6192-52-5

Basic information

• Product Name: p-Toluenesulfonic acid monohydrate
• Synonyms: 4-Methylbenzenesulfonic acid hydrate;Lisinopril EP IMpurity B;p-Toluenesulfonic Acid, Monohydrate, ACS;Benzenesulfonic acid,4-Methyl-, hydrate (1:1);P-toluene sulfonic acid(water;p-Toluenesulfonic acid Monohydrate >=98.0% (T), >=98.0% (HPLC);p-Toluenesulfonic acid monohydrate;p-Toluenesulfonic acid monohydrate ACS reagent, >=98.5%
• CAS NO: 6192-52-5
• Molecular Formula: C₇H₈O₃S*H₂O
• Molecular Weight: 190.22
• EINECS: 203-180-0
• Product Categories: fine chemical;Pharmaceutical intermediates;Sulphur Derivatives;Reagent Grade;Organic AcidsOrganic Building Blocks;Organic AcidsDerivatization Reagents TLC;Chemical Synthesis;Synthetic Reagents;TLC Reagents, S-Z;TLC Visualization Reagents (alphabetic sort);Organic Building Blocks;Sulfonic/Sulfinic Acids;Sulfur Compounds;Organic Acids;ACS GradeChemical Synthesis;Essential Chemicals;Routine Reagents
• Mol File: 6192-52-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 96-99 °C(lit.)
• Boiling Point: 140°C 20mm
• Flash Point: 180 °C
• Appearance: White to pink/Solid
• Density: 1,24 g/cm3
• Vapor Density: 5.9 (vs air)
• Vapor Pressure: 4.06E-08mmHg at 25°C
• Refractive Index: 1,382-1,384
• Storage Temp.: Store at RT.
• Solubility: H2O: 0.1 g/mL, clear
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases, most common metals. Protect from moisture.
• Merck: 14,9533
• BRN: 3568023
• CAS DataBase Reference: p-Toluenesulfonic acid monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: p-Toluenesulfonic acid monohydrate(6192-52-5)
• EPA Substance Registry System: p-Toluenesulfonic acid monohydrate(6192-52-5)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34-37
• Safety Statements: 26-37-45-36/37/39
• RIDADR: UN 2585 8/PG 3
• RTECS: XT6300000
• F: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6192-52-5(Hazardous Substances Data)

Usage

Chemical Description

P-toluenesulfonic acid monohydrate is a white crystalline powder, and the dimethyl acetals are colorless liquids.

Chemical Properties

White crystals

Uses

Different sources of media describe the Uses of 6192-52-5 differently. You can refer to the following data:
1. Derivitizing agent.
2. p-Toluenesulfonic acid monohydrate is used as a catalyst in the synthesis of resveratrol, in oxane derivatives as an antimalarial agent, as substituted piperidine and unsymmetrical benzyl. It acts as a catalyst in the preparation of 1,3,5-trisubstituted pyrazoles derivatives, selenated ketene dithioacetals, triazoloquinazolinone and benzimidazoquinazolinone derivatives. It also serves as an intermediate in the esterification and in reductive amination reactions.
3. p-Toluenesulfonic acid monohydrate (p-TsOH·H2O) may be used as a catalyst in the synthesis of the following:Unsymmetrical benzils.Highly substituted piperidines.1,3,5-Trisubstituted benzenes by trimerization of alkynes.Triazoloquinazolinone and benzimidazoquinazolinone derivatives.1,3,5-Trisubstituted pyrazoles derivatives.Selenated ketene dithioacetals.

General Description

p-Toluenesulfonic acid monohydrate, an oxonium salt, is an inexpensive and easy to handle organic catalyst used in organic synthesis. The study of its crystalline structure shows that it is monoclinic with P21/c space group. Its solubility in aqueous sulfuric acid solutions has been studied.

Purification Methods

Purify the acid by precipitation from a saturated solution at 0o by introducing HCl gas. It can also be crystallised from conc HCl, then crystallised from dilute HCl (charcoal) to remove benzenesulfonic acid. It has been crystallised from EtOH/water. Dry it in a vacuum desiccator over solid KOH and CaCl2. p-Toluenesulfonic acid can be dehydrated by azeotropic distillation with *benzene or by heating at 100o for 4hours under water-pump vacuum. The anhydrous acid can be crystallised from *benzene, CHCl3, ethyl acetate, anhydrous MeOH, or from acetone by adding a large excess of *benzene. It can also be dried under vacuum at 50o. The S-benzylisothiuronium salt has m 182o (from aqueous EtOH). [Beilstein 11 IV 241.]

