14293-24-4

Basic information

• Product Name: 2,5-DIMETHOXYPHENYLACETONE
• Synonyms: 1-(2,5-Dimethoxyphenyl)acetone;2,5-DIMETHOXYPHENYLACETONE;1-(2,5-Dimethoxyphenyl)-2-propanone;Methyl 2,5-dimethoxybenzyl ketone;1-(2,5-dimethoxyphenyl)propan-2-one
• CAS NO: 14293-24-4
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• Product Categories: Aromatic Ketones (substituted)
• Mol File: 14293-24-4.mol

Chemical Properties

• Boiling Point: 290.1°C at 760 mmHg
• Flash Point: 120.1°C
• Appearance: /
• Density: 1.056g/cm³
• Vapor Pressure: 0.00211mmHg at 25°C
• Refractive Index: 1.497
• CAS DataBase Reference: 2,5-DIMETHOXYPHENYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHOXYPHENYLACETONE(14293-24-4)
• EPA Substance Registry System: 2,5-DIMETHOXYPHENYLACETONE(14293-24-4)

Safety Data

• Hazardous Substances Data: 14293-24-4(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
2,5-DIMETHOXYPHENYLACETONE is used as a synthetic musk and floral note for its sweet, floral odor, adding depth and complexity to fragrances.
Used in Pharmaceutical Industry:
2,5-DIMETHOXYPHENYLACETONE is used as a precursor in the synthesis of various pharmaceuticals and organic compounds, contributing to the development of new medications and chemical products.

InChI:InChI=1/C11H14O3/c1-8(12)6-9-7-10(13-2)4-5-11(9)14-3/h4-5,7H,6H2,1-3H3

Upstream product

• 1758-25-4 (2,5-dimethoxyphenyl)acetic acid 
• 18790-57-3 (E)-1,4-dimethoxy-2-(2-nitroprop-1-en-1-yl) benzene 
• 25245-34-5 1-bromo-2,5-dimethoxybenzene 
• 78-95-5 chloroacetone 
• 67-64-1 acetone 
• 150-78-7 1,4-dimethoxybezene 
• 40180-96-9 2-(β-hydroxypropyl)-1,4-dimethoxybenzene 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 134040-27-0 2,5-dimethoxy-β-methyl-β-nitrostyrene 

Downstream Products

• 43021-98-3 3-(2,5-dimethoxyphenyl)-2-oximinopropane 
• 67707-78-2 N,N-dimethyl-2-(2,5-dimethoxyphenyl)isopropylamine 
• 86432-48-6 4-(2,5-Dimethoxy-phenyl)-3-hydroxy-3-methyl-butyric acid ethyl ester 
• 152093-84-0 3-(2,5-dimethoxyphenyl)-2-propylidenemalononitrile 
• 170753-14-7 3-(2',5'-dimethoxyphenyl)butan-2-one 
• 6769-56-8 2-methyl-5-hydroxy-benzofuran 
• 170753-16-9 6-(2',5'-dimethoxyphenyl)-3-methoxy-6-methylcyclohex-2-enone 
• 170753-15-8 4-(2,5-Dimethoxy-phenyl)-4-methyl-cyclohexane-1,3-dione 
• 195001-15-1 4-(2,5-Dimethoxy-phenyl)-4-methyl-3-(1-trimethylsilanyl-vinyl)-cyclohex-2-enone 
• 152093-90-8 2-amino-3-cyano-5-(2',5'-dimethoxyphenyl)-4-methylthiophene 
• 1188412-59-0 (R)-1-(2,5-dimethoxyphenyl)propan-2-ol 
• 609771-69-9 (2S)-1-(2,5-dimethoxyphenyl)-2-propanol 

Relevant articles and documents

Enantioselective Formal Synthesis of the Cytotoxic Topoisomerase II Inhibitor Deoxythysanone, Catalyzed by Chiral Spiroborate Ester

Abstract: Bioactive pyranonaphthoquinone analogs, (1R,3S)-deoxythysanone,(1R,3S)-thysanone, and (1R,3S)-demethoxythysanone can be efficientlysynthesized from a common intermediate product, (S)-3-methyl-3,4-dihydro-1H-isochromene-5,8-dione. We have develop

Pigments of Fungi. LIX - Synthesis of (1S,3S)- and (1R,3R)-austrocortilutein and (1S,3S)-austrocortirubin from citramalic acid

The naturally occurring tetrahydroanthraquinone (1S,3S)-austrocortilutein (1) is synthesized for the first time in enantiomerically pure form by Diels-Alder cycloaddition between the functionalized butadiene derivative (8) and the chiral 1,3-dihydroxy-1,2,3,4-tetrahydro-5,8-naphthoquinone (9), the latter being derived from (R)-citramalic acid (3). The natural products (1S,3S)-austrocortirubin (2) and (1R,3R)-austrocortilutein (5) were also prepared for the first time by using the same strategy. CSIRO 2000.

Use of conjugated dienones in cyclialkylations: Total syntheses of arucadiol, 1,2-didehydromiltirone, (±)-hinokione, (±)-nimbidiol, sageone, and miltirone

Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.

