104-15-4

Basic information

• Product Name: p-Toluenesulfonic acid
• Synonyms: TL65;TL65LS;PARATOLUENE SULPHONIC ACID;P-TOLUENESULFONIC ACID;PTS ACID;P-TOLUENE SULPHONIC ACID;TSA-65IP;TSA-65M
• CAS NO: 104-15-4
• Molecular Formula: C₇H₈O₃S
• Molecular Weight: 172.2
• EINECS: 203-180-0
• Product Categories: FINE Chemical & INTERMEDIATES;Organics;curing agent
• Mol File: 104-15-4.mol
• Article Data: 298

Chemical Properties

• Melting Point: 106~107℃
• Boiling Point: 116 °C
• Flash Point: 41 °C
• Appearance: Clear colorless to light yellow/Solution
• Density: 1.07
• Vapor Pressure: 69.8Pa at 20℃
• Refractive Index: 1.3825-1.3845
• Storage Temp.: Flammables area
• PKA: -0.43±0.50(Predicted)
• Water Solubility: soluble
• CAS DataBase Reference: p-Toluenesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: p-Toluenesulfonic acid(104-15-4)
• EPA Substance Registry System: p-Toluenesulfonic acid(104-15-4)

Safety Data

• Hazard Codes: C
• Statements: 34-10
• Safety Statements: 45-26-23
• RIDADR: 2585
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 104-15-4(Hazardous Substances Data)

Usage

Overview

p-toluene sulfonic acid (Its molecular structural formula is p-CH3C6H4SO3H, also known as TsOH, English name is p-toluene sulfonic acid) referred to as PTS, is a non-oxidizing organic acid, white needle or powder crystals, soluble in water, alcohols, ethers and other polar solvents. Easy deliquescence, easy to make wood, cotton fabric dehydration and carbonization, insoluble in benzene and toluene. generating p-cresol when alkali fusion. Commonly, p-toluenesulfonic acid-monohydrate (TsOHH2O) or tetrahydrate (TsOH4H2O) is preferred. Preparation of methyl p-cresol acid in industry is by using concentrated sulfuric acid on the toluene sulfonation of p-toluenesulfonic acid. The preparated p-toluenesulfonic acid often contains benzene sulfonic acid and sulfuric acid impurities, can be purified in recrystallization of concentrated hydrochloric acid, azeotropic drying. p-toluene sulfonic acid is widely used as catalyst agent in the synthesis of pharmaceuticals, pesticides, polymerization stabilizer and organic synthesis (esters, etc.), paint intermediates and resin curing agent. And it is also the commonly used acid catalyst in organic synthesis. It is neutralized with sodium hydroxide and then obtains sodium p-toluene sulfonate, and react with phosphorus pentachloride, can obtains p-toluenesulfonyl chloride. The latter used in the nucleophilic substitution reaction, also used as alcohol hydroxyl protective group. p-CH3C6H4SO3Na + PCl5 →p-CH3C6H4SO2Cl. The use of p-toluenesulfonic acid also catalyzes the protection of dihydrofuran on the alcohol, carboxylic acid esterification, transesterification reaction, making the aldehyde generate acetal.

Refer to quality standards

Item/Index Industrial Grade Pharmaceutical Grade Refined Grade Reagent Grade (Chemically Pure) Content (as C7H8O3S ? H2O)% ≥ 90-93.0 96.0 97.0 98.0 Free acid (H2SO4) ≤% 3.0 0.7 0.5 0.1 Moisture (excluding crystal water) ≤% 4.0 3.5 2.5 1.5 Iron (in Fe ++) ≤ ppm 50 30 30 10 Ignition residue ≤%/0.2 0.2 0.02 Melting point (°C)// 102-105 Ethanol dissolved test/qualified qualified qualified Water dissolution test/qualified qualified qualified

Chemical properties

Colorless monoclinic sheet or columnar crystals. Soluble in ethanol and ether, slightly soluble in water and hot benzene.

Uses

(1) For chemical reagents, but also for dyes, organic synthesis. (2) Used as the intermediates of medicine (such as doxycycline), pesticides (such as dicofol), dyes. Also used in detergents, plastics, coatings and so on. (3) For medicine, pesticides, dyes and detergents, but also for plastics and printing coatings. (4) Widely used in the catalyst synthetic medicine, pesticides, polymerization of the stabilizer and organic synthesis (esters, etc.). Also used as medicine, paint intermediates and resin curing agent.

