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Cas Database

585-74-0

585-74-0

Identification

  • Product Name:Ethanone,1-(3-methylphenyl)-

  • CAS Number: 585-74-0

  • EINECS:209-561-8

  • Molecular Weight:134.178

  • Molecular Formula: C9H10O

  • HS Code:29143990

  • Mol File:585-74-0.mol

Synonyms:Acetophenone,3'-methyl- (8CI);1-(3-Methylphenyl)ethanone;1-(3-Tolyl)ethanone;1-Acetyl-3-methylbenzene;1-m-Tolylethanone;3-Acetyltoluene;3-Methylphenylmethyl ketone;3'-Methylacetophenone;Methyl 3-methylphenyl ketone;Methylm-tolyl ketone;NSC 46632;m-Methylacetophenone;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:3''-Methylacetophenone
  • Packaging:25g
  • Price:$ 185
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3'-Methylacetophenone >97.0%(GC)
  • Packaging:100mL
  • Price:$ 193
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3'-Methylacetophenone >97.0%(GC)
  • Packaging:25mL
  • Price:$ 67
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3'-Methylacetophenone
  • Packaging:25 g
  • Price:$ 141
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3′-Methylacetophenone 98%
  • Packaging:5g
  • Price:$ 64.4
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3′-Methylacetophenone 98%
  • Packaging:25g
  • Price:$ 234
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3′-Methylacetophenone 98%
  • Packaging:100g
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:3'-Methylacetophenone 97%
  • Packaging:100g
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:3'-Methylacetophenone 97%
  • Packaging:5g
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:3'-Methylacetophenone 97%
  • Packaging:25g
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Relevant articles and documentsAll total 174 Articles be found

Suga,T. et al.

, p. 1873 - 1876 (1972)

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

Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge

supporting information, p. 1372 - 1377 (2022/02/23)

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 electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

Li, Zhibin,Zhang, Yan,Li, Kuiliang,Zhou, Zhenghong,Zha, Zhenggen,Wang, Zhiyong

, p. 2134 - 2141 (2021/09/29)

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Dimensional Reduction of Eu-Based Metal-Organic Framework as Catalysts for Oxidation Catalysis of C(sp3)–H Bond

Yan, Jun,Yu, Wei-Dong,Zhang, Yin,Zhao, Cai-Feng

, (2021/12/27)

Developing new catalysts for highly selectivity and conversion of saturated C(sp3)–H bonds is of great significance. In order to obtain catalysts with high catalytic performance, six Eu-based MOFs with different structural characteristics were obtained by using europium ions and different organic acid ligands, namely Eu-1~Eu-6. Eu-1, Eu-2 and Eu-3 featured three-dimensional structures, while Eu-4 and Eu-5 featured two-dimensional structures. Differently, a one-dimensional chain structure of Eu-6 was obtained by changing the ligand. All the six MOFs were applied to the catalytic reaction of C(sp3)–H bond, and it was found that the catalytic effect was gradually enhanced with the decrease of dimension and the increase of the size of channels. As expected, Eu-6 showed the highest selectivity (~99%) and conversion (~99%). Moreover, catalytic cycling and stability tests showed Eu-6 can be a reliable catalyst.

Organotellurium-catalyzed oxidative deoximation reactions using visible-light as the precise driving energy

Deng, Xin,Qian, Rongrong,Zhou, Hongwei,Yu, Lei

supporting information, p. 1029 - 1032 (2020/10/23)

Irradiated by visible light, the recyclable (PhTe)2-catalyzed oxidative deoximation reaction could occur under mild conditions. In comparison with the thermo reaction, the method employed reduced catalyst loading (1 mol% vs. 2.5 mol%), but afforded elevated product yields with expanded substrate scope. This work demonstrated that for the organotellurium-catalyzed reactions, visible light might be an even more precise driving energy than heating because it could break the Te–Te bond accurately to generate the active free radical catalytic intermediates without damaging the fragile substituents (e.g., heterocycles) of substrates. The use of O2 instead of explosive H2O2 as oxidant affords safer reaction conditions from the large-scale application viewpoint.

Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water

Du, Dongdong,Luo, Junfei,Shi, Sanshan,Xie, Pan,Xue, Cheng

, p. 5936 - 5943 (2021/08/23)

With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.

