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

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

Uses

Used in Flavor and Fragrance Industry:
2'-Methylacetophenone is used as a flavoring agent for its sweet, hawthorn, powdery, anisic, coumarinic, phenolic, burnt, nutty, and honey aroma. It is particularly suitable for enhancing the taste and scent of various food products and beverages.
Used in the Perfumery Industry:
2'-Methylacetophenone is used as a fragrance ingredient to provide vanilla, cherry, almond, coumarin, and various nut nuances to perfumes and other scented products.
Used in the Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2'-Methylacetophenone, due to its diverse aroma profile, could potentially be used in the development of pharmaceutical products that require specific scents for various applications, such as masking unpleasant odors or providing a pleasant aroma to medications.

References

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

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 
• 75-16-1 methylmagnesium bromide 
• 7287-82-3 1-O-tolyl-ethanol 
• 102369-89-1 1-(2-methyl-cyclohexa-1,4-dienyl)-ethanone 
• 56-23-5 tetrachloromethane 
• 118-75-2 chloranil 
• 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 

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 
• 855163-43-8 2-cyano-3-o-tolyl-crotonic acid ethyl ester 
• 7287-83-4 2'-methylacetophenone 2,4-dinitrophenylhydrazone 
• 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 
• 25872-73-5 3-morpholin-4-yl-1-o-tolyl-propan-1-one 
• 5757-86-8 1-(2-methylphenyl)-1-ethanone N,N-dimethylhydrazone 
• 22817-18-1 o,o'-Dimethyl-chalcon 

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%.

Selective oxidation of alkenes to carbonyls under mild conditions

Herein, a practical and sustainable method for the synthesis of aldehydes, ketones, and carboxylic acids from an inexpensive olefinic feedstock is described. This transformation features very sustainable and mild conditions and utilizes commercially available and inexpensive tetrahydrofuran as the additive, molecular oxygen as the sole oxidant and water as the solvent. A wide range of substituted alkenes were found to be compatible, providing the corresponding carbonyl compounds in moderate-to-good yields. The control experiments demonstrated that a radical mechanism is responsible for the oxidation reaction.

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.

Method for preparing carbonyl compound through oxidative cleavage of visible light excitation aqueous solution quantum dot catalytic olefin compound

The invention provides a method for preparing carbonyl compounds through oxidative cleavage of a visible light excitation aqueous solution quantum dot catalytic olefin compound. Belong to photocatalysis synthesis technical field. To the method, an aqueous solution quantum dot is used as a photocatalyst, and an aqueous solution quantum dot activated molecular oxygen catalytic oxidation aromatic alkene compound is excited by visible light to be cracked to prepare a carbonyl compound. Low-loading capacity is used, a simple aqueous solution quantum dot is used as a catalyst, the yield of the carbonyl compound is high, TON more than ten millions are obtained. The reaction conditions are mild, water serves as a main solvent for the reaction, and the carbonyl compound can be obtained by catalytic olefin compound oxidation cracking without addition of a cocatalyst or the like. The method is simple to operate, wide in substrate range and low in cost.

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.

Method for oxidative cracking of compound containing unsaturated double bonds

The invention relates to a method for oxidative cracking of a compound containing unsaturated double bonds. The method comprises the following steps: (A) providing a compound (I) containing unsaturated double bonds, a trifluoromethyl-containing reagent and a catalyst, wherein the catalyst is shown as a formula (II): M(O)mL1yL2z (II), M, L1, L2, m, y, z, R1, R2 and R3 being defined in the specification; and (B) mixing the compound containing the unsaturated double bonds and the trifluoromethyl-containing reagent, and performing an oxidative cracking reaction on the compound containing the unsaturated double bonds in the presence of air or oxygen by using the catalyst to obtain a compound represented by formula (III),.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):

PhIO-Mediated oxidative dethioacetalization/dethioketalization under water-free conditions

Treatment of thioacetals and thioketals with iodosobenzene in anhydrous DCM conveniently afforded the corresponding carbonyl compounds in high yields under water-free conditions. The mechanistic studies indicate that this dethioacetalization/dethioketalization process does not need water and the oxygen of the carbonyl products comes from the hypervalent iodine reagent.

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.