Conditions | Yield |
---|---|
With HOF* CH3CN In chloroform; water | 100% |
With silica gel; magnesium monoperoxyphthalate hexahydrate In dichloromethane for 1.16667h; Heating; | 100% |
With sodium tungstate (VI) dihydrate; dihydrogen peroxide In methanol; water at 40℃; | 100% |
(3aS,4aS,6S,7S,7aS,7bS)-7-((Z)-6-Chloro-hex-2-enyl)-2,2-dimethyl-6-(toluene-4-sulfonyl)-hexahydro-cyclopenta[4,5]furo[2,3-d][1,3]dioxole
1,1-dibromomethane
(3aS,4aS,7S,7aS,7bS)-7-((Z)-6-Chloro-hex-2-enyl)-2,2-dimethyl-6-methylene-hexahydro-cyclopenta[4,5]furo[2,3-d][1,3]dioxole
B
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
Stage #1: (3aS,4aS,6S,7S,7aS,7bS)-7-((Z)-6-Chloro-hex-2-enyl)-2,2-dimethyl-6-(toluene-4-sulfonyl)-hexahydro-cyclopenta[4,5]furo[2,3-d][1,3]dioxole With n-butyllithium In tetrahydrofuran; hexane at -100 - -73℃; Stage #2: 1,1-dibromomethane In tetrahydrofuran; hexane at -99 - -63℃; | A 96.4% B n/a |
Conditions | Yield |
---|---|
With sodium acetate In ethanol for 15h; Heating; | 95% |
Conditions | Yield |
---|---|
With copper(l) iodide In dimethyl sulfoxide for 24h; Heating; | 95% |
With copper(l) iodide; sodium L-prolinate In dimethyl sulfoxide at 80℃; for 24h; | 93% |
With potassium phosphate; copper(l) iodide; (2S,4R)-4-hydroxy-N-(2-methylnaphthalen-1-yl)pyrrolidine-2-carboxamide In dimethyl sulfoxide at 120℃; Sealed tube; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 0.333333h; | 94% |
4-methylphenyl methylsulfide
A
Methyl p-tolyl sulfoxide
B
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In acetonitrile at -15℃; for 11h; Oxidation; | A 93% B 2 % Spectr. |
With dihydrogen peroxide; titanium binaphthyl-bridged Schiff base at 4℃; for 6h; Product distribution; Further Variations:; Temperatures; | A 92% B 8% |
With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; N-(p-nitrobenzylidene)benzenesulfonamide; potassium carbonate; potassium hydrogencarbonate In dichloromethane at 25℃; for 0.5h; Product distribution; other sulfides; var. equiv of oxone; var. time; | A 91% B 5% |
n-butyllithium
(3aS,4aS,6S,7S,7aS,7bS)-7-((Z)-6-Chloro-hex-2-enyl)-2,2-dimethyl-6-(toluene-4-sulfonyl)-hexahydro-cyclopenta[4,5]furo[2,3-d][1,3]dioxole
1,1-dibromomethane
(3aS,4aS,7S,7aS,7bS)-7-((Z)-6-Chloro-hex-2-enyl)-2,2-dimethyl-6-methylene-hexahydro-cyclopenta[4,5]furo[2,3-d][1,3]dioxole
C
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
Stage #1: (3aS,4aS,6S,7S,7aS,7bS)-7-((Z)-6-Chloro-hex-2-enyl)-2,2-dimethyl-6-(toluene-4-sulfonyl)-hexahydro-cyclopenta[4,5]furo[2,3-d][1,3]dioxole With n-butyllithium In tetrahydrofuran; hexane at -68 - -48℃; Stage #2: n-butyllithium; 1,1-dibromomethane In tetrahydrofuran; hexane at -68 - -55℃; | A 1.1% B 91.3% C 3.6% |
Conditions | Yield |
---|---|
With potassium superoxide; 2-Nitrobenzenesulfonyl chloride In acetonitrile at -30℃; for 6h; | 90% |
With 3-chloro-benzenecarboperoxoic acid | 75% |
With iodoxybenzene; bis(acetylacetonate)oxovanadium In benzene Heating; | 70% |
4-methylphenyl methylsulfide
A
(R)-methyl p-tolyl sulfoxide
B
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; Cumene hydroperoxide; C22H30O12 In dichloromethane; water at -20℃; for 1h; Kinetics; Reagent/catalyst; Concentration; Time; Solvent; Inert atmosphere; enantioselective reaction; | A 90% B n/a |
Stage #1: 4-methylphenyl methylsulfide With bis(acetylacetonate)oxovanadium; (R)-2-((1-hydroxy-3,3-dimethylbutan-2-ylimino)methyl)-4,6-diiodophenol In chloroform at 20℃; for 0.5h; Stage #2: With dihydrogen peroxide In chloroform at 0℃; for 48h; | A 82% B n/a |
With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; 1-(5-methylfuran-2-yl)hept-1-yl hydroperoxide In dichloromethane at 20℃; for 22h; | A 61% B 30% |
Stage #1: 4-methylphenyl methylsulfide With titanium(IV) isopropylate; C51H54N2O4 In methanol; dichloromethane; water at 20℃; for 0.333333h; Inert atmosphere; Stage #2: With dihydrogen peroxide In methanol; dichloromethane; water at 0℃; for 1.5h; Inert atmosphere; enantioselective reaction; | A n/a B n/a |
Conditions | Yield |
---|---|
With phosphorus pentoxide at 170℃; for 0.5h; Large scale; | 90% |
di-tert-butyl peroxide
sodium 4-methylbenzenesulfinate
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
In water at 80℃; for 12h; Sealed tube; | 89% |
With water at 110℃; for 12h; Sealed tube; Green chemistry; | 89% |
4-methylphenyl methylsulfide
A
(S)-methyl p-tolyl sulfoxide
B
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
With dihydrogen peroxide; chiral Fe(III) salan complex at 20℃; for 3h; | A 88% B 9 % Spectr. |
With phosphate buffer; dihydrogen peroxide; chiral Al(salalen) In methanol at 20℃; for 24h; | A 82% B 9 % Spectr. |
With tert.-butylhydroperoxide In tetrachloromethane; water at 20℃; for 20h; optical yield given as %ee; enantioselective reaction; | A 62% B n/a |
