2307-69-9

Basic information

• Product Name: ISOPROPYL P-TOLUENESULFONATE
• Synonyms: ISOPROPYL P-TOLUENESULFONATE;ISOPROPYL 4-TOLUENESULPHONATE;isopropyl toluene-4-sulphonate;ISOPROPYLPARA-TOLUENESULPHONATE;ISOBUTYL 4-METHYLBENZENESULFONATE;4-Methylbenzenesulfonic acid 1-methylethyl ester;p-Toluenesulfonic acid isopropyl ester;(4-methylphenyl) propane-2-sulfonate
• CAS NO: 2307-69-9
• Molecular Formula: C₁₀H₁₄O₃S
• Molecular Weight: 214.28
• EINECS: 218-989-4
• Mol File: 2307-69-9.mol
• Article Data: 26

Chemical Properties

• Melting Point: 20
• Boiling Point: 314.1 °C at 760 mmHg
• Flash Point: 110
• Appearance: /
• Density: 1.142 g/mL at 25 °C
• Vapor Pressure: 0.00088mmHg at 25°C
• Refractive Index: n20/D1.503
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: ISOPROPYL P-TOLUENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPROPYL P-TOLUENESULFONATE(2307-69-9)
• EPA Substance Registry System: ISOPROPYL P-TOLUENESULFONATE(2307-69-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 2307-69-9(Hazardous Substances Data)

Usage

Uses

Isopropyl p-Tosylate is a sulfonic acid ester, a potentialy alkylating agent. Studies suggest Isopropyl p-Tosylate may exert genotoxic effects in bacterial and mammalian cell systems.

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

Synthetic route

toluene-4-sulfonic acid (104-15-4) + isopropyloxy(diphenyl)-λ6-sulfanenitrile (143885-03-4) → toluene-4-sulfonic acid isopropyl ester (2307-69-9) + S,S-diphenylsulphoximine (22731-83-5)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.25h;	A 99% B n/a

p-toluenesulfonyl chloride (98-59-9) + isopropyl alcohol (67-63-0) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
With pyridine at 0℃; for 3h;	94%
With potassium hydroxide; potassium carbonate for 0.05h;	90%
With pyridine at 0 - 20℃;	85%

2-iodo-propane (75-30-9) + [hydroxy(tosyloxy)iodo]benzene (27126-76-7) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
In chloroform at 25℃; for 1h; further solvent;	90%

toluene-4-sulfonic acid (104-15-4) + isopropyl alcohol (67-63-0) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
With (fluoro)diphenyl-η6-sulfanenitrile; sodium at 20℃; for 0.333333h;	88%
Fe(3+)-exchanged montmorillonite clay In 1,2-dichloro-ethane at 80℃; for 5h;	75%
at 70℃;

p-toluenesulfonylanhydride (4124-41-8) + isopropyl alcohol (67-63-0) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
With ytterbium(III) triflate In dichloromethane at 20℃; for 24h;	87%

toluene-4-sulfonic acid (104-15-4) + diisopropyl phenylphosphonate (7237-16-3) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
In 1,2-dichloro-ethane at 40℃; for 48h;	82%

triisopropyl phosphate (513-02-0) + toluene-4-sulfonic acid (104-15-4) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
In 1,2-dichloro-ethane at 40℃; for 72h; Product distribution; investigate effect of molar ratio, solvent, temperature and reaction time;	77%
In 1,2-dichloro-ethane at 40℃; for 72h;	77%

isopropoxytrimethylsilane (1825-64-5) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
With FeCl3-Montmorillonite K-10 In acetonitrile for 9h; Heating;	77%

sodium 4-methylbenzenesulfinate (824-79-3) + isopropyl alcohol (67-63-0) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
With [bis(acetoxy)iodo]benzene at 20℃; for 0.25h;	74%

triisopropyl phosphite (116-17-6) + toluene-4-sulfonic acid (104-15-4) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
In 1,2-dichloro-ethane for 72h; Product distribution; Ambient temperature; investigate effect of reaction time;	71%
In 1,2-dichloro-ethane for 72h; Ambient temperature;	71%

