Conditions | Yield |
---|---|
With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0166667h; | 99% |
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; tetrabutyl-ammonium chloride; water In acetonitrile at 0 - 20℃; for 0.333333h; | 98% |
With trichloroisocyanuric acid; water In acetonitrile at 0 - 20℃; for 0.333333h; | 98% |
triethylammonium toluene-p-sulfonate
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With sulfuryl dichloride; triphenylphosphine In dichloromethane for 1h; Ambient temperature; | 99% |
Conditions | Yield |
---|---|
Stage #1: p-toluidine With hydrogenchloride; acetic acid; sodium nitrite In water; acetonitrile at 0 - 5℃; Stage #2: With sulfur dioxide; copper dichloride In water; acetonitrile at 20℃; for 16h; | 99% |
Stage #1: p-toluidine With hydrogenchloride; sodium nitrite Stage #2: With sulfur dioxide; copper(l) chloride In acetone |
Conditions | Yield |
---|---|
With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0166667h; | 98% |
With Oxone; potassium chloride In water at 20℃; for 0.166667h; | 96% |
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; tetrabutyl-ammonium chloride; water In acetonitrile at 0 - 20℃; for 0.333333h; | 95% |
Conditions | Yield |
---|---|
With 1,3,5-trichloro-2,4,6-triazine; triethylamine In acetone for 20h; Heating; | 96% |
Stage #1: toluene-4-sulfonic acid With potassium phosphate; bis(trichloromethyl) carbonate In dichloromethane at 0 - 5℃; for 0.0833333h; Stage #2: With triethylamine In dichloromethane at 20℃; for 0.5h; | 96% |
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; potassium chloride at 25℃; for 0.0333333h; Neat (no solvent); | 94% |
C15H17ClN2O2S
A
1-chloro-4-(2-chloroethyl)benzene
B
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With N-chloro-succinimide In tetrahydrofuran for 16h; Ambient temperature; Irradiation; | A 95% B n/a |
Conditions | Yield |
---|---|
With 1,3,5-trichloro-2,4,6-triazine; 18-crown-6 ether In acetone for 20h; Heating; | 94% |
Stage #1: sodium tosylate With potassium phosphate; bis(trichloromethyl) carbonate In dichloromethane at 0 - 5℃; for 0.0833333h; Stage #2: With triethylamine In dichloromethane at 20℃; for 0.5h; | 93% |
With trichlorophosphate In sulfolane; acetonitrile at 68 - 72℃; for 0.666667h; | 87% |
Conditions | Yield |
---|---|
With chlorine In water; toluene Product distribution / selectivity; | 93.9% |
2-chloro-1,3-dimethylimidazolinium chloride
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene | 93.2% |
phenyl benzenesulfonate
4-methylphenylboronic acid
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With phenylchlorosulfate; C43H43NO3PPdS; sodium carbonate In acetone at 20 - 50℃; Inert atmosphere; Sealed tube; | 93% |
Conditions | Yield |
---|---|
With chlorosulfonic acid at 0℃; for 4h; | 92% |
With chlorosulfonic acid at 0 - 20℃; | 84.21% |
With chlorosulfonic acid |
3-phenylpropanal p-tosylhydrazone
B
5-Benzyl-1,2,3-thiadiazole
C
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With disulfur dichloride In dichloromethane at 20℃; for 0.5h; Product distribution; other reagents (SOCl2, SCl2) and time; | A n/a B 89% C n/a |
1-tosyl-1-hexadecylhydrazine
A
1-Chlorohexadecan
B
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With N-chloro-succinimide In tetrahydrofuran for 16h; Ambient temperature; Irradiation; | A 88% B n/a |
With N-chloro-succinimide In tetrahydrofuran for 16h; Product distribution; Mechanism; Ambient temperature; Irradiation; reactions of N-substituted-N-tosylhydrazines with NCS and NBS; | A 88% B n/a |
mesityl oxide p-tosylhydrazone
A
toluene-4-sulfonamide
B
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With sulfur dichloride In dichloromethane at 20℃; for 0.5h; Product distribution; other reagents (SOCl2, S2Cl2), products and time; | A n/a B n/a C 9% D 85% |
diphenyl diselenide
toluene-4-sulfonic acid hydrazide
A
p-tolyl benzeneselenosulfonate
B
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With sulfuryl dichloride; triethylamine In pyridine; dichloromethane at 0℃; Product distribution; various reagents for preparation of diverse selenosulfonates; mechanism is proposed; | A 83% B 11% |
