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5337-93-9 Usage

Chemical Properties

clear light yellow liquid

Uses

Different sources of media describe the Uses of 5337-93-9 differently. You can refer to the following data:
1. 4'-methylpropiophenone has been reported to be used in the synthesis of pharmaceutical compounds such as tolperisone and other muscle relaxants. The substance is also a starting material in the synthesis of 4-methylmethcathinone (mephedrone). Mephedrone has been encountered as a ‘legal high’ and on the illicit drug market masquerading as cocaine (in powder form), MDMA (in tablet form) and as an adulterant. According to the 2016 European Drugs Market Report produced by the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA), mephedrone has created a specific demand and carved its own distinct market share.
2. 4′-Methylpropiophenone is a chemical reagent used in electrocarboxylation reactions.

Application

4′-Methylpropiophenone can be used as a building block to synthesize:N-(4-Chlorophenyl)-N′-[1-(4-methylphenyl)propyl]urea as a potential CRAC channel inhibitor.Mono and trinuclear cobaloxime/organocobaloxime complexes, which are used as efficient catalysts for the synthesis of cyclic carbonates.Tolperisone (TOL) via acid-catalyzed reaction with piperidine hydrochloride and 1,2-dioxolane.

Definition

ChEBI: 4-methylpropiophenone is an aromatic ketone that is propiophenone bearing a methyl group at C-4. It derives from a propiophenone.

Check Digit Verification of cas no

The CAS Registry Mumber 5337-93-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,3 and 7 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5337-93:
(6*5)+(5*3)+(4*3)+(3*7)+(2*9)+(1*3)=99
99 % 10 = 9
So 5337-93-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O/c1-3-10(11)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3

5337-93-9 Well-known Company Product Price

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  • Alfa Aesar

  • (B21673)  4'-Methylpropiophenone, 94%   

  • 5337-93-9

  • 100g

  • 253.0CNY

  • Detail
  • Alfa Aesar

  • (B21673)  4'-Methylpropiophenone, 94%   

  • 5337-93-9

  • 500g

  • 1147.0CNY

  • Detail

5337-93-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-methylpropiophenone

1.2 Other means of identification

Product number -
Other names 4-Methylpropiophenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5337-93-9 SDS

5337-93-9Synthetic route

1-p-tolyl-1-propanol
25574-04-3

1-p-tolyl-1-propanol

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With potassium hexafluorophosphate; tert.-butylnitrite; 9-azabicyclo<3.3.1>nonane-N-oxyl; oxygen In water at 60℃; under 2250.23 Torr; for 4.5h; Autoclave; Green chemistry;99%
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 Iron(III) nitrate nonahydrate; 9-azabicyclo<3.3.1>nonane-N-oxyl In acetonitrile at 20℃; for 8h;92%
1-(4-methylphenyl)-2-propen-1-ol
58824-48-9

1-(4-methylphenyl)-2-propen-1-ol

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With [Ru(η(3):η(3)-C10H16)Cl(O2CCH3)] In aq. phosphate buffer at 50℃; for 5h; pH=7; Sealed tube; Inert atmosphere;99%
With Fe(II)(bis(2-(diisopropylphosphino)ethyl)amine)(CO)(H)(Cl); potassium tert-butylate In toluene at 80℃; for 1h; Inert atmosphere;97%
With C30H29BrMnNO2P2; potassium tert-butylate In toluene at 120℃; for 1h;90%
C11H16O

C11H16O

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 24h;98%
1-(p-tolyl)propan-1-one oxime
54582-25-1, 54582-32-0, 59507-21-0

1-(p-tolyl)propan-1-one oxime

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With sodium nitrite In water; acetonitrile at 40℃; for 1h;97%
With Iron(III) nitrate nonahydrate; oxygen In toluene at 37℃; under 760.051 Torr; for 1.5h; Schlenk technique; Green chemistry;89%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Trametes versicolor laccase; water In acetonitrile at 20℃; for 12h; pH=5; Enzymatic reaction;
2-bromo-4'-methylpropiophenone
92821-88-0, 1451-82-7