Production method

By p-toluenesulfonyl chloride hydrolysis derived. Toluene can also be used as raw materials, sulfonated by sulfuric acid derived.

Hazards & Safety Information

Category:Corrosive articles Toxicity classification:Low toxicity Acute toxicity Oral-rat LD50: 2480 mg/kg Flammability hazard characteristics Combustible; fire in the release of toxic sulfur dioxide gas Storage and transportation characteristics Storehouse is ventilates, low temperature and dry; Store with base separately Extinguishing agent Mist water, carbon dioxide, foam

Description

p-Toluene sulfonic acid (PTSA) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H. It is a white solid that is soluble in water, alcohols, and other polar organic solvents. The 4-CH3C6H4SO2- group is known as tosyl group and is often abbreviated as Ts or Tos. Most often, TsOH refers to the monohydrate, TsOH.H2O. TsOH is a strong organic acid, about a million times stronger than benzoic acid. It is one of the few strong acids that is solid and, hence, conveniently weighed. Also, unlike some strong mineral acids (especially nitric acid, sulfuric acid, and per chloric acid), TsOH is non - oxidizing.

Chemical Properties

Clear colorless to light yellow solution

Definition

ChEBI: p-Toluenesulfonic acid is an arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group. It is a member of toluenes and an arenesulfonic acid. It is a conjugate acid of a toluene-4-sulfonate.

Reactions

p-Toluene sulfonic acid may be converted to p-toluene sulfonic anhydride by heating with phosphorus pentoxide. When TsOH is heated with acid and water, a hydrolysis reaction takes place and toluene is formed: CH3C6H4SO3H + H2O → C6H5CH3 + H2SO4 This reaction is general for aryl sulfonic acids, but the rate at which it occurs depends upon the structure of the acid, the temperature and the nature of the catalyzing acid. For example p- TsOH is unaffected by cold concentrated hydrochloric acid, but hydrolyzes when heated to 186°C in concentrated phosphoric acid.

Flammability and Explosibility

Nonflammable

Preparation and handling

TsOH is prepared on an industrial scale by the sulfonation of toluene. It hydrates readily. Common impurities include benzene sulfonic acid and sulfuric acid. Impurities can be removed by recrystallization from its concentrated aqueous solution followed by azeotropic drying with toluene. Toluene sulfonic acid finds use in organic synthesis as an "organic - soluble" acid catalyst. Examples of uses : Acetalization of an aldehyde. Esterification of carboxylic acids. Trans esterification of an ester.

Tosylate esters

Tosylate esters are used as alkylating agents because the tosyl group is electron-with drawing, which makes the tosylate anion a good leaving group. The tosyl group is also a protecting group for alcohols and amines, prepared by combining the alcohol with 4- toluenesulfonyl chloride, usually in an aprotic solvent, often pyridine, the basicity of which activates the reaction. Toluenesulfonate esters undergo nucleophilic attack or elimination. Reduction of tosylate esters gives the hydrocarbon. Thus, tosylation followed by reduction allows for the deoxygenation of alcohols.

InChI:InChI=1/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10)

Synthetic route

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

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%

para-thiocresol (106-45-6) → toluene-4-sulfonic acid (104-15-4)

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 (26177-05-9) → toluene-4-sulfonic acid (104-15-4) + 1-hydroxycarbostyril (58-57-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran for 2h; Product distribution; Ambient temperature;	A n/a B 98%

triethylammonium toluene-p-sulfonate (15404-00-9) → toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
With sulfuric acid In water pH=3;	97.5%

(1,1-dioxido-4-oxo-3-phenyl-4H-thiochromen-2-yl)methyl 4-methylbenzenesulfonate → C16H10O3S (1033736-87-6) + toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
In chloroform-d1 for 0.233333h; Photolysis; Inert atmosphere;	A n/a B 97%

di(p-tolyl) disulfide (103-19-5) → toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
With dihydrogen peroxide; trichlorophosphate In water at 80℃; for 1h; Micellar solution;	94%

toluene (108-88-3) → toluene-4-sulfonic acid (104-15-4)

