Conditions | Yield |
---|---|
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; water; phenylzinc(II) bromide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 100% |
Stage #1: p-toluenesulfonyl chloride With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 22℃; Stage #2: With trifluoroacetic acid In dichloromethane Further stages.; | 95% |
With pyridine; dmap In dichloromethane | 82% |
Conditions | Yield |
---|---|
With dinitrogen tetraoxide In tetrachloromethane; diethyl ether for 2.5h; Ambient temperature; | 100% |
With dihydrogen peroxide; trichlorophosphate In water at 80℃; for 1.16667h; Micellar solution; | 95% |
With HOF* CH3CN In dichloromethane at 0℃; | 90% |
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetonitrile at 20℃; | 87% |
Multi-step reaction with 2 steps 1: pyridine / acetonitrile / Heating 2: hydrogenchloride; water / 40 °C View Scheme |
1-(p-methylbenzenesulfonoyloxy)-2(1H)-quinolone
A
toluene-4-sulfonic acid
B
1-hydroxycarbostyril
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran for 2h; Product distribution; Ambient temperature; | A n/a B 98% |
triethylammonium toluene-p-sulfonate
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
With sulfuric acid In water pH=3; | 97.5% |
A
C16H10O3S
B
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
In chloroform-d1 for 0.233333h; Photolysis; Inert atmosphere; | A n/a B 97% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; trichlorophosphate In water at 80℃; for 1h; Micellar solution; | 94% |
Conditions | Yield |
---|---|
With sulfur trioxide at 35 - 65℃; Temperature; Inert atmosphere; | 93.3% |
With sodium hydrogensulfite; pyridinium chlorochromate In neat (no solvent) at 100℃; under 1500.15 Torr; for 0.0666667h; Reagent/catalyst; Microwave irradiation; | 93% |
With 1,3-disulfonic acid imidazolonium chloride In water at 50℃; for 0.05h; Green chemistry; regioselective reaction; | 72% |
toluene-4-sulfonic acid 2,2,2-trifluoro-1-p-tolyl-ethyl ester
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
With trifluoroacetic acid In water at 20℃; for 2h; | 91% |
phenethylamine
p-toluenesulfonyl chloride
A
4-methyl-N-(2-phenylethyl)benzenesulfonamide
B
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 2h; Product distribution; Mechanism; further amines; | A 90% B 10% |
With n-butyllithium 1) THF, hexane, -10 deg C, 15 min, 2) THF, hexane, -50 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; |
phenylmethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethyl-6-(trifluoroacetylamino)-(6β,8aβ)-2(1H)-isoquinolinecarboxylate
B
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
In ethanol; di-isopropyl ether; palladium | A n/a B 90% |
1-(p-methylbenzenesulfonoyloxy)-2(1H)-quinolone
A
2-quinolone
B
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
In methanol; water Quantum yield; UV-irradiation; Photolysis; | A n/a B 90% |
Toluene-4-sulfonic acid 2-methyl-1,2-diphenyl-propyl ester
A
2-methyl-1,1-diphenylpropene
B
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
at 115℃; Product distribution; Rate constant; Thermodynamic data; Ea(excit.), ΔS(excit.); | A 85% B n/a |
N'-2-butanylidene-4-methylbenzenesulfonohydrazine
A
toluene-4-sulfonic acid
B
butanone
Conditions | Yield |
---|---|
With molecular sieve; dihydrogen peroxide In methanol for 4h; Mechanism; Heating; other solvent; tosylhydrazones of other ketones; | A n/a B 84% |
A
Mucochloric acid
B
3,4-dichloro-5-[(4-methyl phenyl)sulfonyl]-2(5H)-furanone
C
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetic acid at 20℃; for 96h; | A n/a B 83% C n/a |
