98-59-9

Basic information

• Product Name: Tosyl chloride
• Synonyms: 4-Tosyl chloride;Benzenesulfonylchloride,4-methyl-;m-methylbenzenesulfonylchloride;para-toluenesulfochloride;para-toluenesulfonchloride;p-Methylbenzenesulfonyl chloride;p-methylbenzenesulfonylchloride;p-Methylphenylsulfonyl chloride
• CAS NO: 98-59-9
• Molecular Formula: C₇H₇ClO₂S
• Molecular Weight: 190.65
• EINECS: 202-684-8
• Product Categories: Benzene derivatives;FINE Chemical & INTERMEDIATES;Protection & Derivatization Reagents (for Synthesis);Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;synthesis of medicines
• Mol File: 98-59-9.mol
• Article Data: 111

Chemical Properties

• Melting Point: 65-69 °C(lit.)
• Boiling Point: 134 °C10 mm Hg(lit.)
• Flash Point: 128 °C
• Appearance: White/Crystalline Powder
• Density: 1,006 g/cm3
• Vapor Pressure: 1 mm Hg ( 88 °C)
• Refractive Index: 1.545
• Storage Temp.: Store at RT.
• Solubility: methylene chloride: 0.2 g/mL, clear
• Water Solubility: hydrolyses
• Sensitive: Moisture Sensitive
• Stability: Stable. Substances to be avoided include strong bases and strong oxidizing agents and water. Moisture sensitive.
• Merck: 14,9534
• BRN: 607898
• CAS DataBase Reference: Tosyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Tosyl chloride(98-59-9)
• EPA Substance Registry System: Tosyl chloride(98-59-9)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-29-41-38
• Safety Statements: 26-36/37/39-45-27-39
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 1
• RTECS: DB8929000
• F: 9-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 98-59-9(Hazardous Substances Data)

Usage

Chemical Description

Tosyl chloride is a colorless liquid that is commonly used as a reagent in organic synthesis to introduce the tosyl (Ts) functional group (-SO2C6H4CH3) into organic molecules.

Chemical Description

Tosyl chloride is used to tosylate the free hydroxyl group of a compound.

InChI:InChI=1/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3

Synthetic route

para-thiocresol (106-45-6) → p-toluenesulfonyl chloride (98-59-9)

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 (15404-00-9) → p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
With sulfuryl dichloride; triphenylphosphine In dichloromethane for 1h; Ambient temperature;	99%

p-toluidine (106-49-0) → p-toluenesulfonyl chloride (98-59-9)

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

di(p-tolyl) disulfide (103-19-5) → p-toluenesulfonyl chloride (98-59-9)

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%

toluene-4-sulfonic acid (104-15-4) → p-toluenesulfonyl chloride (98-59-9)

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 (146404-41-3) → 1-chloro-4-(2-chloroethyl)benzene (32327-70-1) + p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran for 16h; Ambient temperature; Irradiation;	A 95% B n/a

sodium tosylate (657-84-1) → p-toluenesulfonyl chloride (98-59-9)

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%

sodium benzenesulfonate (873-55-2) → p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
With chlorine In water; toluene Product distribution / selectivity;	93.9%

2-chloro-1,3-dimethylimidazolinium chloride (37091-73-9) → p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
With toluene-4-sulfonic acid In toluene	93.2%

phenyl benzenesulfonate (4358-63-8) + 4-methylphenylboronic acid (5720-05-8) → p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
With phenylchlorosulfate; C43H43NO3PPdS; sodium carbonate In acetone at 20 - 50℃; Inert atmosphere; Sealed tube;	93%

toluene (108-88-3) → p-toluenesulfonyl chloride (98-59-9)

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 (61124-61-6) → p-toluenesulfonyl hydrazide hydrochloride + 5-Benzyl-1,2,3-thiadiazole (80491-28-7) + p-toluenesulfonyl chloride (98-59-9)

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 (146404-40-2) → 1-Chlorohexadecan (4860-03-1) + p-toluenesulfonyl chloride (98-59-9)