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 (84877-44-1) → toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
With trifluoroacetic acid In water at 20℃; for 2h;	91%

phenethylamine (64-04-0) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-(2-phenylethyl)benzenesulfonamide (5450-75-9) + toluene-4-sulfonic acid (104-15-4)

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 (478363-68-7) → N-Trifluoroacetyl-1,2,3,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-(6β,8aβ)-6-isoquinolineamine 4-methylbenzenesulfonate + toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
In ethanol; di-isopropyl ether; palladium	A n/a B 90%

1-(p-methylbenzenesulfonoyloxy)-2(1H)-quinolone (26177-05-9) → 2-quinolone (59-31-4, 70254-42-1) + toluene-4-sulfonic acid (104-15-4)

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 (86108-37-4) → 2-methyl-1,1-diphenylpropene (781-33-9) + toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
at 115℃; Product distribution; Rate constant; Thermodynamic data; Ea(excit.), ΔS(excit.);	A 85% B n/a

N'-2-butanylidene-4-methylbenzenesulfonohydrazine (4031-16-7) → toluene-4-sulfonic acid (104-15-4) + butanone (78-93-3)

Conditions	Yield
With molecular sieve; dihydrogen peroxide In methanol for 4h; Mechanism; Heating; other solvent; tosylhydrazones of other ketones;	A n/a B 84%

3,4-dichloro-5-[(4-me thylphenyl)sulfanyl]-2(5H)-furanone → Mucochloric acid (766-40-5) + 3,4-dichloro-5-[(4-methyl phenyl)sulfonyl]-2(5H)-furanone (1610693-10-1) + toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
With dihydrogen peroxide In water; acetic acid at 20℃; for 96h;	A n/a B 83% C n/a

4-tolyl iodide (624-31-7) → toluene-4-sulfonic acid (104-15-4)

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%

di(4-methyl)phenylthiosulfonate (2943-42-2) → toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 2h; Heating;	78%

sodium 4-methylbenzenesulfinate (824-79-3) → toluene-4-sulfonic acid (104-15-4)

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 (73706-60-2) → 4-Methylbiphenyl (644-08-6) + 4-Phenyl-2-butanone (2550-26-7) + 1,4-diphenyl-2-butanone (37985-17-4) + toluene-4-sulfonic acid (104-15-4)

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 (86108-35-2) → 3-methyl-1,2-diphenylbut-2-en-1-one (29689-80-3) + toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
at 130℃; Product distribution; Rate constant; Thermodynamic data; Ea(excit.), ΔS(excit.);	A 74% B n/a

(E)-3-hexenoic acid (1577-18-0) → 5-ethyl-5H-furan-2-one (2407-43-4) + toluene-4-sulfonic acid (104-15-4)

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 (13668-61-6) → 3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (5650-67-9) + toluene-4-sulfonic acid (104-15-4)

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 (3695-77-0) + toluene-p-sulfonyl bromide (1950-69-2) → triphenylmethyl alcohol (76-84-6) + toluene-4-sulfonic acid (104-15-4) + Toluene-4-thiosulfonic acid S-trityl ester (118511-93-6)

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 (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%

sodium tosylate (657-84-1) → toluene-4-sulfonic acid (104-15-4)

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 (27126-76-7) + 5-norbornene-endo-2-carboxylic acid (934-30-5, 1195-12-6, 20507-53-3, 58001-99-3, 67999-50-2, 67999-53-5, 74645-32-2, 108266-75-7, 120-74-1) → Toluene-4-sulfonic acid (1S,3S,6S,7R)-4-oxo-5-oxa-tricyclo[4.3.0.03,7]non-9-yl ester (75759-33-0, 108033-20-1) + toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
In dichloromethane at 0℃;	A 28% B 60%

2,2-Dimethyl-3-phenyl-3-(toluene-4-sulfonyloxy)-propionic acid ethyl ester (81699-64-1) → ethyl isopropylidenephenylacetic carboxylate (6335-78-0) + ethyl 2-methylene-3-phenylbutanoate (81699-67-4) + toluene-4-sulfonic acid (104-15-4) + Ethyl 1-methyl-2-phenylcyclopropane-1-carboxylate (81699-66-3)

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 (14062-05-6) → bis(4-methylphenyl)disulfone (10409-07-1) + toluene-p-sulfonyl bromide (1950-69-2) + toluene-4-sulfonic acid (104-15-4)

