599-91-7

Basic information

• Product Name: PROPYL P-TOLUENESULFONATE
• Synonyms: 4-METHYLBENZENESULFONIC ACID, PROPYL ESTER;N-PROPYLTOSYLATE;N-PROPYL P-TOLUENESULFONATE;P-TOLUENESULFONIC ACID N-PROPYL ESTER;P-TOLUENESULFONIC ACID PROPYL ESTER;PROPYL P-TOLUENESULFONATE;PROPYL P-TOSYLATE;4-methyl-benzenesulfonicacipropylester
• CAS NO: 599-91-7
• Molecular Formula: C₁₀H₁₄O₃S
• Molecular Weight: 214.28
• EINECS: 209-978-5
• Mol File: 599-91-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: <-20 °C
• Boiling Point: 140 °C (2 mmHg)
• Flash Point: 147.8°C
• Appearance: Clear light yellow/Liquid
• Density: 1.15
• Vapor Pressure: 0.000583mmHg at 25°C
• Refractive Index: 1.5065-1.5085
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: PROPYL P-TOLUENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: PROPYL P-TOLUENESULFONATE(599-91-7)
• EPA Substance Registry System: PROPYL P-TOLUENESULFONATE(599-91-7)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• Hazardous Substances Data: 599-91-7(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow liquid

Uses

Propyl 4-Toluenesulfonate is used as a catalyst for epoxy resins and amine compositions. Propyl 4-Toluenesulfonate is also used in soldering of electronic parts.

InChI:InChI=1/C10H14O3S/c1-3-8-13-14(11,12)10-6-4-9(2)5-7-10/h4-7H,3,8H2,1-2H3

Synthetic route

toluene-4-sulfonic acid (104-15-4) + propyloxy(diphenyl)-λ6-sulfanenitrile (143885-02-3) → S,S-diphenylsulphoximine (22731-83-5) + propyl tosylate (599-91-7)

Conditions	Yield
In chloroform-d1 at 20℃; for 1h;	A n/a B 98%

propan-1-ol (71-23-8) + p-toluenesulfonyl chloride (98-59-9) → propyl tosylate (599-91-7)

Conditions	Yield
With pyridine at 0℃; for 3h;	96%
With triethylamine In dichloromethane at 5 - 22℃; for 12.5h; Industry scale;	95%
With triethylamine In dichloromethane at 5 - 22℃; for 12.5h; Industry scale;	95%

propan-1-ol (71-23-8) + toluene-4-sulfonic acid (104-15-4) → propyl tosylate (599-91-7)

Conditions	Yield
Stage #1: toluene-4-sulfonic acid With potassium phosphate monohydrate; bis(trichloromethyl) carbonate In dichloromethane at 0 - 5℃; for 0.0833333h; Stage #2: With triethylamine In dichloromethane at 20℃; for 0.333333h; Stage #3: propan-1-ol With trimethylamine hydrochloride In dichloromethane at 20℃; for 0.5h;	90%

propan-1-ol (71-23-8) + sodium 4-methylbenzenesulfinate (824-79-3) → propyl tosylate (599-91-7)

Conditions	Yield
With iodine; sodium methylate In acetonitrile at 20℃; for 5h; Green chemistry;	63%

tri-n-propyl phosphite (923-99-9) + toluene-4-sulfonic acid (104-15-4) → propyl tosylate (599-91-7)

Conditions	Yield
In 1,2-dichloro-ethane; toluene for 24h; Heating;	52%
In 1,2-dichloro-ethane for 24h; Product distribution; Heating; investigate effect of solvent and reaction time;	52%

propan-1-ol (71-23-8) + 4-methylbenzenediazonium tetrafluoroborate (459-44-9) → propyl tosylate (599-91-7)

Conditions	Yield
With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; trifluoroacetic acid; copper(ll) bromide In dichloromethane at 20℃; for 12h;	41%

phosphoric acid tripropyl ester (513-08-6) + toluene-4-sulfonic acid (104-15-4) → propyl tosylate (599-91-7)

Conditions	Yield
In toluene for 9h; Heating;	39%
In toluene for 9h; Product distribution; Heating; investigate effect of solvent and reaction time;	39%

propan-1-ol (71-23-8) + p-toluenesulfonyl chloride (98-59-9) → Dipropyl ether (111-43-3) + propyl tosylate (599-91-7)

Conditions	Yield
at 117℃; unter Durchleiten von Luft;

Dipropyl ether (111-43-3) + acetyl p-toluenesulfonate (26908-82-7) → propyl tosylate (599-91-7)

dipropyl propylphosphonate (1789-95-3) + methyl p-toluene sulfonate (80-48-8) → propanephosphonic acid dimethyl ester (18755-43-6) + Methyl propyl propylphosphonate (18755-44-7) + propyl tosylate (599-91-7)

Conditions	Yield
at 130 - 140℃; for 3.5h;

toluene (108-88-3) → propyl tosylate (599-91-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium chloride; chlorosulfonic acid / -0.16 °C 2: 39.84 °C View Scheme

propyl tosylate (599-91-7) + triphenylphosphine (603-35-0) → triphenyl(propyl)phosphonium 4-methylbenzenesulfonate (101610-04-2)