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 (5362-76-5) → toluene-4-sulfonamide (70-55-3) + p-toluenesulfonyl chloride (98-59-9) + 4-(2-Chloro-2-methyl-propyl)-[1,2,3]thiadiazole + 5-(1-Chloro-1-methyl-ethyl)-4-methyl-[1,2,3]thiadiazole

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 (1666-13-3) + toluene-4-sulfonic acid hydrazide (1576-35-8) → p-tolyl benzeneselenosulfonate (68819-94-3) + p-toluenesulfonyl chloride (98-59-9)

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 (1950-78-3) + triphenyl(phenylazo)methane (981-18-0) → iodobenzene (591-50-4) + di(4-methyl)phenylthiosulfonate (2943-42-2) + p-toluenesulfonylanhydride (4124-41-8) + p-tolyl triphenylmethyl sulphone (42756-18-3) + chlorobenzene (108-90-7) + p-toluenesulfonyl chloride (98-59-9)

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 (141666-87-7) → p-toluenesulfonyl chloride (98-59-9) + 1-(2-Chloroethyl)-4-methoxybenzene (18217-00-0)

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran for 16h; Ambient temperature; Irradiation;	A n/a B 82%

p-toluene sulfinic acid (536-57-2) → p-toluenesulfonyl chloride (98-59-9)

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

morpholine (110-91-8) → 2(3H)-Benzothiazolone (934-34-9) + p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
In pyridine 1)50 deg C, 2h 2)room temp., 20h;	A 13% B 81%

toluene (108-88-3) → p-toluenesulfonyl chloride (98-59-9) + Toluene-2-sulfonyl chloride (133-59-5)

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 (41780-85-2) → toluene-4-sulfonamide (70-55-3) + p-toluenesulfonyl chloride (98-59-9) + 4-(2-Chloro-cyclohexyl)-[1,2,3]thiadiazole

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%

meta-hydroxybenzaldehyde (100-83-4) → p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
With potassium carbonate	77%

4-chloromorpholine (23328-69-0) + p-toluene sulfinic acid (536-57-2) → 4-tosylmorpholine (6339-26-0) + p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
In dichloromethane for 0.5h; Ambient temperature;	A 76% B 10%

sodium 4-methylbenzenesulfinate (824-79-3) → p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
With pyridine; (Dichloroiodo)benzene In 1,2-dichloro-ethane at 20 - 88℃; for 0.0166667h; Inert atmosphere; Reflux;	74%

cis-2-hydroxymethyl-1-(2,4-dimethoxybenzyl)-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine → cis-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxo-2-azetidinylmethyl mesylate + p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
	A 73% B n/a

N,N'-bis(p-toluenesulfonyl)hydroxylamine (56410-24-3) → bis(4-methylphenylsulfonyl)amino 4-methylbenzenesulfonate (62419-04-9) + toluene-4-sulfonic acid (104-15-4) + p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
With air In chloroform for 12h; Product distribution; Mechanism; Ambient temperature; various reaction conditions;	A 20% B 70% C 5%

C19H34N2O2S (151259-26-6) → p-toluenesulfonyl chloride (98-59-9) + 1-chlorododecane (112-52-7)

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran for 16h; Ambient temperature; Irradiation;	A n/a B 68%

toluene-p-sulfonyl bromide (1950-69-2) + triphenyl(phenylazo)methane (981-18-0) → bromobenzene (108-86-1) + di(4-methyl)phenylthiosulfonate (2943-42-2) + p-tolyl triphenylmethyl sulphone (42756-18-3) + chlorobenzene (108-90-7) + p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
In tetrachloromethane for 30h; Product distribution; Heating;	A 67% B n/a C 56% D 6% E n/a

4-methylbenzenesulfinyl chloride (10439-23-3) + but-3-en-1-ynyl-trimethyl-silane (2696-32-4) → p-toluenesulfonyl chloride (98-59-9) + [3-Chloro-4-(toluene-4-sulfinyl)-but-1-ynyl]-trimethyl-silane + [1-Chloro-4-(toluene-4-sulfinyl)-buta-1,2-dienyl]-trimethyl-silane