Nickel-catalyzed direct electrochemical cross-coupling between aryl halides and activated alkyl halides

The electrochemical reduction of a mixture of aryl halides and activated alkyl halides in DMF in the presence of catalytic amount of NiBr2bipy leads to cross-coupling products in good to high yields. The method applies to the synthesis of α-aryl ketones, α-aryl esters, and allylated compounds from readily available organic halides. Optimization of the process has been obtained by slowly adding the most reactive organic halide (usually the activated alkyl halide) during the electrolysis which is best conducted at 70 °C when aryl bromides are involved.

A novel method of arylation of α-chloroketones

α-Arylated ketones were obtained in moderate to good yields by one-step electroreductive coupling of α-chloroketones and arylhalides in DMF and in the presence of a Al- or Zn-sacrificial anode and a catalytic amount of a nickel complex.

2,4-Diaminothienopyrimidine Analogues of Trimetrexate and Piritrexim as Potential Inhibitors of Pneumocystis Carinii and Toxoplasma gondii Dihydrofolate Reductase

A series of eight previously undescribed 2,4-diaminothienopyrimidine analogues of the potent dihydrofolate reductase (DHFR) inhibitors trimetrexate (TMQ) and piritrexim (PTX) were synthesized as potential drugs against Pneumocystis carinii and Toxoplasma gondii, which are major causes of severe opportunistic infections in AIDS patients. 2,4-Diamino-5-methyl-6-(aryl/aralkyl)thienopyrimidines with 3,4,5-trimethoxy or 2,5-dimethoxy substitution in the aryl/aralkyl moiety and 2,4-diamino-5-(aryl/aralkyl)thienopyrimidines with 2,5-dimethoxy substitution in the aryl/aralkyl moiety were obtained by reaction of the corresponding 2-amino-3-cyanothiophenes with chloroformamidine hydrochloride.The aryl group in the 5,6-disubstituted analogues was either attached directly to the hetero ring or was separated from it by one or two carbons, whereas the aryl group in the 5-monosubstituted analogues was separated from the hetero ring by two or three carbons. 2-Amino-3-cyano-5-methyl-6-(aryl/alkyl)thiophene intermediates for the preparation of the 5,6-disubstituted analogues were prepared from ω-aryl-2-alkylidenemalononitriles and sulfur in the presence of a secondary amine, and 2-amino-3-cyano-4-(aryl/aralkyl)thiophene intermediates for the preparation of the 5-monosubstituted analogues were obtained from ω-aryl-1-chloro-2-alkylidenemalononitriles and sodium hydrosulfide.Synthetic routes to the heterofore unknown ylidenemalononitriles, and the ketone precursors thereof, were developed.The final products were tested in vitro as inhibitors of DHFR from Pneumocystis carinii, Toxoplasma gondii, rat liver, beef liver, and Lactobacillus casei.A select number of previously known 2,4-diaminothienopyrimidines lacking the 3,4,5-trimethoxyphenyl and 2,5-dimethoxyphenyl substitution pattern of TMQ and PTX, respectively, were also tested for comparison.None of the compounds was as potent as TMQ or PTX, and while some of them showed some selectivity in their binding to Pneumocystis carinii and Toxoplasma gondii versus rat liver DHFR, this effect was not deemed large enough to warrant further preclinical evaluation.

Novel Electrophilic Species Equivalent to α-Keto Cations. Reactions of O,O-Diprotonated Nitro Olefins with Benzenes Yield Arylmethyl Ketones

The N,N-dihydroxyiminium carbenium ions formed by O,O-diprotonation of nitro olefins in a strong acid, trifluoromethanesulfonic acid (TFSA), are discrete and novel dipositively charged species.The dications formed from α-substitited nitroethylenes are reactive electrophiles to give α-arylated ketones in high yields.This constitutes a versatile synthetic method for the preparation of α-arylated ketones, which are difficult to synthesize by the conventional Friedel-Crafts reactions.

A Novel Route to Arylacetones via a Masked α-Acylcarbonium Intermediate

The Ag+ induced aromatic substitution reaction of bromoacetone O-methyloxime is described.

Aromatic Acetonylation Promoted by Manganese(III) and Cerium(IV) Salts

Treatment of aromatic hydrocarbons with acetone and manganese(III) acetate gave rise to arylacetones in yields ranging from 25 percent with chlorobenzene to 74 percent with anisole.Cerium(IV) salts were also successfully used as promoters but gave lower yields.The reactions were relatively free of side products except with toluene.Isomer distributions, relative rates, and partial rate factors were determined for acetonylation of anisole, toluene, chlorobenzene, and fluorobenzene.A Hammett plot of the log of the partial rate factors for the manganese(III) system vs. ?-constants gave a slope, ρ, of -2.4 +/- 0.3.An isotope effect kH/kD = 3.8 was observed for the manganese(III)-promoted reaction with acetone-d6, indicating rate-determining proton loss from acetone.The overall mechanism involves formation and attack of acetonyl radicals onto the aromatic hydrocarbon followed by subsequent oxidative deprotonation of the resulting ?-radical complex.The acetonyl radical exhibits appreciable electron-deficient character in its substitution behavior with aromatic hydrocarbons.