78521-39-8

Basic information

• Product Name: 6-[[(4-methylphenyl)sulphonyl]amino]hexanoic acid
• Synonyms: 6-[[(4-methylphenyl)sulphonyl]amino]hexanoic acid;4-Methylphenylsulfonylaminohexanoicacid;6-[[(4-methylphenyl) sulfonyl] amino] -Hexanoic acid;4-METHYLPHENYLSULFONYLAMINOHEXANOIC ACID OR N-(HEXANOIC ACID ) P-TOLUENESULFONAMIDE;Einecs 278-934-5;Hexanoic acid, 6-(((4-methylphenyl)sulfonyl)amino)-;Arylsulphonylamino carboxylic acid;6-(Toluene-4-sulfonylamino)-hexanoic acid
• CAS NO: 78521-39-8
• Molecular Formula: C₁₃H₁₉NO₄S
• Molecular Weight: 285.35926
• EINECS: 278-934-5
• Mol File: 78521-39-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 475.2 °C at 760 mmHg
• Flash Point: 241.2 °C
• Appearance: /
• Density: 1.222 g/cm³
• Vapor Pressure: 7.73E-10mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: 2-8°C
• PKA: 4.44[at 20 ℃]
• Water Solubility: 317mg/L at 25℃
• CAS DataBase Reference: 6-[[(4-methylphenyl)sulphonyl]amino]hexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[[(4-methylphenyl)sulphonyl]amino]hexanoic acid(78521-39-8)
• EPA Substance Registry System: 6-[[(4-methylphenyl)sulphonyl]amino]hexanoic acid(78521-39-8)

Safety Data

• Hazardous Substances Data: 78521-39-8(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C13H19NO4S/c1-11-6-8-12(9-7-11)19(17,18)14-10-4-2-3-5-13(15)16/h6-9,14H,2-5,10H2,1H3,(H,15,16)

Synthetic route

p-toluenesulfonyl chloride (98-59-9) + 6-aminohexanoic acid (60-32-2) → Tosyl-ε-aminocapronsaeure (78521-39-8)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran for 2h;	95%
With sodium carbonate In water at 90℃; for 1h;	80%
With sodium hydroxide

caprolactam (105-60-2) → Tosyl-ε-aminocapronsaeure (78521-39-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C / Inert atmosphere 2.1: lithium hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Inert atmosphere View Scheme

toluene-4-sulfonamide (70-55-3) → Tosyl-ε-aminocapronsaeure (78521-39-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C / Inert atmosphere 2.1: lithium hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Inert atmosphere View Scheme

1-(4-Methylbenzene)sulfonyl-2H-hexahydroazepin-2-one (23438-55-3) → Tosyl-ε-aminocapronsaeure (78521-39-8)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water at 20℃; for 0.5h; Inert atmosphere;

methanol (67-56-1) + Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-<<(4-Methylphenyl)sulfonyl>amino>hexansaeure-methylester (67370-67-6)

Conditions	Yield
With sulfuric acid at 25℃; for 48h;	100%

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-(4-methylphenylsulfonamido)hexanamide (100800-85-9)

Conditions	Yield
With urea at 180 - 200℃; for 4h;	60%

Tosyl-ε-aminocapronsaeure (78521-39-8) → 1-(4-Methylbenzene)sulfonyl-2H-hexahydroazepin-2-one (23438-55-3)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	42%
at 125℃; under 0.01 Torr;
With thionyl chloride
With phosphorus pentachloride

Tosyl-ε-aminocapronsaeure (78521-39-8) + dimethyl sulfate (77-78-1) → 6-[methyl-(toluene-4-sulfonyl)-amino]-hexanoic acid (6954-30-9)

Conditions	Yield
With sodium hydroxide

Tosyl-ε-aminocapronsaeure (78521-39-8) → N-Tosyl-ε-aminocapronsaeurechlorid (72676-81-4)

Conditions	Yield
With thionyl chloride
With thionyl chloride for 1h; Heating;

Tosyl-ε-aminocapronsaeure (78521-39-8) → C26H36N2O7S2

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.333333h; Condensation;
With dicyclohexyl-carbodiimide In 1,4-dioxane at 0℃;