Conditions	Yield
With bromine In water; acetonitrile at 20℃;	A 10% B 57% C 20%

3-methoxy-1-methyl-1,2,5,6-tetrahydropyridine (98435-42-8) + toluene-4-sulfonic acid (104-15-4) → 3-methoxy-1-methyl-1,2,5,6-tetrahydropyridinium toluene-p-sulphonate (135625-83-1)

Conditions	Yield
In acetone for 0.25h; educt toluene-p-sulphonic acid: anhydrous;	100%

methyl (+/-)-trans-(2,3)-epoxy butanoate (10133-06-9, 10133-07-0, 10133-45-6, 50468-20-7, 59123-20-5, 83057-88-9, 121252-25-3, 129311-57-5, 136889-92-4, 2980-48-5) + toluene-4-sulfonic acid (104-15-4) → methyl 2-hydroxy-3-(p-tolylsulfonyloxy)butanoate

Conditions	Yield
	100%

Trimethyl orthoacetate (1445-45-0) + toluene-4-sulfonic acid (104-15-4) → methyl p-toluene sulfonate (80-48-8)

Conditions	Yield
at 20℃; for 0.5h;	100%
In dichloromethane for 0.5h; Ambient temperature;	96%

ethanol (64-17-5) + L-phenylalanine (63-91-2) + toluene-4-sulfonic acid (104-15-4) → Phe-OEt * TosOH (5002-64-2)

Conditions	Yield
for 24h; Heating;	100%

L-valine (72-18-4) + 2-methyl-propan-1-ol (78-83-1) + toluene-4-sulfonic acid (104-15-4) → (S)-1-isobutoxy-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate (13018-45-6)

Conditions	Yield
In water; toluene for 24h; Reflux; Dean-Stark;	100%
In benzene Heating;	84%
In benzene Heating;

[bis(acetoxy)iodo]benzene (3240-34-4) + toluene-4-sulfonic acid (104-15-4) → [hydroxy(tosyloxy)iodo]benzene (27126-76-7)

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 (89121-14-2) + toluene-4-sulfonic acid (104-15-4) → Nε-(Benzyloxycarbonyl)-L-lysine 2-(Trimethylsilyl)ethyl Ester p-Toluenesulfonate (89106-04-7)

Conditions	Yield
In benzene for 1h; Heating;	100%

toluene-4-sulfonic acid (104-15-4) + (S)-2-tert-Butoxycarbonylamino-propionic acid 6-((S)-2-tert-butoxycarbonylamino-propionyloxy)-hexa-2,4-diynyl ester (125376-21-8) → (S)-2-Amino-propionic acid 6-((S)-2-amino-propionyloxy)-hexa-2,4-diynyl ester; compound with toluene-4-sulfonic acid (125376-29-6)

Conditions	Yield
With acetic acid at 50℃;	100%

toluene-4-sulfonic acid (104-15-4) + Z-L-Leu-L-Lys(Boc)-L-Lys(Boc)-OPh (136185-16-5) → (S)-2-[(S)-2-((S)-2-Amino-4-methyl-pentanoylamino)-6-tert-butoxycarbonylamino-hexanoylamino]-6-tert-butoxycarbonylamino-hexanoic acid phenyl ester; compound with toluene-4-sulfonic acid

Conditions	Yield
With hydrogen; palladium on activated charcoal for 1.33333h;	100%

toluene-4-sulfonic acid (104-15-4) + Z-L-Ser(tBu)-L-Lys(Boc)-L-Leu-L-Lys(Boc)-L-Lys(Boc)-OPh (136185-19-8) → H-L-Ser(tBu)-L-Lys(Boc)-L-Leu-L-Lys(Boc)-L-Lys(Boc)-OPh*TosOH (136185-33-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 1h;	100%

toluene-4-sulfonic acid (104-15-4) + Z-L-Glu(OtBu)-L-Lys(Boc)-L-Asn-L-Pro-L-Leu-L-Pro-L-Ser(tBu)-OPh (138541-14-7) → H-L-Glu(OtBu)-L-Lys(Boc)-L-Asn-L-Pro-L-Leu-L-Pro-L-Ser(tBu)-OPh*TosOH (138541-36-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 4h;	100%

toluene-4-sulfonic acid (104-15-4) + Z-L-Leu-L-Pro-L-Ser(tBu)-OPh (138541-04-5) → H-L-Leu-L-Pro-L-Ser(tBu)-OPh*TosOH (138541-24-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 1.5h;	100%

toluene-4-sulfonic acid (104-15-4) + Z-L-Thr(tBu)-L-Gln-L-Glu(OtBu)-L-Lys(Boc)-OPh (138541-08-9) → H-L-Thr(tBu)-L-Gln-L-Glu(OtBu)-L-Lys(Boc)-OPh*TosOH (138541-11-4)