2-bromo-4'-methylpropiophenone

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With bismuth(III) chloride; sodium tetrahydroborate In tetrahydrofuran for 4h; Ambient temperature;94.6%
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / Reflux
2: bis(pinacol)diborane; sodium t-butanolate; 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine cobalt(II)dichloride / tetrahydrofuran; methanol / 3 h / 65 °C / Schlenk technique; Inert atmosphere
View Scheme
p-allyltoluene
3333-13-9

p-allyltoluene

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; palladium diacetate; toluene-4-sulfonic acid In water; acetonitrile at 20℃; for 6h; Wacker Oxidation; chemoselective reaction;93%
sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

propiononitrile
107-12-0

propiononitrile

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; trifluoroacetic acid; 6-methyl-2,2'-bipyridine In tetrahydrofuran; water at 100℃; for 1h; Microwave irradiation;91%
propionic acid anhydride
123-62-6

propionic acid anhydride

toluene
108-88-3

toluene

A

2-methylpropiophenone
2040-14-4

2-methylpropiophenone

B

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
HZSM-5 at 250℃; for 12h; other catalyst: HY-Zeolite; Yield given;A n/a
B 90%
HZSM-5 at 250℃; for 12h; other catalyst: HY-Zeolite; Yields of byproduct given;A n/a
B 90%
With ruthenium sulfate; zirconium(IV) oxide at 110℃; for 2h; Product distribution; Further Variations:; Reagents;
2-phenoxy-1-(p-tolyl)propan-1-one
204908-05-4

2-phenoxy-1-(p-tolyl)propan-1-one

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine cobalt(II)dichloride; bis(pinacol)diborane; sodium t-butanolate In tetrahydrofuran; methanol at 65℃; for 3h; Schlenk technique; Inert atmosphere;90%
1-(1H-benzo[d][1,2,3]triazol-1-yl)propan-1-one
54264-50-5

1-(1H-benzo[d][1,2,3]triazol-1-yl)propan-1-one

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 1.5h;89%
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

propiononitrile
107-12-0

propiononitrile

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; sodium hydrogencarbonate In water at 100℃; for 5h; Autoclave;89%
propionyl chloride
79-03-8

propionyl chloride

tri(p-tolyl)bismuth
5142-75-6

tri(p-tolyl)bismuth

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With triethylamine; triphenylphosphine; palladium dichloride In 1,4-dioxane at 80℃; for 4h;88%
With triethylamine; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 3h;77%
propionyl chloride
79-03-8

propionyl chloride

pTolSnR3

pTolSnR3

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
Pd(phenylimino)acenaphthene dimethyl fumarate In N,N-dimethyl-formamide at 50℃; for 17h;85%
α-chloro-4-methyl propiophenone
69673-92-3

α-chloro-4-methyl propiophenone

A

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

B

(R,S)-2-(4'-methylphenyl) propionic acid
938-94-3

(R,S)-2-(4'-methylphenyl) propionic acid

Conditions
ConditionsYield
With methyloxirane In water; acetone Irradiation; pH neutral;A 5%
B 84%
1-(p-tolyl)cyclopropan-1-ol
40122-37-0

1-(p-tolyl)cyclopropan-1-ol

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; silver nitrate In water; acetone at 50℃; for 12h; Solvent;83%
ethyl bromide
74-96-4

ethyl bromide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
Stage #1: ethyl bromide With magnesium In tetrahydrofuran Inert atmosphere;
Stage #2: para-methylbenzonitrile With copper(l) iodide In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃;
80%
propionic acid
802294-64-0

propionic acid

toluene
108-88-3

toluene

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With polyphosphoric acid for 0.025h; Microwave irradiation;80%
triethyl borane
97-94-9

triethyl borane

S-2-(1-(methoxyimino)ethyl)phenyl 4-methylbenzothioate

S-2-(1-(methoxyimino)ethyl)phenyl 4-methylbenzothioate

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With Cu(I) 3-methylsalicylate In N,N-dimethyl-formamide for 1h; Microwave irradiation; Heating; Inert atmosphere; Sealed tube;80%
propionyl chloride
79-03-8

propionyl chloride

toluene
108-88-3

toluene

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With aluminium trichloride for 3h; Friedel-Crafts acylation; cooling;76%
With carbon disulfide; aluminium trichloride
With titanium tetrachloride
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

para-methylacetophenone
122-00-9

para-methylacetophenone

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With ammonium peroxydisulfate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 110℃; for 3h; Inert atmosphere; Sealed tube;76%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-(toluene-4-sulfonyl)-1-p-tolylethanone
61820-95-9