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; Aminoiminomethanesulfinic acid In dimethyl sulfoxide at 100℃; for 14h; | 80% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; Aminoiminomethanesulfinic acid In dimethyl sulfoxide at 100℃; for 14h; Reagent/catalyst; Solvent; Green chemistry; | 78% |
Conditions | Yield |
---|---|
With bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 2h; Heating; | 78% |
Conditions | Yield |
---|---|
With 18O-labeled water In dimethyl sulfoxide at 100℃; for 14h; Reagent/catalyst; | 75% |
With hydrogenchloride; oxygen In d(4)-methanol at 20℃; for 0.166667h; |
1-tosyloxy-4-phenyl-2-butanone
A
4-Methylbiphenyl
B
4-Phenyl-2-butanone
C
1,4-diphenyl-2-butanone
D
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
In benzene Irradiation; | A 13% B 7% C 10% D 74% |
Toluene-4-sulfonic acid 2,2-dimethyl-3-oxo-1,3-diphenyl-propyl ester
A
3-methyl-1,2-diphenylbut-2-en-1-one
B
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
at 130℃; Product distribution; Rate constant; Thermodynamic data; Ea(excit.), ΔS(excit.); | A 74% B n/a |
Conditions | Yield |
---|---|
With hydroxy(tosyloxy)iodobenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 5h; Ambient temperature; | A 32% B 71% |
(cyclopent-2-eneyl)acetic acid
A
3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
B
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
With hydroxy(tosyloxy)iodobenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 4h; Ambient temperature; | A 56% B 70% |
triphenylmethanethiol
toluene-p-sulfonyl bromide
A
triphenylmethyl alcohol
B
toluene-4-sulfonic acid
C
Toluene-4-thiosulfonic acid S-trityl ester
Conditions | Yield |
---|---|
With triethylamine In tetrachloromethane at 0℃; for 0.5h; Yields of byproduct given; | A n/a B n/a C 70% |
N,N'-bis(p-toluenesulfonyl)hydroxylamine
A
bis(4-methylphenylsulfonyl)amino 4-methylbenzenesulfonate
B
toluene-4-sulfonic acid
C
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With air In chloroform for 12h; Product distribution; Mechanism; Ambient temperature; various reaction conditions; | A 20% B 70% C 5% |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; water for 0.5h; | 69% |
Stage #1: sodium tosylate In tert-butyl methyl ether; water for 0.166667h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water for 0.333333h; |
[hydroxy(tosyloxy)iodo]benzene
5-norbornene-endo-2-carboxylic acid
Toluene-4-sulfonic acid (1S,3S,6S,7R)-4-oxo-5-oxa-tricyclo[4.3.0.03,7]non-9-yl ester
B
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
In dichloromethane at 0℃; | A 28% B 60% |
2,2-Dimethyl-3-phenyl-3-(toluene-4-sulfonyloxy)-propionic acid ethyl ester
A
ethyl isopropylidenephenylacetic carboxylate
B
ethyl 2-methylene-3-phenylbutanoate
C
toluene-4-sulfonic acid
D
Ethyl 1-methyl-2-phenylcyclopropane-1-carboxylate
Conditions | Yield |
---|---|
at 145 - 160℃; Product distribution; Kinetics; Thermodynamic data; Ea(excit.), ΔS(excit.); | A 58% B 6% C n/a D 5% |
N,N'-ditosylhydrazine
A
bis(4-methylphenyl)disulfone
B
toluene-p-sulfonyl bromide
C
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
With bromine In water; acetonitrile at 20℃; | A 10% B 57% C 20% |
3-methoxy-1-methyl-1,2,5,6-tetrahydropyridine
toluene-4-sulfonic acid
3-methoxy-1-methyl-1,2,5,6-tetrahydropyridinium toluene-p-sulphonate
Conditions | Yield |
---|---|
In acetone for 0.25h; educt toluene-p-sulphonic acid: anhydrous; | 100% |
methyl (+/-)-trans-(2,3)-epoxy butanoate
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
100% |
Trimethyl orthoacetate
toluene-4-sulfonic acid
methyl p-toluene sulfonate
Conditions | Yield |
---|---|