Conditions	Yield
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 1h;	100%

toluene-4-sulfonic acid (104-15-4) + α-<2-(trimethylsilyl)ethyl> γ-n-hexadecyl N-(tert-butyloxycarbonyl)-L-glutamate (88887-52-9) → α-<2-(trimethylsilyl)ethyl> γ-n-hexadecyl L-glutamate tosylate (88887-54-1)

Conditions	Yield
In benzene for 1h; Heating;	100%

toluene-4-sulfonic acid (104-15-4) + 2,4-Dioxabicyclo[3.3.1]nonane-1,5-diethanol → C25H32O8S2

Conditions	Yield
	100%

toluene-4-sulfonic acid (104-15-4) + nonafluorobutyliodine(III) bis(trifluoroacetate) (90934-12-6) → perfluorobutane (155819-09-3)

Conditions	Yield
In acetonitrile at 0 - 20℃;	100%
In acetonitrile Ambient temperature;	91%
In acetonitrile at -20 - 20℃; for 1h;	91%

L-leucine (61-90-5) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6) → L-leucine benzyl ester p-toluenesulfonate (1738-77-8)

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 (2481-09-6) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6) → p-Toluenesulfonate of S-tert-Butyl-L-cysteine Benzyl Ester (76499-06-4)

Conditions	Yield
In chloroform for 6h; Heating;	100%

toluene-4-sulfonic acid (104-15-4) + (+/-)-(3R*,4R*,5S*)-5-((1'S*)-azidopropyl)-3-methyl-4-(phenyldimethylsilyl)-dihydrofuran-2-one → (+/-)-(3R*,4R*,5S*)-5-((1'S*)-aminopropyl)-3-methyl-4-(phenyldimethylsilyl)-dihydrofuran-2-one, p-toluenesulphonic acid

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 8h;	100%

L-alanin (56-41-7) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6) → L-alanine benzyl ester p-toluenesulfonate (42854-62-6)

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 (104-15-4) + 4-[3-oxo-3-thiazol-2-yl-2-(2,2,2-trichloro-ethoxycarbonylamino)-propyl]-piperidine-1-carboxylic acid tert-butyl ester → (2-oxo-1-piperidin-4-ylmethyl-2-thiazol-2-yl-ethyl)-carbamic acid 2,2,2-trichloro-ethyl ester; compound with toluene-4-sulfonic acid

Conditions	Yield
In diethyl ether at 35℃; for 2h;	100%

L-cystine (56-89-3) + toluene-4-sulfonic acid (104-15-4) + allyl alcohol (107-18-6) → L-cystine-bis-allyl ester bis-(toluene-4-sulfonate)

Conditions	Yield
In benzene at 90℃; for 16h;	100%
In benzene for 12h; Esterification; Heating;	95%

11-aminoundecanoic acid (2432-99-7) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6) → 11-Aminoundecanoic acid benzyl ester p-toluenesulfonate

Conditions	Yield
In toluene for 5h; Inert atmosphere; Heating;	100%
In benzene for 24h; Reflux;	96%
In benzene Esterification;

D-Threonine (632-20-2) + toluene-4-sulfonic acid (104-15-4) + allyl alcohol (107-18-6) → H-D-Thr-Oallyl p-tolunenesulfonate

Conditions	Yield
In toluene at 140℃; for 24h; Dean-Stark; Schlenk technique; Inert atmosphere;	100%
In benzene for 42h; Heating;

toluene-4-sulfonic acid (104-15-4) + 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 (322407-87-4) → 2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-[(O-t-butylcarbonyl)tyrosylamino]acetic acid n-butyl ester p-toluenesulfonate salt