2-(toluene-4-sulfonyl)-1-p-tolylethanone

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) diiodide; tricyclohexylphosphine In tetrahydrofuran at 80℃; Kumada Cross-Coupling; Inert atmosphere;75%
4-methyl-α-ethylstyrene
21758-18-9

4-methyl-α-ethylstyrene

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; oxygen; 2,5-Dimercapto-1,3,4-thiadiazole In acetonitrile at 20 - 80℃; under 760.051 Torr; for 15h; Schlenk technique;62%
propionyl chloride
79-03-8

propionyl chloride

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
Stage #1: propionyl chloride With aluminum (III) chloride In toluene at -5 - 20℃; for 1h;
Stage #2: at 82℃; for 2h;
60.12%
propionyl chloride
79-03-8

propionyl chloride

toluene
108-88-3

toluene

A

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

B

(Z)-1-Chlor-1-(4-methylphenyl)-1-propen
73496-70-5

(Z)-1-Chlor-1-(4-methylphenyl)-1-propen

Conditions
ConditionsYield
iron silicate at 25℃;A 30%
B 60%
para-bromotoluene
106-38-7

para-bromotoluene

propiononitrile
107-12-0

propiononitrile

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane; [nickel(II)dichloride(dimethoxyethane)]; trifluoroacetic acid; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In 1,4-dioxane at 60℃; chemoselective reaction;60%
2-methoxy-1-p-tolylpropan-1-one
1451-87-2

2-methoxy-1-p-tolylpropan-1-one

A

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

B

2-methyl-3-(p-methylphenyl)oxethanol-3

2-methyl-3-(p-methylphenyl)oxethanol-3

Conditions
ConditionsYield
In methanol for 6h; Product distribution; Irradiation; var. other α-, α- and m-, or α- and p-substituted propiophenones with var. type of substituents, substituent effects on the photoreaction;A 44%
B 56%
para-bromotoluene
106-38-7

para-bromotoluene

propionaldehyde
123-38-6

propionaldehyde

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
Stage #1: para-bromotoluene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: propionaldehyde In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #3: With iodine; potassium carbonate In tert-butyl alcohol for 3h; Reflux;
54%
2-nitro-1-p-tolylpropan-1-one
74261-47-5

2-nitro-1-p-tolylpropan-1-one

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Conditions
ConditionsYield
With 1-Benzyl-1,4-dihydronicotinamide In N,N,N,N,N,N-hexamethylphosphoric triamide for 48h; Ambient temperature; Irradiation;45%
With 1-Benzyl-1,4-dihydronicotinamide In N,N,N,N,N,N-hexamethylphosphoric triamide for 48h; Ambient temperature; Irradiation;45%
diethylzinc
557-20-0

diethylzinc

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

A

4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

B

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

C

1-p-tolyl-1-propanol
25574-04-3

1-p-tolyl-1-propanol

Conditions
ConditionsYield
With 2,3,6-trimethyl-beta-cyclodextrin In hexane; toluene for 20h; Product distribution; Ambient temperature; var. of β-cyclodextrin, substituent of PhCHO, poor enantioselectivity;A 39%
B 10%
C 34%
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

1-(p-tolyl)cyclopropan-1-ol
40122-37-0

1-(p-tolyl)cyclopropan-1-ol

acetone
67-64-1

acetone

A

1-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propan-2-one
30764-40-0

1-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propan-2-one

B

1-(4-methylphenyl)prop-2-en-1-one
19832-78-1

1-(4-methylphenyl)prop-2-en-1-one

C

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

D

3-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-1-(p-tolyl)propan-1-one

3-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-1-(p-tolyl)propan-1-one

Conditions
ConditionsYield
With dipotassium peroxodisulfate; silver nitrate; 1-benzenesulfonyl-2,2,2-trifluoro-ethanone O-benzyl-oxime In water at 50℃; for 2h;A n/a
B 17%
C 37%
D n/a
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

1-p-tolylpropan-1-one oxime
54582-25-1

1-p-tolylpropan-1-one oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol Heating;100%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