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate) In water at 120℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere; Green chemistry; | 88% |
Conditions | Yield |
---|---|
With phosphorus pentoxide at 130℃; for 1h; Temperature; Large scale; | 88% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium Tetrafluoroborate In water at 25℃; for 24h; | 87% |
In water; N,N-dimethyl-formamide for 0.025h; Ambient temperature; Irradiation; | 85% |
In ethanol | 85% |
p-toluenesulfonyl fluoride
methylmagnesium chloride
A
bis(4-methylphenylsulfonyl)methane
B
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
In tetrahydrofuran for 19h; Ambient temperature; | A 8% B 87% |
Conditions | Yield |
---|---|
With 2-Methylcyclopentanone; benzylamine In acetic acid for 1.5h; Heating; | 86% |
With potassium hydroxide |
Conditions | Yield |
---|---|
In tetrahydrofuran for 18h; Ambient temperature; | 86% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; (Ra,S,S,Ra)-Al(salalen) In phosphate buffer at -10℃; pH=7.4; | A n/a B 86% |
methylene chloride
sodium 4-methylbenzenesulfinate
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
at 20 - 90℃; under 3750.38 - 19502 Torr; Temperature; Concentration; Autoclave; | 85.3% |
methyllithium
1-<(4-Methylphenylsulfonyloxy)methyl>bicyclo<3.3.1>nonan-2-on
A
1-(Hydroxymethyl)bicyclo<3.3.1>nonan-2-on
B
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
In diethyl ether; hexane for 3h; Heating; | A 47% B 85% |
Conditions | Yield |
---|---|
Stage #1: methyl p-toluene sulfinate With sodium hydroxide In water at 80℃; for 3h; Stage #2: methylene chloride In water at 90℃; under 3000.3 Torr; Temperature; Autoclave; | 83.54% |
Conditions | Yield |
---|---|
With copper(l) iodide In dimethyl sulfoxide for 36h; Heating; | 83% |
sodium methansulfinate
bis(4-methylphenyl)iodonium trifluoromethanesulfonate
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
With PEG-400 at 50℃; for 0.5h; Microwave irradiation; Sealed tube; | 83% |
4-bromoohenyl methyl sulfone
methyl p-toluene sulfonate
Methyl p-tolyl sulfone
Conditions | Yield |
---|---|
With nickel(II) iodide; 4,4'-dimethyl-2,2'-bipyridines; tetra-(n-butyl)ammonium iodide; magnesium chloride; zinc In N,N-dimethyl acetamide at 20℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; | 83% |
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium dithionite; tetrabutylammomium bromide In dimethyl sulfoxide at 120℃; for 15h; | 82% |
The Methyl p-tolyl sulfone, with the CAS registry number 3185-99-7, is also known as p-(Methylsulphonyl)toluene. It belongs to the product categories of Boron, Nitrile, Thio & TM-Cpds. Its EINECS registry number is 221-682-8. This chemical's molecular formula is C8H10O2S and molecular weight is 170.23. What's more, both its IUPAC name and systematic name are the same which is called 1-Methyl-4-methylsulfonylbenzene.
Physical properties about Methyl p-tolyl sulfone are: (1)ACD/LogP: 0.96; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.96; (4)ACD/LogD (pH 7.4): 0.96; (5)ACD/BCF (pH 5.5): 3.16; (6)ACD/BCF (pH 7.4): 3.16; (7)ACD/KOC (pH 5.5): 79.3; (8)ACD/KOC (pH 7.4): 79.3; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 42.52 Å2; (13)Index of Refraction: 1.519; (14)Molar Refractivity: 44.81 cm3; (15)Molar Volume: 147.4 cm3; (16)Surface Tension: 36.1 dyne/cm; (17)Density: 1.154 g/cm3; (18)Flash Point: 173.4 °C; (19)Enthalpy of Vaporization: 53.06 kJ/mol; (20)Boiling Point: 311.7 °C at 760 mmHg; (21)Vapour Pressure: 0.00102 mmHg at 25 °C.
Preparation of Methyl p-tolyl sulfone: this chemical can be prepared by 1-Methyl-4-methylsulfanyl-benzene. The reaction occurs with reagent acetonitrile and other condition of heating for 5 hours. The yield is 91 %.
Uses of Methyl p-tolyl sulfone: (1) It is used as medicine, dye, veterinary medicine and synthetic intermediates; (2) it is used to produce other chemicals. For example, it can produce1-Bromomethyl-4-methanesulfonyl-benzene. This reaction needs reagents N-bromosuccinimide and AIBN at temperature of 60-65 °C. The reaction time is 1 hour. The yield is 77 %.
When you are dealing with this chemical, you should be very careful. This chemical may catch fire in contact with air, only need brief contact with an ignition source and have a very low flash point or evolve highly flammable gases in contact with water. It is irritating to respiratory system and skin. It has serious damage to eyes. Therefore, you should wear suitable protective clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: O=S(=O)(c1ccc(cc1)C)C
(2) InChI: InChI=1S/C8H10O2S/c1-7-3-5-8(6-4-7)11(2,9)10/h3-6H,1-2H3
(3) InChIKey: YYDNBUBMBZRNQQ-UHFFFAOYSA-N
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