p-toluenesulfonyl iodide
triphenyl(phenylazo)methane
A
iodobenzene
B
di(4-methyl)phenylthiosulfonate
C
p-toluenesulfonylanhydride
D
p-tolyl triphenylmethyl sulphone
E
chlorobenzene
F
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
In tetrachloromethane at 0℃; for 2h; Product distribution; | A 82% B n/a C n/a D 78% E 1% F n/a |
1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine
A
p-toluenesulfonyl chloride
B
1-(2-Chloroethyl)-4-methoxybenzene
Conditions | Yield |
---|---|
With N-chloro-succinimide In tetrahydrofuran for 16h; Ambient temperature; Irradiation; | A n/a B 82% |
Conditions | Yield |
---|---|
With tert-butylhypochlorite In dichloromethane for 2h; Ambient temperature; chloramine-T, CH2Cl2, RT; | 81% |
With water; chlorine | |
With N-chloro-succinimide In tetrahydrofuran Ambient temperature; Irradiation; Yield given; | |
Multi-step reaction with 2 steps 1: 81 percent / CH2Cl2 / 2 h / Ambient temperature 2: 1.) n-butyllithium, 2.) SO2Cl2 / 1.) THF, hexane, -78 deg C, 2.) -78 deg C, 20 min View Scheme |
Conditions | Yield |
---|---|
In pyridine 1)50 deg C, 2h 2)room temp., 20h; | A 13% B 81% |
Conditions | Yield |
---|---|
With chlorosulfonic acid; sodium chloride at -0.16℃; | A 80% B 20% |
With chlorosulfonic acid for 3h; Cooling with ice; | A n/a B 72.04% |
With sulfuric acid; sodium chloride Edukt 4: SO3; |
1-acetylcyclohexene p-tosylhydrazone
A
toluene-4-sulfonamide
B
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With sulfur dichloride In dichloromethane at 20℃; for 0.5h; Product distribution; other reagents (SOCl2, S2Cl2) and time; | A n/a B n/a C 80% |
Conditions | Yield |
---|---|
With potassium carbonate | 77% |
4-chloromorpholine
p-toluene sulfinic acid
A
4-tosylmorpholine
B
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; Ambient temperature; | A 76% B 10% |
Conditions | Yield |
---|---|
With pyridine; (Dichloroiodo)benzene In 1,2-dichloro-ethane at 20 - 88℃; for 0.0166667h; Inert atmosphere; Reflux; | 74% |
B
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
A 73% B n/a |
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 N-chloro-succinimide In tetrahydrofuran for 16h; Ambient temperature; Irradiation; | A n/a B 68% |
toluene-p-sulfonyl bromide
triphenyl(phenylazo)methane
A
bromobenzene
B
di(4-methyl)phenylthiosulfonate
C
p-tolyl triphenylmethyl sulphone
D
chlorobenzene
E
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
In tetrachloromethane for 30h; Product distribution; Heating; | A 67% B n/a C 56% D 6% E n/a |
4-methylbenzenesulfinyl chloride
but-3-en-1-ynyl-trimethyl-silane
A
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
aluminium trichloride In diethyl ether Ambient temperature; | A n/a B 66% C n/a |
Tetrahydrofurfuryl alcohol
p-toluenesulfonyl chloride
rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 1h; | 100% |
With potassium hydroxide | 93% |
With potassium iodide; silver(l) oxide In dichloromethane at 40℃; | 91% |
2-aminopyridine
p-toluenesulfonyl chloride
N-(2-pyridyl)-p-toluenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
at 20℃; for 0.1h; | 88% |
With sodium carbonate In water | 82.1% |
8-amino quinoline
p-toluenesulfonyl chloride
4-methyl-N-quinolin-8-yl-benzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With pyridine at 130℃; for 0.05h; Microwave irradiation; Inert atmosphere; | 97% |
With pyridine at 130℃; for 0.166667h; | 90% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; | 99% |
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 99% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 28h; | 100% |
With triethylamine In dichloromethane at 4℃; | 100% |
With triethylamine In tetrahydrofuran at 20℃; for 15h; | 95% |
2-aminoacetophenone
p-toluenesulfonyl chloride
N-(2-acetylphenyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 10.5h; | 100% |
With triethylamine In dichloromethane at 4℃; | 100% |