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-(toluene-4-sulfonylamino)-hexanoic acid 3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-4-oxo-2-trifluoromethyl-4H-chromen-7-yl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: dicyclohexylcarbodiimide / tetrahydrofuran / 0.33 h / 0 °C 2: 4-dimethylaminopyridine / tetrahydrofuran / 0 °C View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → N-(5-Amino-pentyl)-4-methyl-benzenesulfonamide; hydrochloride (20255-86-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / urea / 4 h / 180 - 200 °C 2: 70 percent / 1.) phenyliodosyl bis(trifluoroacetate), 2.) HCl conc. / 1.) MeCN-H2O, RT, 6 h, 2.) H2O View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 3-(3-Cyano-phenyl)-2-[6-(toluene-4-sulfonylamino)-hexanoylamino]-propionic acid (93235-95-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 3-(4-Cyano-phenyl)-2-[6-(toluene-4-sulfonylamino)-hexanoylamino]-propionic acid (93235-96-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-(Toluene-4-sulfonylamino)-hexanoic acid [1-(3-cyano-benzyl)-2-oxo-2-piperidin-1-yl-ethyl]-amide (93235-99-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h 4: pyridine / 24 h / Ambient temperature View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-(Toluene-4-sulfonylamino)-hexanoic acid [1-(4-cyano-benzyl)-2-oxo-2-piperidin-1-yl-ethyl]-amide (93236-00-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h 4: pyridine / 24 h / Ambient temperature View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-(Toluene-4-sulfonylamino)-hexanoic acid [2-oxo-2-piperidin-1-yl-1-(3-thiocarbamoyl-benzyl)-ethyl]-amide (93236-01-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h 4: pyridine / 24 h / Ambient temperature 5: TEA, H2S / pyridine / 48 h / Ambient temperature View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-(Toluene-4-sulfonylamino)-hexanoic acid [2-oxo-2-piperidin-1-yl-1-(4-thiocarbamoyl-benzyl)-ethyl]-amide (93236-02-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h 4: pyridine / 24 h / Ambient temperature 5: TEA, H2S / pyridine / 48 h / Ambient temperature View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 3-(4-Cyano-phenyl)-2-[6-(toluene-4-sulfonylamino)-hexanoylamino]-propionic acid 4-nitro-phenyl ester (93235-98-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 3-(3-Cyano-phenyl)-2-[6-(toluene-4-sulfonylamino)-hexanoylamino]-propionic acid 4-nitro-phenyl ester (93235-97-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → Nα-Tosyl-(ε-aminocapronyl)-3-amidinophenylalaninpiperididhydroiodid (93236-05-6)

Conditions	Yield
Multi-step reaction with 7 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h 4: pyridine / 24 h / Ambient temperature 5: TEA, H2S / pyridine / 48 h / Ambient temperature 6: 0.3 g / acetone / 48 h / Ambient temperature 7: 45 percent / CH3COONH4 / ethanol / 2.5 h / 60 °C View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → Nα-Tosyl-(ε-aminocapronyl)-4-amidinophenylalaninpiperididhydroiodid (93236-06-7)

Conditions	Yield
Multi-step reaction with 7 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h 4: pyridine / 24 h / Ambient temperature 5: TEA, H2S / pyridine / 48 h / Ambient temperature 6: 0.3 g / acetone / 48 h / Ambient temperature 7: 60 percent / CH3COONH4 / ethanol / 2.5 h / 60 °C View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 3-{3-Oxo-3-piperidin-1-yl-2-[6-(toluene-4-sulfonylamino)-hexanoylamino]-propyl}-thiobenzimidic acid methyl ester; hydriodide (93236-03-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h 4: pyridine / 24 h / Ambient temperature 5: TEA, H2S / pyridine / 48 h / Ambient temperature 6: 0.3 g / acetone / 48 h / Ambient temperature View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 4-{3-Oxo-3-piperidin-1-yl-2-[6-(toluene-4-sulfonylamino)-hexanoylamino]-propyl}-thiobenzimidic acid methyl ester; hydriodide (93236-04-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: SOCl2 / 1 h / Heating 2: NaOH (1 mol/l) / benzene; H2O / 12 h 3: DCC / pyridine / 24 h 4: pyridine / 24 h / Ambient temperature 5: TEA, H2S / pyridine / 48 h / Ambient temperature 6: 0.3 g / acetone / 48 h / Ambient temperature View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6,6'-<<(4-Methylphenyl)sulfonyl>imino>bishexansaeure (63702-61-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / conc. H2SO4 / 48 h / 25 °C 2: potassium t-butylate / 2-methyl-propan-2-ol / 24 h / Heating 3: NaOH / H2O; ethanol / Heating View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6,6'-<<(4-Methylphenyl)sulfonyl>imino>bis(hexanoylchlorid) (63730-77-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / conc. H2SO4 / 48 h / 25 °C 2: potassium t-butylate / 2-methyl-propan-2-ol / 24 h / Heating 3: NaOH / H2O; ethanol / Heating 4: 95 percent / oxalyl chloride / benzene / 48 h / Ambient temperature View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 1-<(4-Methylphenyl)sulfonyl>-1,8,15-triazacycloheneicosan (63702-63-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: 100 percent / conc. H2SO4 / 48 h / 25 °C 2: potassium t-butylate / 2-methyl-propan-2-ol / 24 h / Heating 3: NaOH / H2O; ethanol / Heating 4: 95 percent / oxalyl chloride / benzene / 48 h / Ambient temperature 5: 55 percent / toluene / 0 - 2 °C 6: 1.) 1N BH3, 2.) 6N HCl / 1.) THF, 1 h, room temp., 2 h, reflux, 2.) ethanol, 1 h, reflux View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-[(5-Methoxycarbonyl-pentyl)-(toluene-4-sulfonyl)-amino]-hexanoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / conc. H2SO4 / 48 h / 25 °C 2: potassium t-butylate / 2-methyl-propan-2-ol / 24 h / Heating View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 8-<(4-Methylphenyl)sulfonyl>-1,8,15-triazacycloheneicosan-2,14-dion (63702-62-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 100 percent / conc. H2SO4 / 48 h / 25 °C 2: potassium t-butylate / 2-methyl-propan-2-ol / 24 h / Heating 3: NaOH / H2O; ethanol / Heating 4: 95 percent / oxalyl chloride / benzene / 48 h / Ambient temperature 5: 55 percent / toluene / 0 - 2 °C View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 8,22-Bis<(4-methylphenyl)sulfonyl>-1,8,15,22-tetraazabicyclo<13.13.6>tetratriacontan (63702-65-8)