(R)-1-(4-methylphenyl)-1-propanol
25574-04-3, 73854-03-2, 138809-38-8, 112777-65-8

(R)-1-(4-methylphenyl)-1-propanol

Conditions
ConditionsYield
With magnesium chloride In isopropyl alcohol at 25℃; pH=7; Catalytic behavior;100%
With (2-((2,4-dimethyl-5-phenylimidazo[1,5-b]pyridazin-7-yl)amido)-4-methylpentan-1-ol)(1,5-cyclooctadiene)iridium(I); potassium tert-butylate; hydrogen; acetone In tetrahydrofuran at 20℃; under 15.0015 Torr; for 24h; Autoclave; optical yield given as %ee; enantioselective reaction;98%
With C44H48FeIrNO2P(1+)*C32H12BF24(1-); hydrogen; sodium carbonate In methanol at 20℃; under 7500.75 Torr; for 24h; Autoclave; enantioselective reaction;96%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

(S)-1-(4-methylphenyl)propan-1-ol
25574-04-3, 112777-65-8, 138809-38-8, 73854-03-2

(S)-1-(4-methylphenyl)propan-1-ol

Conditions
ConditionsYield
With triiron dodecarbonyl; C52H58N4P2; hydrogen; potassium hydroxide In methanol at 45℃; under 37503.8 Torr; for 10h; enantioselective reaction;99%
With Mucor racemosus 7924 In various solvent(s) pH=5.0;31%
With ketoreductase P3-G09; NADPH In aq. phosphate buffer; isopropyl alcohol at 30℃; for 24h; pH=7; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;n/a
With bis(triphenylphosphine)carbonyliridium(I) chloride; C70H73N4P3; potassium hydroxide In isopropyl alcohol at 40℃; for 0.5h; Inert atmosphere; enantioselective reaction;95 %Chromat.
With ketoreductase KRED-P3-H12; choline chloride; nicotinamide adenine dinucleotide phosphate; magnesium sulfate; glycerol In aq. phosphate buffer; isopropyl alcohol at 30℃; for 24h; pH=7; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

trimethyl orthoformate
149-73-5

trimethyl orthoformate

methyl 2-(4-methylphenyl)propanoate
79443-97-3

methyl 2-(4-methylphenyl)propanoate

Conditions
ConditionsYield
With sulfuric acid; 3-[4-(diacetoxyiodo)phenoxy]-1-propyl-N,N,N-trimethylammonium 4-methylbenzenesulfonate at 60℃; for 3h; Inert atmosphere;98%
With sulfuric acid; N-trifluoromethanesulfonyl-4-(diacetoxyiodo)pyrazole at 60℃; for 2h;96%
With sulfuric acid; 1-(diacetoxyiodo)-4-methylbenzene at 60℃; for 2h;92%
morpholine
110-91-8

morpholine

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

(E)-3-morpholino-1-(p-tolyl)prop-2-en-1-one
71035-24-0

(E)-3-morpholino-1-(p-tolyl)prop-2-en-1-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; chlorobenzene; trimethylphosphane In tetrahydrofuran; 1,4-dioxane at 100℃; for 40h; Inert atmosphere;98%
para-chlorotoluene
106-43-4

para-chlorotoluene

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

1,2-bis(4-methylphenyl)propan-1-one
89037-30-9

1,2-bis(4-methylphenyl)propan-1-one

Conditions
ConditionsYield
With C40H44ClN3Pd; sodium t-butanolate In toluene at 80℃; for 3h; Inert atmosphere;97%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

2-bromo-4'-methylpropiophenone
92821-88-0, 1451-82-7

2-bromo-4'-methylpropiophenone

Conditions
ConditionsYield
With aluminum (III) chloride; bromine In diethyl ether at 0℃;96%
With bromine In hexane; water; acetic acid; ethyl acetate95%
With bromine; acetic acid at 30℃;89%
1,3-DIOXOLANE
646-06-0