InChI:InChI=1/C7H8O3S.H2O/c1-6-2-4-7(5-3-6)11(8,9)10;/h2-5H,1H3,(H,8,9,10);1H2

Synthetic route

(η5-C5H5)OsH(PPh3)2 + p-toluenesulfonic acid monohydrate (6192-52-5) → dihydrido(η-cyclopentadienyl)bis(triphenylphosphine)osmium(IV)(p-toluenesulphonate) (112246-30-7)

Conditions	Yield
In methanol mixture heated for 2 min at 40°C; evaporated, washed with water, decanted, dried;	100%

1,1,1-trioctyl-1-methylphosphonium methylcarbonate (1204316-79-9) + p-toluenesulfonic acid monohydrate (6192-52-5) → tri-n-octyl(methyl)phosphonium tosylate (1204316-80-2)

Conditions	Yield
In methanol at 40℃; for 1h;	100%

tri-n-butyl(methyl)phosphonium methyl carbonate (120256-45-3) + p-toluenesulfonic acid monohydrate (6192-52-5) → tributyl(methyl)phosphonium 4-methylbenzenesulfonate (55767-12-9)

Conditions	Yield
In methanol at 40℃; for 1h;	100%

tri-n-hexyl(methyl)phosphonium methyl carbonate (1258887-13-6) + p-toluenesulfonic acid monohydrate (6192-52-5) → tri-n-hexyl(methyl)phosphonium tosylate (1258887-11-4)

Conditions	Yield
In methanol at 40℃; for 1h;	100%

4-(trans-[1,1'-bi(cyclohexane)]-4-yl)aniline + p-toluenesulfonic acid monohydrate (6192-52-5) → C18H27N*C7H8O3S

Conditions	Yield
In methanol at 20℃; for 2.5h;	100%

C25H30Co3MnN3O14 + p-toluenesulfonic acid monohydrate (6192-52-5) → C30H34Co3MnN3O15S

Conditions	Yield
In dichloromethane for 16h;	100%

1-(4-iodobenzyl)-3-methylimidazolium tetrafluoroborate + p-toluenesulfonic acid monohydrate (6192-52-5) → 1-[4-hydroxyl(tosyloxy)-iodobenzyl]-3-methylimidazolium tetrafluoroborate

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In acetonitrile at 30℃; for 0.5h; Inert atmosphere;	99.1%

p-toluenesulfonic acid monohydrate (6192-52-5) + N-Boc O-tosyl L-homoserine benzyl ester (116393-76-1) → O-benzenesulphonyl benzyl L-homoserine tosylate (116393-81-8)

Conditions	Yield
In ethanol	99%

p-toluenesulfonic acid monohydrate (6192-52-5) + palladium diacetate (3375-31-3) + Acetanilid (103-84-4) → [(acetanilide(-1H))Pd(p-toluene sulfonato)]2

Conditions	Yield
In dioxane heated at 40°C for 10 min; filtered, dried (vac.);	99%
In CH2Cl2 heated at 40°C for 1 min; filtered, dried (vac.);	99%

1-(4-methoxyphenyl)-1-cyclopropanecarboxylic acid (16728-01-1) + p-toluenesulfonic acid monohydrate (6192-52-5) → 1-(4-methoxyphenyl)cyclopropanecarboxylic acid methyl ester (779206-51-8)

Conditions	Yield
In methanol; ethyl acetate	99%
In methanol; ethyl acetate	99%
In methanol; ethyl acetate	99%

p-toluenesulfonic acid monohydrate (6192-52-5) + 3-benzylthiazolium bromide (75066-50-1) → 3-benzylthiazolium paratoluenesulfonate

Conditions	Yield
In water at 20℃; for 4h; Inert atmosphere;	99%

1-[4-(diacetoxyiodo)benzyl]-3-methylimidazolium tetrafluoroborate + p-toluenesulfonic acid monohydrate (6192-52-5) → 1-[4-hydroxyl(tosyloxy)-iodobenzyl]-3-methylimidazolium tetrafluoroborate

Conditions	Yield
for 0.166667h;	98.9%

[bis(acetoxy)iodo]benzene (3240-34-4) + p-toluenesulfonic acid monohydrate (6192-52-5) → [hydroxy(tosyloxy)iodo]benzene (27126-76-7)