Process route upstream and downstream products

Process route

acetic anhydride
108-24-7

acetic anhydride

1-(4-methylphenyl)butan-1,3-dione
4023-79-4

1-(4-methylphenyl)butan-1,3-dione

para-methylacetophenone
122-00-9

para-methylacetophenone

2-Methylacetophenone
577-16-2,122382-54-1

2-Methylacetophenone

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
With acetic acid; at 120 ℃; under 1500.15 Torr; Time; Inert atmosphere;
acetyl chloride
75-36-5

acetyl chloride

para-methylacetophenone
122-00-9

para-methylacetophenone

2-Methylacetophenone
577-16-2,122382-54-1

2-Methylacetophenone

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
gallium(III) triflate; In nitromethane; at 25 ℃; for 11.6667h; Yield given;
With rhenium(I) pentacarbonyl bromide; at 120 ℃; for 2h;
tricarbonyl(η(6)-toluene)chromium
12083-24-8

tricarbonyl(η(6)-toluene)chromium

para-methylacetophenone
122-00-9

para-methylacetophenone

2-Methylacetophenone
577-16-2,122382-54-1

2-Methylacetophenone

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
With aluminium trichloride; acetyl chloride; In dichloromethane;
With aluminium trichloride; acetyl chloride; In carbon disulfide;
With acetylchloride; AlCl3; In carbon disulfide;
With acetylchloride; AlCl3; In dichloromethane;
acetic anhydride
108-24-7

acetic anhydride

para-methylacetophenone
122-00-9

para-methylacetophenone

2-Methylacetophenone
577-16-2,122382-54-1

2-Methylacetophenone

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
H-Beta zelite CP811; at 150 ℃; Further Variations:; Catalysts; Temperatures; Product distribution;
With ruthenium sulfate; zirconium(IV) oxide; at 110 ℃; for 2h; Further Variations:; Reagents; Product distribution;
With N-ethyl-pyridinium tetrafluoroborate; iron(III) chloride; at 20 ℃; for 4h; Further Variations:; Temperatures; Reagents; Catalysts; Product distribution;
acetic acid
64-19-7,77671-22-8

acetic acid

para-methylacetophenone
122-00-9

para-methylacetophenone

2-Methylacetophenone
577-16-2,122382-54-1

2-Methylacetophenone

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
In various solvent(s); at 25 ℃; for 2h; Yield given. Yields of byproduct given; solvent: CF3SO3H;
Sulfate; zirconium(IV) oxide; at 280 ℃; Product distribution; also with other acylating reagents;
Acetyl bromide
506-96-7

Acetyl bromide

para-methylacetophenone
122-00-9

para-methylacetophenone

2-Methylacetophenone
577-16-2,122382-54-1

2-Methylacetophenone

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
With iron(II) sulfate; for 2h; Product distribution; Ambient temperature; other aromatic hydrocarbon, acetylating reagents, catalyst, reaction times and temperature;
2%
1%
97%
1-<i>m</i>-tolyl-ethanone oxime
23040-54-2