1,3-DIOXOLANE

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

piperidine hydrochloride
6091-44-7

piperidine hydrochloride

Tolperisone hydrochloride

Tolperisone hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 90℃; for 8h;96%
di-p-tolylcarbodiimide
726-42-1

di-p-tolylcarbodiimide

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

4,4'-dimethylbenzanilide
6876-66-0

4,4'-dimethylbenzanilide

Conditions
ConditionsYield
With [{HMn(CO)4}3] In 1,4-dioxane at 135℃; for 24h; Sealed tube; Inert atmosphere;96%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

Conditions
ConditionsYield
With Co4HP2Mo15V3O62; N-(4-sulfonic acid)butyl triethylammonium tetrafluoroborate; dihydrogen peroxide at 50℃; for 4h; Green chemistry;96%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

chlorobenzene
108-90-7

chlorobenzene

rac-1-(4-methylphenyl)-2-phenylpropan-1-one
14161-82-1

rac-1-(4-methylphenyl)-2-phenylpropan-1-one

Conditions
ConditionsYield
With C40H44ClN3Pd; sodium t-butanolate In toluene at 80℃; for 3h; Inert atmosphere;96%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

2-bromo-1-(4-methylphenyl)ethylene
60655-80-3

2-bromo-1-(4-methylphenyl)ethylene

3-methyl-2,5-di-p-tolylfuran

3-methyl-2,5-di-p-tolylfuran

Conditions
ConditionsYield
With cobalt(II) chloride hexahydrate; [bis(acetoxy)iodo]benzene; N-ethyl-N,N-diisopropylamine; 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide In dimethyl sulfoxide; acetonitrile at 80℃; for 7h; Reagent/catalyst; Solvent;95.8%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

formic acid 1-methyl-2-oxo-2-p-tolyl-ethyl ester

formic acid 1-methyl-2-oxo-2-p-tolyl-ethyl ester

Conditions
ConditionsYield
With (trifluoromethyl)trimethylsilane; copper(ll) bromide for 24h;95%
Stage #1: 4'-methylpropiophenone; N,N-dimethyl-formamide With trifluorormethanesulfonic acid; thallium(III) acetate at 60℃; for 0.333333h;
Stage #2: With water for 0.166667h; Further stages.;
91%
iodomethane-d3
865-50-9

iodomethane-d3

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

4'-methyl-d3-isobutyrophenone
1037431-15-4

4'-methyl-d3-isobutyrophenone

Conditions
ConditionsYield
Stage #1: 4'-methylpropiophenone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h;
Stage #2: iodomethane-d3 In tetrahydrofuran at -78 - 20℃;
95%
acetamide
60-35-5

acetamide

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

2,5-dimethyl-4-(p-tolyl)oxazole

2,5-dimethyl-4-(p-tolyl)oxazole

Conditions
ConditionsYield
Stage #1: 4'-methylpropiophenone With hydroxy(phenyl)-λ3-iodanyl 2,4-dinitrobenzenesulfonate for 0.0111111h; microwave irradiation;
Stage #2: acetamide for 0.0333333h; microwave irradiation;
94%
Stage #1: 4'-methylpropiophenone With hydroxy(phenyl)-λ3-iodanyl 2,4-dinitrobenzenesulfonate In acetonitrile Heating;
Stage #2: acetamide In acetonitrile Heating;
75%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

α-chloro-4-methyl propiophenone
69673-92-3

α-chloro-4-methyl propiophenone

Conditions
ConditionsYield
With Aluminum(III) chloride hexahydrate; urea-hydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 60℃; for 6h;94%
With N-chloro-succinimide; urea-hydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 60℃;70%
morpholine
110-91-8

morpholine

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

2-morpholino-1-(4-(methyl)phenyl)propan-1-one
1152957-31-7

2-morpholino-1-(4-(methyl)phenyl)propan-1-one

Conditions
ConditionsYield
Stage #1: 4'-methylpropiophenone With 2,6-bis[(4,4-dimethyl)-2-oxazolin-2-yl]pyridine copper bromide In dimethyl sulfoxide at 20℃; for 0.166667h; Green chemistry;
Stage #2: morpholine In dimethyl sulfoxide at 20℃; for 10h; Green chemistry;
94%
With sodium percarbonate; ammonium iodide In acetonitrile at 50℃; for 18h;94%
With 2,6-bis[(4,4-dimethyl)-2-oxazolin-2-yl]pyridine copper bromide In dimethyl sulfoxide at 20℃; for 15h;94%
piperidine
110-89-4