Conditions	Yield
	94%
In Petroleum ether

4-benzyloxy-1-phenethyl alcohol + propyl tosylate (599-91-7) → 1-(benzyloxy)-4-(2-propoxyethyl)benzene

Conditions	Yield
In N-methyl-acetamide	94%

propyl tosylate (599-91-7) → dipropyltrithiocarbonate (2314-50-3)

Conditions	Yield
With carbon disulfide; caesium carbonate In dimethyl sulfoxide at 20 - 25℃; for 4h; Inert atmosphere;	94%

propyl tosylate (599-91-7) → Dipropyl disulfide (629-19-6)

Conditions	Yield
With sodium carbonate; sulfur; thiourea In water at 70℃; for 6h; Green chemistry;	91%

1-Heptyne (628-71-7) + propyl tosylate (599-91-7) → 4-pentyl-1-propyl-1H-1,2,3-triazole

Conditions	Yield
With sodium azide In water at 20℃; for 3.5h; Huisgen Cycloaddition; Green chemistry;	91%

methyl 4-(1-hydroxy ethyl)benzoate (84851-56-9) + propyl tosylate (599-91-7) → (+)-methyl 4-(1-propoxyethyl)benzoate

Conditions	Yield
In N-methyl-acetamide	90%

(15β,16α)-16-hydroxy-15-(hydroxymethyl)beyeran-18-oic acid (882175-40-8) + propyl tosylate (599-91-7) → n-propyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate (1143505-97-8)

Conditions	Yield
With potassium carbonate In acetonitrile	90%

propyl tosylate (599-91-7) + (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-diamine (106092-09-5) → 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole p-toluenesulfonic acid (943319-02-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 76℃; for 6h; Reagent/catalyst; Solvent; Temperature;	88.2%
In N,N-dimethyl-formamide at 20℃; for 96h;	64%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	54%

5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene (157432-87-6, 288302-11-4, 288302-12-5) + propyl tosylate (599-91-7) → 25,27-dipropoxy-26,28-dihydroxy-p-t-butylcalix[4]arene (137693-26-6)

Conditions	Yield
With potassium carbonate In n-C3H7CN for 40h; Reflux;	88%
With potassium carbonate for 40h; Reflux;	88%

5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene (157432-87-6, 288302-11-4, 288302-12-5) + propyl tosylate (599-91-7) → 5,11,17,23-tetra-tert-butyl-25,26-dihydroxy-27,28-dipropoxy-calix<4>arene (308796-39-6)

Conditions	Yield
With sodium hydroxide In water; dimethyl sulfoxide at 50 - 70℃; for 24h;	88%

(5-Hydroxy-9-oxo-9H-xanthen-4-yl)-acetic acid (117570-63-5) + propyl tosylate (599-91-7) → (9-Oxo-5-propoxy-9H-xanthen-4-yl)-acetic acid (126157-97-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 80℃; for 2h;	86%

7-hydroxy-4-methyl-indan-1-one (67901-82-0) + propyl tosylate (599-91-7) → 4-methyl-7-propoxyindan-1-one (94102-82-6)

Conditions	Yield
With potassium carbonate In acetone Heating;	85%

2-(4-chloro-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane (827605-29-8) + propyl tosylate (599-91-7) → 1-chloro-4-propylbenzene (52944-34-0)

Conditions	Yield
With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 60℃; for 12h; Suzuki-Miyauri coupling; Inert atmosphere;	84%

5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane (5123-13-7) + propyl tosylate (599-91-7) → Propylbenzene (103-65-1)

Conditions	Yield
With copper(l) iodide; cyclohexa-1,4-diene; lithium tert-butoxide In N,N-dimethyl-formamide at 60℃; for 12h; Suzuki-Miyauri coupling; Inert atmosphere;	84%

propyl tosylate (599-91-7) + (R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine (106092-11-9) → (R)-(+)-2-amino-4,5,6,7-tetrahydro-6-(n-propylamino)benzothiazole p-toluenesulfonic acid (1332723-78-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20 - 80℃; Solvent; Inert atmosphere;	83.9%

C18H17NO3S + propyl tosylate (599-91-7) → Imrecoxib (395683-14-4)

Conditions	Yield
Stage #1: C18H17NO3S With sodium amide In toluene for 1h; Reflux; Stage #2: propyl tosylate In toluene at 20 - 100℃; for 12h;	83.6%

25,26,27,28-tetrakis(hydroxy)calix[4]arene (248590-47-8) + propyl tosylate (599-91-7) → 25,26,27,28-tetrapropyloxycalix[4]arene (140862-52-8, 140924-91-0, 141902-33-2, 143444-60-4, 147782-22-7)

Conditions	Yield
Stage #1: 25,26,27,28-tetrakis(hydroxy)calix[4]arene With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Stage #2: propyl tosylate In N,N-dimethyl-formamide at 80℃; for 7h;	82%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 7h; Yields of byproduct given;
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 7h; Yield given. Title compound not separated from byproducts;