2-isopropoxytetrahydropyran (1927-70-4) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
With FeCl3-Montmorillonite K-10 In acetonitrile for 10h; Heating;	70%

triisopropyl phosphite (116-17-6) + (3,3-dimethylbutynyl)(phenyl)iodonium tosylate (92473-47-7) → toluene-4-sulfonic acid isopropyl ester (2307-69-9) + Diisopropyl (tert-butylethynyl)phosphonate (125172-82-9)

Conditions	Yield
at 95℃; for 1.5h;	A n/a B 58%

diethyl 2-propyl phosphate (2736-99-4) + toluene-4-sulfonic acid (104-15-4) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
at 40℃;	49%

4-methylbenzenediazonium tetrafluoroborate (459-44-9) + isopropyl alcohol (67-63-0) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

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;	43%

di-isopropyl ether (108-20-3) + acetyl p-toluenesulfonate (26908-82-7) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

2-iodo-propane (75-30-9) + toluene-4-sulfonic acid (104-15-4) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

Conditions	Yield
With silver(l) oxide 1) acetonitrile; 2) acetonitrile, RT, 24 h; Yield given. Multistep reaction;

toluene (108-88-3) → toluene-4-sulfonic acid isopropyl ester (2307-69-9)

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

1-(phenylsulphenyl)piperidylamide (29959-86-2) + toluene-4-sulfonic acid (104-15-4) + isopropyl alcohol (67-63-0) → toluene-4-sulfonic acid isopropyl ester (2307-69-9) + 1-(S-phenylsulfonimidoyl)piperidine (1523523-71-8)

Conditions	Yield
With ammonium carbamate; iodosylbenzene at 25℃; for 1h; Inert atmosphere;

9,10-dihydrolysergic acid + toluene-4-sulfonic acid isopropyl ester (2307-69-9) → 1-(1-methylethyl)-6-methylergoline-8-carboxylic acid

Conditions	Yield
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dimethyl sulfoxide; ethyl acetate	98.8%
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dimethyl sulfoxide; ethyl acetate	98.8%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + Diphenylphosphine oxide (4559-70-0) → isopropyl-diphenyl-phosphine oxide (2959-75-3)

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran at 65℃; for 10h;	94%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) → triisopropylheptaphosphine (87982-60-3, 87219-71-4, 87248-69-9)

Conditions	Yield
With trisodium heptaphosphide In tetrahydrofuran at -70 - 20℃; for 4h;	94%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + (15β,16α)-16-hydroxy-15-(hydroxymethyl)beyeran-18-oic acid (882175-40-8) → i-propyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate (1143505-98-9)

Conditions	Yield
With potassium carbonate In acetonitrile	92%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + Arctigenin (26687-82-1, 81446-30-2, 84413-77-4, 87678-74-8, 87678-75-9, 144901-91-7, 7770-78-7) → C24H30O6 (1443128-07-1)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 3h;	88%

3-hydroxy-4-methylthiazole-2(3H)-thione (49762-08-5) + toluene-4-sulfonic acid isopropyl ester (2307-69-9) → N-isopropoxy-4-methylthiazole-2(3H)thione

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In acetonitrile at 20℃; for 24h;	85%

C5H6NOS2(1-)*C16H36N(1+) + toluene-4-sulfonic acid isopropyl ester (2307-69-9) → N-isopropoxy-4,5-dimethylthiazole-2(3H)-thione (1092776-00-5)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 12h;	82%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + 4-{[2-(cyclohexylcarbamoyl)ethyl]methylamino}-1,3,4,5-tetrahydrobenz(cd)indole (150403-78-4) → 4-<<2-(cyclohexylcarbamoyl)ethyl>methylamino>-1-isopropyl-1,3,4,5-tetrahydrobenzindole

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 2h;	78%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + potassium triisopropylsilane-thiolate → triisopropyl(isopropylthio)silane

Conditions	Yield
In tetrahydrofuran 1.) -78 deg C up to RT; 2.) RT, 4 h;	75%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) → sodium diisopropylheptaphosphide

Conditions	Yield
With trisodium heptaphosphide In tetrahydrofuran at -70 - 20℃; for 4h;	74%

styrene (292638-84-7) + toluene-4-sulfonic acid isopropyl ester (2307-69-9) → 2-phenyl-3-methylbutanol (90499-41-5)