piperidine

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

2-piperidin-1-(4-methylphenyl)propan-1-one
25872-67-7

2-piperidin-1-(4-methylphenyl)propan-1-one

Conditions
ConditionsYield
Stage #1: 4'-methylpropiophenone With 2,6-bis[(4,4-dimethyl)-2-oxazolin-2-yl]pyridine copper bromide In dimethyl sulfoxide at 20℃; for 0.166667h; Green chemistry;
Stage #2: piperidine In dimethyl sulfoxide at 20℃; for 10h; Green chemistry;
94%
With ammonium iodide In acetonitrile at 20℃; Electrolysis;52%
methanol
67-56-1

methanol

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

4'-methylisobutyrophenone
50390-51-7

4'-methylisobutyrophenone

Conditions
ConditionsYield
With C21H25ClIrN2O2(1+)*Cl(1-); potassium carbonate at 120℃; for 12h; Schlenk technique; Inert atmosphere;94%
With C34H27IrN2P(1+)*C32H12BF24(1-); caesium carbonate at 65℃; for 24h; Inert atmosphere;93%
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; potassium carbonate at 80℃; for 24h;92%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

1-oxo-1-p-tolylpropan-2-yl 4-methylbenzoate

1-oxo-1-p-tolylpropan-2-yl 4-methylbenzoate

Conditions
ConditionsYield
With potassiumhexacyanoferrate(II) trihydrate; 2,6-bis[(4,4-dimethyl)-2-oxazolin-2-yl]pyridine copper bromide; oxygen In N,N-dimethyl-formamide at 110℃; for 8h; Green chemistry;94%
With tert.-butylhydroperoxide; iodine; sodium carbonate In water; acetonitrile at 70℃; for 24h;76%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

1-(4-bromophenyl)-2,2-dihydroxyethanone
80352-42-7

1-(4-bromophenyl)-2,2-dihydroxyethanone

3-(4-methylphenyl)-6-(4-bromophenyl)-4-methylpyridazine

3-(4-methylphenyl)-6-(4-bromophenyl)-4-methylpyridazine

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; hydrazine hydrate In water at 25℃; Green chemistry; regioselective reaction;94%
NH-pyrazole
288-13-1

NH-pyrazole

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

2-methyl-3-(1H-pyrazol-1-yl)-1-(p-tolyl)propan-1-one

2-methyl-3-(1H-pyrazol-1-yl)-1-(p-tolyl)propan-1-one

Conditions
ConditionsYield
With Selectfluor at 120℃; Mannich Aminomethylation; Sealed tube;94%
2,2,6,6-tetramethylheptane-3,5-dione
1118-71-4

2,2,6,6-tetramethylheptane-3,5-dione

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

6,6-dimethyl-4-pivaloyl-1-(p-tolyl)heptane-1,5-dione

6,6-dimethyl-4-pivaloyl-1-(p-tolyl)heptane-1,5-dione

Conditions
ConditionsYield
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In 1,2-dichloro-benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique;94%
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

1-oxo-1-p-tolylpropan-2-yl acetate
69673-81-0

1-oxo-1-p-tolylpropan-2-yl acetate

Conditions
ConditionsYield
Stage #1: N,N-dimethyl acetamide; 4'-methylpropiophenone With trifluorormethanesulfonic acid; thallium(III) acetate at 60℃; for 0.333333h;
Stage #2: With water for 0.166667h; Further stages.;
93%
4'-methylpropiophenone
5337-93-9

4'-methylpropiophenone

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

4-methyl-α-ethylstyrene
21758-18-9

4-methyl-α-ethylstyrene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Wittig Olefination; Inert atmosphere;
Stage #2: 4'-methylpropiophenone In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
93%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0 - 5℃; for 3h;
Stage #2: 4'-methylpropiophenone In tetrahydrofuran for 16h; Heating;
10%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane Wittig reaction; Inert atmosphere;
Stage #2: 4'-methylpropiophenone In tetrahydrofuran; hexane Wittig reaction; Inert atmosphere;