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 2h;	100%

toluene-4-sulfonic acid (104-15-4) + {tert-butoxycarbonylmethyl-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-amino}-acetic acid tert-butyl ester (207612-91-7) → {carboxymethyl-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-amino}-acetic acid; compound with toluene-4-sulfonic acid

Conditions	Yield
In dichloromethane for 24h;	100%

toluene-4-sulfonic acid (104-15-4) + {tert-butoxycarbonylmethyl-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-hexyl]-amino}-acetic acid tert-butyl ester (445390-52-3) → {carboxymethyl-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-hexyl]-amino}-acetic acid; compound with toluene-4-sulfonic acid

Conditions	Yield
In dichloromethane for 24h;	100%

toluene-4-sulfonic acid (104-15-4) + {tert-butoxycarbonylmethyl-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-amino}-acetic acid tert-butyl ester (207612-91-7) → {carboxymethyl-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-amino}-acetic acid; compound with toluene-4-sulfonic acid

Conditions	Yield
In dichloromethane	100%

Upstream product

• 67-56-1 Methanol 
• 98-59-9 Tosyl chloride 

Downstream Products

• 20592-42-1 estra-1,3,5(10),16-tetraene-3,17-diol diacetate 
• 40753-13-7 4-(4-BROMOPHENYL)-1,2,3-THIADIAZOLE 
• 107868-30-4 Exemestane 
• 64485-82-1 Ethyl 2-(2-aminothiazole-4-yl)-2-hydroxyiminoacetate 
• 2981-10-4 1-(1-PIPERIDINO)CYCLOHEXENE 
• 126318-27-2 3-NITROBENZO[B]FURAN-5-OL 
• 83647-97-6 Spirapril 
• 88-53-9 2-Amino-5-chloro-4-methylbenzenesulfonic acid 
• 112055-34-2 ETHYL 2-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE 
• 98534-81-7 1-PHENYL-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID 
• 112-47-0 1,10-Decanediol 
• 30766-22-4 Methyl 5-hydroxynicotinate 
• 626-82-4 Butyl hexanoate 
• 22356-80-5 2-hydroxy-4-methylbenzenesulphonic acid 
• 540-07-8 PENTYL HEXANOATE 
• 7753-60-8 ANECORTAVE ACETATE (200 MG)F0E2980.997MG/MG(AI) 
• 590-01-2 Butyl propionate 
• 638-25-5 FEMA 2079 
• 69975-86-6 Doxofylline 
• 321309-26-6 5-METHYL-4-ISOXAZOLESULFONYL CHLORIDE 
• 638-11-9 ISOPROPYL BUTYRATE 
• 51-68-3 2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate 
• 999-21-3 DIALLYL MALEATE 
• 2478-10-6 4-Hydroxybutyl acrylate 
• 2408-20-0 ALLYL PROPIONATE 
• 4249-10-9 1,2,3,4-TETRAMETHYL-1,3-CYCLOPENTADIENE 
• 90035-08-8 Flocoumafen 
• 637-78-5 ISOPROPYL PROPIONATE 
• 626-77-7 Caproic acid propyl ester 
• 194490-18-1 5-TERT-BUTYL-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER 
• 2035-99-6 FEMA 2080 
• 852691-03-3 ETHYL 1-(TERT-BUTYL)-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE 

Recommend Products

• 101169-52-2  toluene-4-sulfonic acid 2-oxo-3-phenyl-propyl ester 
• 186581-53-3  diazomethane 
• 103-80-0  phenylacetyl chloride 
• 15051-88-4  trans-cyclopentane-1,2-diol 1-tosylate 
• 285-67-6  Cyclopentene oxide 
• 7716-07-6  (13S)-10-hydroxy-5β,10α-ros-15-en-18-oic acid-lactone 
• 123-91-1  1,4-dioxane 
• 5835-26-7  isopimaric acid 
• 39794-75-7  ethyl α-p-toluenesulfonyloxyacetate 
• 503-68-4  diazoacetic acid 
• 854840-12-3  3,4-Epoxy-2,2,5,5-tetramethyl-tetrahydro-furan 
• 98-88-4  benzoyl chloride 
• 817-95-8  ethyl 2-ethoxyethanoate 
• 623-73-4  diazoacetic acid ethyl ester