Conditions	Yield
aluminium trichloride In diethyl ether Ambient temperature;	A n/a B 66% C n/a

Tetrahydrofurfuryl alcohol (97-99-4) + p-toluenesulfonyl chloride (98-59-9) → rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (34583-63-6)

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 (504-29-0) + p-toluenesulfonyl chloride (98-59-9) → N-(2-pyridyl)-p-toluenesulfonamide (52776-76-8)

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 (578-66-5) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-quinolin-8-yl-benzenesulfonamide (10304-39-9)

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%

tryptamine (61-54-1) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl tryptamine (86658-78-8)

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%

m-Anisidine (536-90-3) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl-m-anisidine (58750-87-1)

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 (551-93-9) + p-toluenesulfonyl chloride (98-59-9) → N-(2-acetylphenyl)-4-methylbenzenesulfonamide (1859-70-7)

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%

1-amino-naphthalene (134-32-7) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl-1-naphthylamine (18271-17-5)

Conditions	Yield
With triethylamine In dichloromethane at 4℃;	100%
With pyridine	98%
at 20℃; for 0.166667h;	94%

4-Aminobiphenyl (92-67-1) + p-toluenesulfonyl chloride (98-59-9) → N-([1,1'-biphenyl]-4-yl)-4-methylbenzenesulfonamide (65690-69-9)

Conditions	Yield
With triethylamine In dichloromethane at 4℃;	100%
With pyridine at 0 - 20℃; for 15h; Inert atmosphere;	75%
With pyridine

cyclohexylamine (108-91-8) + p-toluenesulfonyl chloride (98-59-9) → N-cyclohexyl-p-toluenesulfonamide (80-30-8)

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 (106-49-0) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-(4-methylphenyl)benzenesulfonamide (599-86-0)

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 (106-47-8) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-(4-chlorophenyl)benzenesulfonamide (2903-34-6)

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 (104-94-9) + p-toluenesulfonyl chloride (98-59-9) → N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide (1150-26-1)

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 (90-41-5) + p-toluenesulfonyl chloride (98-59-9) → N-biphenyl-2-yl-4-methylbenzenesulfonamide (24310-30-3)

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 (141-43-5) + p-toluenesulfonyl chloride (98-59-9) → N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide (14316-14-4)

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 (110-58-7) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-pentylbenzenesulfonamide (106011-68-1)

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 (107-19-7) + p-toluenesulfonyl chloride (98-59-9) → propargyl p-toluenesulfonate (6165-76-0)

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 (108-69-0) + p-toluenesulfonyl chloride (98-59-9) → N-(3,5-dimethylphenyl)-4-methyl-benzenesulfonamide (114097-28-8)

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 (99-98-9) + p-toluenesulfonyl chloride (98-59-9) → N-(4-(dimethylamino)phenyl)-4-methylbenzenesulfonamide (19766-55-3)

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 (100-01-6) + p-toluenesulfonyl chloride (98-59-9) → N-(4-nitrophenyl)-4-methylbenzenesulfonamide (734-25-8)

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 (88-74-4) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-(2-nitrophenyl)benzene sulfonamide (6380-13-8)

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 (124-40-3) + p-toluenesulfonyl chloride (98-59-9) → N,N,4-trimethylbenzenesulfonamide (599-69-9)

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 (75-31-0) + p-toluenesulfonyl chloride (98-59-9) → N-isopropyl-p-toluenesulfonamide (21230-07-9)

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%

ethylenediamine (107-15-3) + p-toluenesulfonyl chloride (98-59-9) → ditosylethylenediamine (4403-78-5)

Conditions	Yield
In pyridine at 20℃;	100%
With pyridine at 0 - 20℃;	95%
With sodium hydroxide In diethyl ether at 20℃;	94%

Trimethylenediamine (109-76-2) + p-toluenesulfonyl chloride (98-59-9) → N,N'-ditoluenesulfonyl-1,3-diaminopropane (53364-99-1)

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%

aniline (62-53-3) + p-toluenesulfonyl chloride (98-59-9) → phenyl toluenesulfonamide (68-34-8)