6-methylbenzothiazol-2-ylamine (2536-91-6) + propyl tosylate (599-91-7) → C11H15N2S(1+)

Conditions	Yield
at 120℃; for 3h; Sealed tube;	76.3%

2-(3,4-dimethoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane (1177398-99-0) + propyl tosylate (599-91-7) → 4-propyl-1,2-dimethoxybenzene (5888-52-8)

Conditions	Yield
With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 60℃; for 12h; Suzuki-Miyauri coupling; Inert atmosphere;	76%

ethyl 4'-(1-hydroxyethyl)-4-biphenylcarboxylate (123023-78-9, 119838-64-1) + propyl tosylate (599-91-7) → (+)-ethyl 4'-(1-propoxyethyl)-4-biphenylcarboxylate (119838-65-2)

Conditions	Yield
In N-methyl-acetamide	75%

(3S,4R)-4-((S)-1-((4-methoxy-benzyl)oxy)ethyl)-7-methyloct-1-en-3-ol + propyl tosylate (599-91-7) → 1-methoxy-4-((((2S,3S)-6-methyl-3-((S)-1-propoxyallyl)heptan-2-yl)oxy)methyl)benzene

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 72h;	74%
With potassium tert-butylate In tetrahydrofuran at 20℃; for 72h;	74%

4-methoxyphenylboronic acid (5720-07-0) + propyl tosylate (599-91-7) → 1-methoxy-4-(propylsulfonyl)benzene (1491216-03-5)

Conditions	Yield
Stage #1: 4-methoxyphenylboronic acid With dichloro bis(acetonitrile) palladium(II); potassium pyrosulfite; tetrabutylammomium bromide; tert-butyl XPhos In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: propyl tosylate In N,N-dimethyl-formamide at 85℃; for 22h; Inert atmosphere; Sealed tube;	74%

propyl tosylate (599-91-7) + p-tert-butylcalix<4>arene (150990-01-5) → 5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-dihydroxy-26,28-di(1-propoxy)calix[4]arene

Conditions	Yield
With potassium carbonate for 40h; Reflux;	71%

(1R,3S)-[2-(trimethylsilyl)ethyl] 3-amino-1,2,2-trimethylcyclopentanecarboxylate (1304668-85-6) + propyl tosylate (599-91-7) → C17H35NO2Si (1304668-88-9)

Conditions	Yield
Stage #1: (1R,3S)-[2-(trimethylsilyl)ethyl] 3-amino-1,2,2-trimethylcyclopentanecarboxylate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: propyl tosylate In N,N-dimethyl-formamide at 20℃; for 24h;	70%

(S)-10-(4-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-9-fluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4] oxazino[2,3,4-ij]quinoline-6-carboxylic acid + propyl tosylate (599-91-7) → (S)-10-(4-(1-propyl-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-9-fluoro-3-methyl-7-oxo-3,5,6,7-tetrahydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

Conditions	Yield
With triethylamine adsorbed alumina In neat (no solvent) at 100℃; for 0.05h; Sealed tube; Microwave irradiation;	69.7%

2-(2'-bromophenyl)-1H-indole (88207-45-8) + propyl tosylate (599-91-7) → 2-(2-bromophenyl)-1-n-propyl-1H-indole

Conditions	Yield
Stage #1: 2-(2'-bromophenyl)-1H-indole With potassium hydroxide In N,N-dimethyl-formamide Stage #2: propyl tosylate In N,N-dimethyl-formamide at 20℃; for 24h;	69%

Upstream product

• 71-23-8 propan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 104-15-4 toluene-4-sulfonic acid 
• 143885-02-3 propyloxy(diphenyl)-λ⁶-sulfanenitrile 
• 108-88-3 toluene 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 513-08-6 phosphoric acid tripropyl ester 
• 923-99-9 tri-n-propyl phosphite 
• 1789-95-3 dipropyl propylphosphonate 
• 80-48-8 methyl p-toluene sulfonate 
• 111-43-3 Dipropyl ether 
• 26908-82-7 acetyl p-toluenesulfonate 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 109499-07-2 3-hydroxy-1-propyl-pyridinium; toluene-4-sulfonate 
• 854256-33-0 1-methyl-4-nitro-2-n-propoxybenzene 
• 16169-28-1 4-methoxy-2-nitro-1-propoxy-benzene 
• 943598-89-8 4t-(3-methoxy-4-propoxy-phenyl)-but-3-en-2-one 
• 875846-16-5 3-propyloxy-4-nitrobenzoic acid 
• 35288-44-9 3-nitro-4-propoxybenzoic acid 
• 103204-41-7 4-nitro-2-propoxy-benzoic acid 
• 1071638-29-3 4-nitro-2-propoxy-benzoic acid methyl ester 
• 2307-10-0 S-propyl thiol-acetate 
• 45815-08-5 2-(propylamino)pyridine 
• 50616-07-4 N,N-dipropylpyridin-2-amine 
• 3898-41-7 1,4-dipropoxybenzene 
• 622-85-5 propoxybenzene 
• 540-54-5 1-Chloropropane 

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