With pyridine In dichloromethane at 20℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With pyridine | 98% |
at 20℃; for 0.166667h; | 94% |
4-Aminobiphenyl
p-toluenesulfonyl chloride
N-([1,1'-biphenyl]-4-yl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With pyridine at 0 - 20℃; for 15h; Inert atmosphere; | 75% |
With pyridine |
cyclohexylamine
p-toluenesulfonyl chloride
N-cyclohexyl-p-toluenesulfonamide
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.5h; Inert atmosphere; | 100% |
With pyridine at 0 - 25℃; Inert atmosphere; Schlenk technique; | 99% |
With triethylamine In tetrahydrofuran at 0 - 20℃; | 95% |
p-toluidine
p-toluenesulfonyl chloride
4-methyl-N-(4-methylphenyl)benzenesulfonamide
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 16h; | 100% |
With pyridine at 0 - 25℃; | 100% |
In water at 110℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction; | 98% |
4-chloro-aniline
p-toluenesulfonyl chloride
4-methyl-N-(4-chlorophenyl)benzenesulfonamide
Conditions | Yield |
---|---|
In pyridine; acetonitrile at 20℃; for 16h; | 100% |
In ethanol; water at 25℃; for 0.333333h; | 96% |
With (Na1752K0.144Ca0365Mg0.065)(Al2044Si2774O96)*19.16H2O In ethanol at 25 - 30℃; for 0.25h; Sonication; Green chemistry; | 95% |
4-methoxy-aniline
p-toluenesulfonyl chloride
N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With pyridine for 16h; Reflux; | 97% |
With dendritic fibrous nanosilica KCC-1 3-aminopropyl-functionalized supported on Fe3O4 magnetic nanocatalyst In water at 20℃; for 0.5h; Solvent; Temperature; Reagent/catalyst; Time; Green chemistry; | 97% |
2-phenylaniline
p-toluenesulfonyl chloride
N-biphenyl-2-yl-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With sodium hydrogencarbonate In water; acetone at 25℃; for 0.25h; | 97% |
With pyridine at 0 - 25℃; for 1h; | 92% |
ethanolamine
p-toluenesulfonyl chloride
N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; for 24h; | 99% |
With pyridine at 5 - 20℃; | 96% |
1-pentanamine
p-toluenesulfonyl chloride
4-methyl-N-pentylbenzenesulfonamide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; | 100% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 89% |
With triethylamine In dichloromethane at 0℃; for 0.0833333h; | 85% |
propargyl alcohol
p-toluenesulfonyl chloride
propargyl p-toluenesulfonate
Conditions | Yield |
---|---|
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 17h; | 100% |
With potassium hydroxide In diethyl ether at -5 - 20℃; | 96% |
With potassium hydroxide In diethyl ether at -5 - 0℃; for 0.5h; | 95% |
3,5-dimethylaminoaniline
p-toluenesulfonyl chloride
N-(3,5-dimethylphenyl)-4-methyl-benzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With silica gel at 20℃; | 95% |
With triethylamine In dichloromethane at 0 - 20℃; | 82% |
4-amino-N,N-dimethylaniline
p-toluenesulfonyl chloride
N-(4-(dimethylamino)phenyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With pyridine for 1h; Reflux; | 100% |
With caesium carbonate In acetonitrile at 25℃; for 0.333333h; | 93% |
indium In acetonitrile at 20℃; for 6h; | 90% |
4-nitro-aniline
p-toluenesulfonyl chloride
N-(4-nitrophenyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With (Na1752K0.144Ca0365Mg0.065)(Al2044Si2774O96)*19.16H2O In ethanol at 25 - 30℃; for 2h; Sonication; Green chemistry; | 96% |
With pyridine In dichloromethane at 20℃; for 12h; | 94% |
2-nitro-aniline
p-toluenesulfonyl chloride
4-methyl-N-(2-nitrophenyl)benzene sulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With pyridine In dichloromethane at 20℃; for 48h; | 90% |
With pyridine In dichloromethane at 20℃; for 16h; | 75% |
dimethyl amine
p-toluenesulfonyl chloride
N,N,4-trimethylbenzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 25℃; for 1h; | 100% |
99% | |
With cesium fluoride supported on Celite at 50℃; for 0.75h; chemoselective reaction; | 91% |
isopropylamine
p-toluenesulfonyl chloride
N-isopropyl-p-toluenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
With pyridine; dmap In dichloromethane at 0 - 20℃; for 16h; | 99% |
With pyridine at 0 - 25℃; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