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 (134-20-3) + p-toluenesulfonyl chloride (98-59-9) → methyl N-tosylanthranilate (50998-74-8)

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 (110-80-5) + p-toluenesulfonyl chloride (98-59-9) → 2-ethoxyethyl p-toluenesulfonate (17178-11-9)

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 (100-02-7) + p-toluenesulfonyl chloride (98-59-9) → 4-nitrophenyl 4-methylbenzenesulfonate (1153-45-3)

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 (77-85-0) + p-toluenesulfonyl chloride (98-59-9) → 2-methyl-2-((tosyloxy)methyl)propane-1,3-diyl bis(4-methylbenzenesulfonate) (2387-43-1)

Conditions	Yield
With pyridine at 20℃; for 16h; Inert atmosphere;	100%
With pyridine at 0 - 20℃;	90%
With pyridine In chloroform	81%

2-Phenoxyethanol (122-99-6) + p-toluenesulfonyl chloride (98-59-9) → 2-phenoxyethanol tosylate (43224-81-3)

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%

Upstream product

• 536-57-2 p-toluene sulfinic acid 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 657-84-1 sodium tosylate 
• 104-15-4 toluene-4-sulfonic acid 
• 106-45-6 para-thiocresol 
• 108-88-3 toluene 
• 110-91-8 morpholine 
• 2156-71-0 N-chloropiperidine 
• 23328-69-0 4-chloromorpholine 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 2696-32-4 but-3-en-1-ynyl-trimethyl-silane 
• 4911-58-4 5,5-dimethyl-hex-1-en-3-yne 
• 18387-62-7 1-(trimethylsilyl)-3-penten-1-yne 
• 64-18-6 formic acid 

Downstream Products

• 910887-17-1 methyl-[O²,O³,O⁶-tribenzoyl-O⁴-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 185115-20-2 methyl-[O²,O³,O⁶-tribenzoyl-O⁴-(toluene-4-sulfonyl)-β-D-galactopyranoside] 
• 19467-77-7 methyl 2,3,6-tri-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 1153940-62-5 methyl-[O²,O³,O⁴-tribenzoyl-O⁶-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 19186-53-9 methyl-[tetrakis-O-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 40519-00-4 2,3-O-Isopropylidene-5-O-(p-tolylsulfonyl)-D-ribono-1,4-lactone 
• 3634-89-7 N-(p-toluenesulfonyl)aziridine 
• 20999-32-0 4-chlorobutyl 4-methylbenzenesulfonate 
• 6435-78-5 N-tosylpyrrolidine 
• 92948-25-9 5-chloropentyl 4-methylbenzenesulfonate 
• 27106-51-0 1-tosylpiperazine 
• 17046-84-3 1,4-bis-(toluene-4-sulfonyl)-piperazine 
• 34583-63-6 rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate 
• 97986-34-0 toluene-4-sulfonic acid tetrahydropyran-4-yl ester 

Relevant articles and documents

Facile synthesis of sulfonyl chlorides

A method for the synthesis of sulfonyl chlorides and bromides from the corresponding sulfonate salts is described. The method gives good yields of the acid halides under very mild conditions, and is compatible with both acid and base sensitive functionalities.

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts

We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.

Method for continuously synthesizing P-toluenesulfonyl chloride

The method comprises the following steps: toluene, sulfur trioxide, chlorosulfonic acid, an organic base and a solvent are mixed in first static mixers, and then pumped into first microreactors to react. The first Micro-reactor outlet discharged first reaction mixture flows into second static mixer and mixed with sulfur trioxide, chlorosulfonic acid, low carbon chain fatty acid and solvent pumped into second static mixers respectively, and the resulting mixed materials are pumped into second microreactors to react. The second The secondary reaction mixture discharged from the microreactor was cooled, crystallized and isolated to yield p-toluenesulfonyl chloride as a product. To the method, the production efficiency is greatly improved; due to the addition of the sulfone inhibitor, the problems that a large amount of sulfone substances and polysulfonate are easily generated by sulfonation of sulfur trioxide are effectively solved, and hydrogen chloride gas is prevented from being generated.