at 20℃; for 0.5h; | 100% |
In dichloromethane for 0.5h; Ambient temperature; | 96% |
Conditions | Yield |
---|---|
for 24h; Heating; | 100% |
L-valine
2-methyl-propan-1-ol
toluene-4-sulfonic acid
(S)-1-isobutoxy-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
In water; toluene for 24h; Reflux; Dean-Stark; | 100% |
In benzene Heating; | 84% |
In benzene Heating; |
[bis(acetoxy)iodo]benzene
toluene-4-sulfonic acid
[hydroxy(tosyloxy)iodo]benzene
Conditions | Yield |
---|---|
In acetonitrile | 100% |
for 0.166667h; | 97% |
In acetonitrile at 20℃; | 94% |
(S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoic acid 2-trimethylsilanyl-ethyl ester
toluene-4-sulfonic acid
Nε-(Benzyloxycarbonyl)-L-lysine 2-(Trimethylsilyl)ethyl Ester p-Toluenesulfonate
Conditions | Yield |
---|---|
In benzene for 1h; Heating; | 100% |
toluene-4-sulfonic acid
(S)-2-tert-Butoxycarbonylamino-propionic acid 6-((S)-2-tert-butoxycarbonylamino-propionyloxy)-hexa-2,4-diynyl ester
(S)-2-Amino-propionic acid 6-((S)-2-amino-propionyloxy)-hexa-2,4-diynyl ester; compound with toluene-4-sulfonic acid
Conditions | Yield |
---|---|
With acetic acid at 50℃; | 100% |
toluene-4-sulfonic acid
Z-L-Leu-L-Lys(Boc)-L-Lys(Boc)-OPh
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal for 1.33333h; | 100% |
toluene-4-sulfonic acid
Z-L-Ser(tBu)-L-Lys(Boc)-L-Leu-L-Lys(Boc)-L-Lys(Boc)-OPh
H-L-Ser(tBu)-L-Lys(Boc)-L-Leu-L-Lys(Boc)-L-Lys(Boc)-OPh*TosOH
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 1h; | 100% |
toluene-4-sulfonic acid
Z-L-Glu(OtBu)-L-Lys(Boc)-L-Asn-L-Pro-L-Leu-L-Pro-L-Ser(tBu)-OPh
H-L-Glu(OtBu)-L-Lys(Boc)-L-Asn-L-Pro-L-Leu-L-Pro-L-Ser(tBu)-OPh*TosOH
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 4h; | 100% |
toluene-4-sulfonic acid
Z-L-Leu-L-Pro-L-Ser(tBu)-OPh
H-L-Leu-L-Pro-L-Ser(tBu)-OPh*TosOH
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 1.5h; | 100% |
toluene-4-sulfonic acid
Z-L-Thr(tBu)-L-Gln-L-Glu(OtBu)-L-Lys(Boc)-OPh
H-L-Thr(tBu)-L-Gln-L-Glu(OtBu)-L-Lys(Boc)-OPh*TosOH
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 1h; | 100% |
toluene-4-sulfonic acid
α-<2-(trimethylsilyl)ethyl> γ-n-hexadecyl N-(tert-butyloxycarbonyl)-L-glutamate
α-<2-(trimethylsilyl)ethyl> γ-n-hexadecyl L-glutamate tosylate
Conditions | Yield |
---|---|
In benzene for 1h; Heating; | 100% |
Conditions | Yield |
---|---|
100% |
toluene-4-sulfonic acid
nonafluorobutyliodine(III) bis(trifluoroacetate)
perfluorobutane
Conditions | Yield |
---|---|
In acetonitrile at 0 - 20℃; | 100% |
In acetonitrile Ambient temperature; | 91% |
In acetonitrile at -20 - 20℃; for 1h; | 91% |
L-leucine
toluene-4-sulfonic acid
benzyl alcohol
L-leucine benzyl ester p-toluenesulfonate
Conditions | Yield |
---|---|
In cyclohexane; water for 4h; Dean-Stark; Reflux; | 100% |
In toluene for 20h; Reflux; | 85% |
In toluene for 4h; Reflux; Inert atmosphere; | 82% |
S-tert-Butyl-N-acetyl-L-cysteine hydrochloride
toluene-4-sulfonic acid
benzyl alcohol
p-Toluenesulfonate of S-tert-Butyl-L-cysteine Benzyl Ester
Conditions | Yield |
---|---|
In chloroform for 6h; Heating; | 100% |
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 8h; | 100% |
L-alanin
toluene-4-sulfonic acid
benzyl alcohol
L-alanine benzyl ester p-toluenesulfonate
Conditions | Yield |
---|---|
In benzene for 10h; Reflux; Inert atmosphere; | 100% |
at 50 - 62℃; under 15.0015 Torr; for 5.5h; | 98.6% |
In cyclohexane; water for 4h; Dean-Stark; Reflux; | 92% |
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
In diethyl ether at 35℃; for 2h; | 100% |
Conditions | Yield |
---|---|
In benzene at 90℃; for 16h; | 100% |
In benzene for 12h; Esterification; Heating; | 95% |