5337-93-9Relevant articles and documents

α-Hydroxylation of α,α-Disubstituted N-tert-Butanesulfinyl Ketimines with Molecular Oxygen: Stereoselective Synthesis of α-Tertiary Hydroxyimines

Liu, Hui,Lu, Chong-Dao,Yao, Yun,Yisimayili, Nuermaimaiti

supporting information, (2022/01/20)

α-Tertiary hydroxyimines were stereoselectively synthesized from enantioenriched N-tert-butanesulfinyl ketimines using potassium tert-butoxide, molecular oxygen, and trimethyl phosphite. The stereoselective hydroxylation of acyclic ketimines bearing two sterically similar α-substituents was achieved by controlling the geometry of the metalloenamine intermediates and the facial selectivity of hydroxylation. The synthetic utility of the resulting α-tertiary hydroxyimines was demonstrated through the successful diastereoselective synthesis of highly substituted β-amino alcohols.

Cobalt-Catalyzed Reductive C-O Bond Cleavage of Lignin β-O-4 Ketone Models via in Situ Generation of the Cobalt-Boryl Species

Gao, Kecheng,Xu, Man,Cai, Cheng,Ding, Yanghao,Chen, Jianhui,Liu, Bosheng,Xia, Yuanzhi

supporting information, p. 6055 - 6060 (2020/08/12)

An efficient and mild method for reductive C-O bond cleavage of lignin β-O-4 ketone models was developed to afford the corresponding ketones and phenols with PDI-CoCl2 as the precatalyst and diboron reagent as the reductant. The synthetic utility of the methodology was demonstrated by depolymerization of a polymeric model and gram-scale transformation. Mechanistic studies suggested that this transformation involves steps of carbonyl insertion, 1,2-Brook type rearrangement, β-oxygen elimination, and rate-limiting regeneration of the catalytic active Co-B species.

Metal-Organic Framework Based on Heptanuclear Cu-O Clusters and Its Application as a Recyclable Photocatalyst for Stepwise Selective Catalysis

Zhou, Jie,Huang-Fu, Xu,Huang, Yang-Ying,Cao, Chu-Ning,Han, Jie,Zhao, Xiao-Li,Chen, Xu-Dong

, p. 254 - 263 (2019/12/04)

Visible-light driven photoreactions using metal-organic frameworks (MOFs) as catalysts are promising with regard to their environmental friendly features such as the use of renewable and sustainable energy of visible light and potential catalyst recyclability. To develop potential heterogeneous photocatalysts, a family of three copper(II) coordination polymers bearing different Cu-O assemblies have been synthesized with the ligand 4,4-disulfo-[1,1-biphenyl]-2,2-dicarboxylate acid (H4DSDC), namely, {[Cu7(DSDC)2(OH)6(H2O)10]·xH2O}n (1), {[Cu4(DSDC)(4,4-bpy)2(OH)4]·2H2O}n (2), and {Cu2(DSDC)(phen)2(H2O)2}n (3) (4,4-bpy = 4,4-bipyridine and phen = 1,10-phenanthroline). Complex 1 represents a metal-organic framework featuring a NbO type topology constructed from the infinite linkage of heptanuclear [Cu7(μ3-OH)6(H2O)10]8+ clusters by deprotonated DSDC4- ligands, comprising one-dimensional hexagonal channels of a diameter around 11 ? that are filled with water molecules. The infinite waving {[Cu2(OH)2]2+}n ladderlike chains in complex 2 are bridged by DSDC4- and 4,4-bpy ligands into a three-dimensional framework. A two-dimensional layered structure is formed in complex 3 due to the existence of terminal phenanthroline ligands. All of the coordination polymers 1-3 are able to catalyze the visible-light driven oxidation of alcohols at mild conditions using hydrogen peroxide as an oxidant, in which complex 1 demonstrates satisfactory efficiency. Significantly for this photoreaction catalyzed by 1, the extent of oxidation over aryl primary alcohols is fully controllable with time-resolved product selectivity, giving either corresponding aldehydes or carboxylate acids in good yields. It is also remarkable that the photocatalyst could be recovered almost quantitatively on completion of the catalytic cycle without any structure change, and could be recycled for catalytic use for at least five cycles with constant efficiency. This photocatalyst with time-resolved selectivity for different products may provide new insight into the design and development of novel catalytic systems.

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