para-methylacetophenone 
• 5757-86-8 1-(2-methylphenyl)-1-ethanone N,N-dimethylhydrazone 
• 2919-19-9 1-methyl-2-[1-(2-methylphenyl)vinyl]benzene 
• 947-77-3 1-methyl-2-(1-phenylvinyl)benzene 
• 10228-87-2 (2,6-Dimethyl-phenyl)-[1-o-tolyl-eth-(E)-ylidene]-amine 
• 118540-57-1 3-(2-methylbenzoyl)acrylic acid 

Relevant articles and documents

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis

A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.

Visible-Light-Driven Oxidative Cleavage of Alkenes Using Water-Soluble CdSe Quantum Dots

The oxidative cleavage of C=C bonds is an important chemical reaction, which is a popular reaction in the photocatalytic field. However, high catalyst-loading and low turnover number (TON) are general shortcomings in reported visible-light-driven reactions. Herein, the direct oxidative cleavage of C=C bonds through water-soluble CdSe quantum dots (QDs) is described under visible-light irradiation at room temperature with high TON (up to 3.7×104). Under the same conditions, water-soluble CdSe QDs could also oxidize sulfides to sulfoxides with 51–84 % yields and TONs up to 3.4×104. The key features of this photocatalytic protocol include high TONs, wide substrates scope, low catalyst loadings, simple and mild reaction conditions, and molecular O2 as the oxidant.