Conditions	Yield
for 0.00555556h; Microwave irradiation; neat (no solvent);	98%

Methyl 3-formylbenzoate (52178-50-4) + p-toluenesulfonic acid monohydrate (6192-52-5) → 3-[1,3]Dioxolan-2-yl-benzoic acid methyl ester (124038-36-4)

Conditions	Yield
In ethylene glycol; toluene	98%

(S)-N-benzyloxycarbonylaspargine t-butyl ester (25456-85-3) + p-toluenesulfonic acid monohydrate (6192-52-5) → (S)-2-Amino-succinamic acid tert-butyl ester; compound with toluene-4-sulfonic acid (4124-53-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 18h;	97%

p-toluenesulfonic acid monohydrate (6192-52-5) + Z-Gly-Phe-Phe-Tyr(But)-AlaOPh (86095-66-1) → (S)-2-[(S)-2-{(S)-2-[(S)-2-(2-Amino-acetylamino)-3-phenyl-propionylamino]-3-phenyl-propionylamino}-3-(4-tert-butoxy-phenyl)-propionylamino]-propionic acid phenyl ester; compound with toluene-4-sulfonic acid (86096-07-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide for 18h;	97%

4-chloro-1-(diacetoxyiodo)benzene (6973-73-5) + p-toluenesulfonic acid monohydrate (6192-52-5) → -p-chlorobenzene (73178-07-1)

Conditions	Yield
for 0.00555556h; Microwave irradiation; neat (no solvent);	97%

[((Me)Cp)2MoH2] (61112-91-2) + p-toluenesulfonic acid monohydrate (6192-52-5) → 2C5H4CH3(1-)*Mo(4+)*2O3SC6H4CH3(1-)=(C5H4CH3)2Mo(O3SC6H4CH3)2

Conditions	Yield
With acetone In acetone byproducts: 2-propanol; vac.; stirring (room temp., 14 h); removal of volatilies, washing (Et2O), recrystn. (acetone); elem. anal.;	96.2%

p-toluenesulfonic acid monohydrate (6192-52-5) + [1-(3-Fluoro-phenyl)-1-hydroxy-2-nitro-ethyl]-phosphonic acid dimethyl ester (138479-41-1) → [2-Amino-1-(3-fluoro-phenyl)-1-hydroxy-ethyl]-phosphonic acid dimethyl ester; compound with toluene-4-sulfonic acid (138479-34-2)

Conditions	Yield
With hydrogen; nickel In ethanol at 20 - 25℃; under 760 Torr;	96%

mer,trans-Re(CO)3(PPh3)2CHO (118228-22-1) + p-toluenesulfonic acid monohydrate (6192-52-5) → mer,trans-{Re(CO)3(PPh3)2(CHOH)}(p-MeC6H4SO3)

Conditions	Yield
In diethyl ether; dichloromethane N2 atmosphere; addn. of Re-complex to sulfonic acid in CH2Cl2/ether mixt. 3:1 (small portions, room temp.), stirring (5 min); cooling (0°C), pptn. on pentane addn. (stirring), filtration off; elem. anal.;	96%

p-toluenesulfonic acid monohydrate (6192-52-5) + N-Boc O-tosyl L-homoserine benzyl ester (116393-76-1) → O-tosyl L-homoserine benzyl ester tosylate (116393-79-4)

Conditions	Yield
In ethanol	95%

3,4-dihydro-2H-pyran (110-87-2) + 3-hydroxy-octanenitrile (64250-18-6) + p-toluenesulfonic acid monohydrate (6192-52-5) → 3-(tetrahydro-2H-pyran-2-yloxy)caprylonitrile

Conditions	Yield
	95%

(C(CH2CH2P(C(CH3)3)2)2CH2RhCH3) (189168-25-0) + p-toluenesulfonic acid monohydrate (6192-52-5) → (C(CH2CH2P(C(CH3)3)2)2CH2RhOSO2C6H4CH3) (284041-45-8)

Conditions	Yield
In tetrahydrofuran to soln. (H2CC(CH2CH2P(But)2)2RhMe) in THF HOTs*H2O was added; solvent was evapd., solid was washed with pentane;	95%