Conditions	Yield
Stage #1: styrene; toluene-4-sulfonic acid isopropyl ester With 2-cyclohexylethylmagnesium bromide; zirconocene dichloride In tetrahydrofuran at 55℃; for 12h; Stage #2: With oxygen In tetrahydrofuran at 0℃; Further stages.;	73%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + N-(hydroxy)-5-(p-methoxyphenyl)-4-(methyl)thiazole-2(3H)-thione tetraethylammonium salt → N-(isopropoxy)-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione (902757-39-5)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	73%

3-hydroxy-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione tetrabutylammonium salt + toluene-4-sulfonic acid isopropyl ester (2307-69-9) → N-(isopropoxy)-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione (902757-39-5)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 12h;	73%
In N,N-dimethyl-formamide at 20℃; Darkness;

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + (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 → (S)-10-(4-(1-isopropyl-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;	72.6%

glyoxalic acid ethylthioacetal (10490-06-9) + toluene-4-sulfonic acid isopropyl ester (2307-69-9) → 2,2-bis(ethylthio)-3-methylbutanoic acid (71535-45-0)

Conditions	Yield
With oxonium; potassium hexamethylsilazane In tetrahydrofuran at 25℃; for 2.5h; Product distribution; reactant;	72%
(i) HN(SiMe3)2, KH, THF, (ii) /BRN= 1876576/, (iii) aq. HCl; Multistep reaction;
With hydrogenchloride; potassium hydride; 1,1,1,3,3,3-hexamethyl-disilazane 1.) THF, 0 deg C, 15 min; THF, 25 deg C, 2.5 h.; Yield given. Multistep reaction;

2H-chromene (254-04-6) + toluene-4-sulfonic acid isopropyl ester (2307-69-9) → 2-(1-(1-methylethyl)prop-2-enyl)-phenol

Conditions	Yield
With zirconocene dichloride; butyl magnesium bromide In tetrahydrofuran at 55℃; for 12h; Alkylation;	71%

C10H7ClNOS2(1-)*C16H36N(1+) + toluene-4-sulfonic acid isopropyl ester (2307-69-9) → N-isopropoxy-5-(4-chlorophenyl)-4-methylthiazole-2(3H)-thione (1092776-06-1)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 12h;	71%

tributyl methyl ammonium salt of trimethyl methylenebisphosphonate + toluene-4-sulfonic acid isopropyl ester (2307-69-9) → dimethyl {[isopropoxy(methoxy)phosphoryl]methyl}phosphonate (133918-73-7)

Conditions	Yield
In acetonitrile Reflux;	71%

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + N-hydroxy-4-(p-methylphenyl)thiazole-2(3H)-thione (220222-19-5) → 3-Isopropoxy-4-p-tolyl-3H-thiazole-2-thione (220222-34-4)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In acetonitrile at 20℃; for 36h;	70%

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 7237-16-3 diisopropyl phenylphosphonate 
• 4124-41-8 p-toluenesulfonylanhydride 
• 67-63-0 isopropyl alcohol 
• 29959-86-2 1-(phenylsulphenyl)piperidylamide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 108-88-3 toluene 
• 1825-64-5 isopropoxytrimethylsilane 
• 98-59-9 p-toluenesulfonyl chloride 
• 1927-70-4 2-isopropoxytetrahydropyran 
• 143885-03-4 isopropyloxy(diphenyl)-λ⁶-sulfanenitrile 
• 513-02-0 triisopropyl phosphate 
• 2736-99-4 diethyl 2-propyl phosphate 

Downstream Products

• 2944-47-0 o-isopropylanisole 
• 4132-48-3 1-methoxy-4-(1-methylethyl)benzene 
• 104-15-4 toluene-4-sulfonic acid 
• 67-63-0 isopropyl alcohol 
• 19646-38-9 toluene-4-sulfinyloxyl 
• 187737-37-7 propene 
• 536-57-2 p-toluene sulfinic acid 
• 80304-54-7 (1-bromo-2-methylpropyl)benzene 
• 35071-66-0 1-isopropylcyclopentadiene 
• 75-26-3 isopropyl bromide 
• 7515-80-2 N-isopropyl-N-tert-butylamine 
• 1540-21-2 Ethyl-β-isopropyloxycrotonat 
• 2253-73-8 isopropyl isothiocyanate 
• 6158-45-8 1-isopropylnaphthalene 

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Method for the Preparation of Diamine Derivative

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