1-m-tolyl-ethanone oxime

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
With magnesium hydrogen sulfate; water; silica gel; In hexane; for 0.5h; Heating;
95%
With diphenyl ditelluride; oxygen; In acetonitrile; for 24h; Irradiation;
95%
With ferrous(II) sulfate heptahydrate; benzyl seleninic acid; In ethyl acetate; at 60 ℃; for 24h; Green chemistry;
91%
With silica chromate; silica gel; for 0.0333333h; microwave irradiation;
82%
With oxygen; pivalaldehyde; (NMe4)2[Ni(Me2opba)]*4H2O; In fluorobenzene; at 20 ℃; for 4h;
60%
With dibenzyl diselenide; dihydrogen peroxide; In acetonitrile; at 60 ℃; for 24h;
58%
3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
With [(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine)RuCl2(PPh3)]; potassium tert-butylate; acetone; In methanol; at 56 ℃; for 0.0833333h; under 750.075 Torr; Catalytic behavior; Inert atmosphere;
99%
With C53H46ClN3P2Ru; potassium tert-butylate; acetone; at 56 ℃; for 0.0833333h; under 750.075 Torr;
98%
With potassium tetrakis-μ-pyrophosphitodiplatinate(II); tetrabutyl-ammonium chloride; In dichloromethane; water; at 20 ℃; for 8h; Inert atmosphere; Irradiation;
98%
With cobalt(III) acetate; sodium bromide; In acetic acid; at 50 ℃; for 2h;
97%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; sodium chloride; In neat (no solvent); Milling; Green chemistry;
96%
With C55H49N4OP2Ru; In toluene; under 750.075 Torr; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;
94%
1-(m-methylphenyl)ethanol; With ammonium tungstate; In water; at 20 ℃; for 0.25h; Green chemistry;
With dihydrogen peroxide; In water; at 70 ℃; for 11h; Green chemistry;
94%
With caesium fluoroxysulphate; In acetonitrile; at 30 - 35 ℃; for 1h;
93%
With [Cu6(pyridine-2-thiolate)6]; potassium hydroxide; In toluene; at 70 ℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere;
93%
With [Cu6(SC5H4N)6]; potassium hydroxide; In toluene; at 70 ℃; for 24h; Glovebox; Inert atmosphere;
93%
With 2,6-dimethylpyridine; 9-azabicyclo<3.3.1>nonane-N-oxyl; sodium perchlorate; In acetonitrile; for 8.66h; Inert atmosphere; Electrochemical reaction;
93%
With alumina supported chromium(VI) oxide; In hexane; for 24h; Ambient temperature;
92%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide; In water; at 100 ℃; for 8h; Sealed tube; Green chemistry;
90%
With caesium carbonate; In toluene; at 110 ℃; for 18h;
87%
With tert.-butylhydroperoxide; at 70 ℃; for 8h; Catalytic behavior;
86.2%
With oxygen; C26H21BrO; In dichloromethane; for 12h; Irradiation;
86%
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); In toluene; at 120 ℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;
83%
With C19H26IrN3O2(2+)*2CF3O3S(1-); In water; for 20h; Reflux;
81%
With C19H20IrNO2; sodium hydroxide; In water; at 140 ℃; for 48h; Inert atmosphere;
79%
With NADH oxidase; NAD; alcohol dehydrogenase from Candida parapsilosis-W286A mutant; In aq. acetate buffer; at 30 ℃; for 24h; pH=8; Reagent/catalyst; Green chemistry; Enzymatic reaction;
79%
Cp(*)Ir(κ1-2-hydroxypyridine)Cl2; In toluene; for 20h; Heating;
75%
With 1,10-Phenanthroline; iron(III)-acetylacetonate; potassium carbonate; In toluene; for 48h; Reflux; Green chemistry;
70%
With indium(III) triflate; chloroamine-T; In acetonitrile; for 2h; Reflux; Inert atmosphere;
70%
With chromium(III) oxide; sulfuric acid;
With chloroform; dinitrogen tetraoxide;
With styrene; 2C13H8NS(1-)*C12H27P*Ir(3+)*CF3O3S(1-); potassium tert-butylate; In toluene; at 110 ℃; for 12h; Schlenk technique; Inert atmosphere;
92 %Chromat.
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); In tert-Amyl alcohol; for 6h; Reflux;
With C66H60Cl2N10P2Ru2(2+)*2Cl(1-); potassium tert-butylate; In toluene; for 24h; Reflux; Inert atmosphere; Schlenk technique;
97 %Chromat.
With sulfuric acid; MnII((1R,2R)-N,N'-dimethyl-N,N'-bis-(phenyl-2-pyridinylmethyl)cyclohexane-1,2-diamine)(OTf)2; dihydrogen peroxide; In water; acetonitrile; at 25 ℃; for 1h; Inert atmosphere; Schlenk technique;
72 %Chromat.
With C21H25ClIrN4O(1+)*CF3O3S(1-); In 1,2-dichloro-benzene; at 150 ℃; for 12h; Inert atmosphere;
With C38H61N5OsP2; In toluene; at 100 ℃; for 24h; Schlenk technique;
63 %Chromat.
With C44H51IrN9OsP; In toluene; at 100 ℃; for 18h; Schlenk technique;
77 %Spectr.
With manganese(IV) oxide; silica gel; In acetonitrile; at 70 ℃; for 8h; Molecular sieve;
With tert.-butylhydroperoxide; 2C5H3N2O2(1-)*4.5C4H4N2*H(1+)*Cu(2+)*5Cu(1+)*6H2O*O62P2W18(6-); In acetonitrile; at 60 ℃; for 3h;
85 %Chromat.
With chromium(VI) oxide;
With C25H16N2O10Ru3; sodium carbonate; acetone; at 60 ℃; for 8h; Inert atmosphere; Schlenk technique;
90 %Chromat.
With sodium hypochlorite; potassium bromide; In dichloromethane; water; at 0 ℃; for 10h;
With tert.-butylhydroperoxide; C6H7As4N4O140Ru4W40(20-)*4K(1+)*9Na(1+)*7H(1+)*42H2O; In water; at 20 ℃; for 4h;
98 %Chromat.
With C20H24ClIrN2; sodium t-butanolate; In toluene; at 80 ℃; for 6h; Inert atmosphere; Schlenk technique;
93 %Chromat.
m-tolylboronic acid
17933-03-8

m-tolylboronic acid

acetic anhydride
108-24-7

acetic anhydride

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
With 2C60H80NaO12(2+)*Cl6Pd2(2-); potassium hydrogencarbonate; triphenylphosphine; In toluene; at 110 ℃; for 3h; Inert atmosphere;
76%
chloro(ethylene)rhodium(I) dimer; In 1,4-dioxane; for 16h; Heating;
68%
m-tolylboronic acid
17933-03-8

m-tolylboronic acid

acetonitrile
75-05-8,26809-02-9

acetonitrile

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
Conditions Yield
With [2,2]bipyridinyl; palladium diacetate; trifluoroacetic acid; In tetrahydrofuran; water; at 80 ℃; for 36h; Schlenk technique; Inert atmosphere;
83%

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