In pyridine at 20℃; | 100% |
With pyridine at 0 - 20℃; | 95% |
With sodium hydroxide In diethyl ether at 20℃; | 94% |
Trimethylenediamine
p-toluenesulfonyl chloride
N,N'-ditoluenesulfonyl-1,3-diaminopropane
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 0.2℃; for 3h; Inert atmosphere; | 100% |
at 80℃; for 0.5h; | 95% |
With potassium carbonate In tetrahydrofuran; water at 23℃; for 10h; | 95% |
Conditions | Yield |
---|---|
With pyridine for 16h; Reflux; | 100% |
With pyridine In dichloromethane at 20℃; for 16h; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; | 100% |
2-carbomethoxyaniline
p-toluenesulfonyl chloride
methyl N-tosylanthranilate
Conditions | Yield |
---|---|
In pyridine at 25℃; | 100% |
Stage #1: 2-carbomethoxyaniline With pyridine In dichloromethane at 25℃; for 1h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 25℃; for 24h; Inert atmosphere; | 99% |
In pyridine at 0℃; for 1h; | 98% |
2-ethoxy-ethanol
p-toluenesulfonyl chloride
2-ethoxyethyl p-toluenesulfonate
Conditions | Yield |
---|---|
With pyridine at 0℃; | 100% |
With sodium hydroxide In tetrahydrofuran; water | 85% |
With triethylamine In dichloromethane at 20℃; for 4h; | 81.1% |
4-nitro-phenol
p-toluenesulfonyl chloride
4-nitrophenyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
Stage #1: 4-nitro-phenol; p-toluenesulfonyl chloride With potassium carbonate In acetone at 20 - 25℃; for 2.5h; Stage #2: With hydrogenchloride In water; acetone | 100% |
With triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere; | 99% |
With potassium carbonate for 0.0833333h; microwave irradiation; | 98% |
2-(hydroxymethyl)-2-methylpropane-1,3-diol
p-toluenesulfonyl chloride
2-methyl-2-((tosyloxy)methyl)propane-1,3-diyl bis(4-methylbenzenesulfonate)
Conditions | Yield |
---|---|
With pyridine at 20℃; for 16h; Inert atmosphere; | 100% |
With pyridine at 0 - 20℃; | 90% |
With pyridine In chloroform | 81% |
Conditions | Yield |
---|---|
Stage #1: 2-Phenoxyethanol; p-toluenesulfonyl chloride With dmap In dichloromethane at 20℃; Stage #2: With triethylamine In dichloromethane at 20℃; | 100% |
With pyridine | 86% |
With pyridine at 20℃; for 4h; | 24% |
IUPAC Name: 4-Methylbenzenesulfonyl chloride
Following is the structure of Tosyl chloride (CAS NO.98-59-9):
Empirical Formula: C7H7ClO2S
Molecular Weight: 190.6473
EINECS: 202-684-8
Index of Refraction: 1.545
Molar Refractivity: 45.02 cm3
Molar Volume: 142.3 cm3
Storage temp.: Store at RT.
Water Solubility: hydrolyses
Density: 1.339 g/cm3
Flash Point: 114.3 °C
Melting point: 65-69 °C(lit.)
Surface Tension: 41 dyne/cm
Enthalpy of Vaporization: 48.3 kJ/mol
Boiling Point: 265.3 °C at 760 mmHg
Vapour Pressure: 0.0151 mmHg at 25 °C
Appearance: White to yellow solid
Solubility of Tosyl chloride (CAS NO.98-59-9): Methylene chloride: 0.2 g/mL, clear
Product Categories of Tosyl chloride (CAS NO.98-59-9): Benzene derivatives; FINE Chemical & INTERMEDIATES; Protection & Derivatization Reagents (for Synthesis); Sulfur Compounds (for Synthesis); Synthetic Organic Chemistry
Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)Cl
InChI: InChI=1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3
InChIKey: YYROPELSRYBVMQ-UHFFFAOYSA-N
Tosyl chloride (CAS NO.98-59-9) can be used as analytics reagents,and organic synthesis etc.
Hazard Codes: C
Risk Statements 34-29
R34:Causes burns.
R29:Contact with water liberates toxic gas.
Safety Statements 26-36/37/39-45-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S27:Take off immediately all contaminated clothing.
RIDADR: UN 3261 8/PG 2
WGK Germany: 1
F: 9-21
Hazard Note: Corrosive
HazardClass: 8
PackingGroup: II
HS Code: 29049020
Hazardous Substances Data: 98-59-9(Hazardous Substances Data)
Tosyl chloride , its cas register number is 98-59-9. It also can be called 4-Toluene sulfochloride ; 4-Methylbenzenesulfonyl chloride ; p-Toluenesulfonyl chloride ; Toluene-4-sulfonyl chloride ; 4-Toluolsulfonyl chloride ; and p-Tosyl Chloride .
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