Conditions | Yield |
---|---|
In toluene for 5h; Inert atmosphere; Heating; | 100% |
In benzene for 24h; Reflux; | 96% |
In benzene Esterification; |
Conditions | Yield |
---|---|
In toluene at 140℃; for 24h; Dean-Stark; Schlenk technique; Inert atmosphere; | 100% |
In benzene for 42h; Heating; |
toluene-4-sulfonic acid
2-(2,4,5,8-tetrahydroxy-7-oxa-2-azabicyclo[3.2.1]oct-3-yl)-2-[(O-t-butylcarbonyl)(N-benzyloxycarbonyl)tyrosylamino]acetic acid n-butyl ester
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol for 2h; | 100% |
toluene-4-sulfonic acid
{tert-butoxycarbonylmethyl-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-amino}-acetic acid tert-butyl ester
Conditions | Yield |
---|---|
In dichloromethane for 24h; | 100% |
toluene-4-sulfonic acid
{tert-butoxycarbonylmethyl-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-hexyl]-amino}-acetic acid tert-butyl ester
Conditions | Yield |
---|---|
In dichloromethane for 24h; | 100% |
toluene-4-sulfonic acid
{tert-butoxycarbonylmethyl-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-amino}-acetic acid tert-butyl ester
Conditions | Yield |
---|---|
In dichloromethane | 100% |
The Molecular Structure of p-Toluenesulfonic acid (CAS NO.104-15-4):
Empirical Formula: C7H8O3S
Molecular Weight: 172.2016
IUPAC Name: 4-methylbenzenesulfonic acid
Appearance: Clear colorless to light yellow solution
Product Categories: FINE Chemical & INTERMEDIATES;Organics
Nominal Mass: 172 Da
Average Mass: 172.2016 Da
Monoisotopic Mass: 172.019414 Da
Index of Refraction: 1.562
Molar Refractivity: 41.72 cm3
Molar Volume: 128.4 cm3
Surface Tension: 48.2 dyne/cm
Density: 1.34 g/cm3
Boiling point: 116 ºC
Refractive index: 1.3825-1.3845
Flash point: 41 ºC
Storage temp: Flammables area
Water Solubility: soluble
InChI
InChI=1/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10)
Smiles
S(c1ccc(C)cc1)(O)(=O)=O
It is abbreviated as TsOH,it is white solid , soluble in water, alcohols, and other polar organic solvents. Most often, TsOH refers to the monohydrate, TsOH.H2O.
p-Toluenesulfonic acid (CAS NO.104-15-4) is used for pharmaceutical, pesticide, dyestuff, also used in plastics and detergent and printing coatings.
p-Toluenesulfonic acid (CAS NO.104-15-4) is prepared on an industrial scale by the sulfonation of toluene. Common impurities include benzenesulfonic acid and sulfuric acid. Impurities can be removed by recrystallization from concentrated hydrochloric acid followed by azeotropic drying.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
quail | LD50 | oral | > 316mg/kg (316mg/kg) | Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982. | |
rat | LD50 | oral | 2480mg/kg (2480mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1055, 1986 |
Hazard Codes: C
Risk Statements: 34-10
R34: Causes burns
R10: Flammable
Safety Statements: 45-26-23
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S23: Do not breathe vapour
RIDADR: 2585
HazardClass: 8
PackingGroup: III
p-Toluenesulfonic acid (CAS NO.104-15-4) is also called as 4-Methylbenzenesulfonic acid ; 4-Toluenesulfonic acid ; Benzenesulfonic acid, 4-methyl- ; Toluene sulfonic acid ; 4-Methylbenzenesulfonic acid ; 4-Toluenesulfonic acid ; Benzenesulfonic acid, 4-methyl- ; Eltesol ; Kyselina p-toluenesulfonova ; Methylbenzenesulfonic acid ; Toluenesulfonic acid ; Toluenesulfonic acid (VAN) ; p-Toluene sulfonate ; p-Toluenesulphonic acid ; p-Toluolenesulfonic acid ; Toluene-4-sulphonic acid ; Benzenesulfonic acid, 4-methyl- ; Toluenesulfonic acid ; p-Toluenesulfonic acid .
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