4Pd(2+)*4CH3COO(1-)*2C6H2(C7H4N2(C2H5))2(2-)=[Pd2(CH3COO)2(C6H2(C7H4N2(C2H5))2)]2 + p-toluenesulfonic acid monohydrate (6192-52-5) → 2Pd(2+)*2CH3C6H4SO3(1-)*C6H2(C7H4N2(C2H5))2(2-)*2(CH3)2SO=Pd2(CH3C6H4SO3)2(C6H2(C7H4N2(C2H5))2)((CH3)2SO)2

Conditions	Yield
In dimethyl sulfoxide addn. of Pd-complex to 2 equiv. of tosyl acid; pptn. on slow diffusion of ether into soln.; elem. anal.;	95%

dichloromethane (75-09-2) + [Pd(κ2-N,C-2-phenylquinoline)(OAc)] (1145982-29-1, 765298-83-7, 766551-17-1) + p-toluenesulfonic acid monohydrate (6192-52-5) + triphenylphosphine (603-35-0) → [Pd(κ2-N,C-2-phenylquinoline)(triphenylphosphine)(p-toluenesulfonato)]*CH2Cl2 (1144030-76-1)

Conditions	Yield
In chloroform stirring of mixt. of (Pd(OAc)(2-phenylquinoline))2, PPh3 and p-toluenesulfonic acid in CHCl3 at room temp. for 15 min; filtration, addn. of hexanes; pptn., filtration, recrystn. from ether CH2Cl2/hexane or CHCl3/hexane; elem. anal.;	95%

2-(diacetoxyiodo)toluene (31599-59-4) + p-toluenesulfonic acid monohydrate (6192-52-5) → -o-toluene (73177-97-6)

Conditions	Yield
for 0.00555556h; Microwave irradiation; neat (no solvent);	95%

2-methylcyclohexane-1,3-dione (1193-55-1) + p-toluenesulfonic acid monohydrate (6192-52-5) + 2-bromoaniline (615-36-1) → (E)-2-bromo-N-(3-((2-bromophenyl)amino)-2-methylcyclohex-2-en-1-ylidene)benzenaminium 4-methylbenzenesulfonate

Conditions	Yield
In toluene for 48h; Reflux;	95%

2-methylcyclohexane-1,3-dione (1193-55-1) + p-toluenesulfonic acid monohydrate (6192-52-5) + 4-methoxy-aniline (104-94-9) → (E)-4-methoxy-N-(3-((4-methoxyphenyl)amino)-2-methylcyclohex-2-en-1-ylidene)benzenaminium 4-methylbenzenesulfonate

Conditions	Yield
In toluene for 48h; Reflux;	95%

Methyl 5,8-dimethoxy-1-hydroxyisochroman-3-yl ketone (187597-81-5) + p-toluenesulfonic acid monohydrate (6192-52-5) → 1-hydroxyisochroman (95033-78-6)

Conditions	Yield
With triethylamine In water; acetone	94%

p-toluenesulfonic acid monohydrate (6192-52-5) + 2,2-dimethoxy-propane (77-76-9) + 6-deoxypenciclovir (104227-86-3) → 5-[2-(2-aminopurin-9-yl)ethyl]-2,2-dimethyl-1,3-dioxane (104227-89-6)

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide	94%

Downstream Products

• 1738-72-3 L-serine benzyl ester 
• 5184-64-5 1,3,5-trimethyl-2-(toluene-4-sulfonyl)-benzene 
• 42772-85-0 2-hydroxyethyl 4-methylbenzenesulfonate 
• 778-28-9 butyl para-toluenesulfonate 
• 3839-35-8 4-methylbenzenesulfonic acid n-hexylester 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 90472-86-9 benzyl D,L-α-aminoxy-phenylacetate p-toluenesulphonate 
• 90472-84-7 benzyl-D-2-aminoxy-3-phenylpropionate p-toluenesulphonate 
• 227290-59-7 (R)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid benzyl ester; compound with toluene-4-sulfonic acid 
• 77497-97-3 benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt 
• 222634-40-4 ethyl 2-(1-(1,3-diethoxy-2-propoxycarbonyloxy)-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate 
• 222633-77-4 ethyl 5-(3,4-dimethoxybenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylate 
• 104675-23-2 N-(3-oxocyclohexen-1-yl)-2-aminobenzonitrile 
• 142329-84-8 4-nitrophenyl O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->6)-2,3-O-isopropylidene-α-D-mannopyranoside