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / conc. H2SO4 / 48 h / 25 °C 2: potassium t-butylate / 2-methyl-propan-2-ol / 24 h / Heating 3: NaOH / H2O; ethanol / Heating 4: 95 percent / oxalyl chloride / benzene / 48 h / Ambient temperature 5: 55 percent / toluene / 0 - 2 °C 6: 1.) 1N BH3, 2.) 6N HCl / 1.) THF, 1 h, room temp., 2 h, reflux, 2.) ethanol, 1 h, reflux 7: 50 percent / triethylamine / benzene; toluene 8: 1.) 1M BH3, 2.) conc. H2SO4 / 1.) THF, 1 h, ice-bath temp. to room temp., 14 h, reflux, 2.) ethanol, reflux View Scheme
Multi-step reaction with 6 steps 1: 100 percent / conc. H2SO4 / 48 h / 25 °C 2: potassium t-butylate / 2-methyl-propan-2-ol / 24 h / Heating 3: NaOH / H2O; ethanol / Heating 4: 95 percent / oxalyl chloride / benzene / 48 h / Ambient temperature 5: 50 percent / triethylamine / benzene; toluene 6: 1.) 1M BH3, 2.) conc. H2SO4 / 1.) THF, 1 h, ice-bath temp. to room temp., 14 h, reflux, 2.) ethanol, reflux View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 8,22-Bis<(4-methylphenyl)sulfonyl>-1,8,15,22-tetraazabicyclo<13.13.6>tetratriacontan-2,14-dion (63702-64-7)

Conditions	Yield
Multi-step reaction with 7 steps 1: 100 percent / conc. H2SO4 / 48 h / 25 °C 2: potassium t-butylate / 2-methyl-propan-2-ol / 24 h / Heating 3: NaOH / H2O; ethanol / Heating 4: 95 percent / oxalyl chloride / benzene / 48 h / Ambient temperature 5: 55 percent / toluene / 0 - 2 °C 6: 1.) 1N BH3, 2.) 6N HCl / 1.) THF, 1 h, room temp., 2 h, reflux, 2.) ethanol, 1 h, reflux 7: 50 percent / triethylamine / benzene; toluene View Scheme
Multi-step reaction with 5 steps 1: 100 percent / conc. H2SO4 / 48 h / 25 °C 2: potassium t-butylate / 2-methyl-propan-2-ol / 24 h / Heating 3: NaOH / H2O; ethanol / Heating 4: 95 percent / oxalyl chloride / benzene / 48 h / Ambient temperature 5: 50 percent / triethylamine / benzene; toluene View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-(methylamino)hexanoic acid (26410-96-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH-solution 2: hydrochloric acid / 100 °C View Scheme

Tosyl-ε-aminocapronsaeure (78521-39-8) → 6-(N-methyl-ureido)-hexanoic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOH-solution 2: hydrochloric acid / 100 °C 3: hydrochloric acid View Scheme

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 60-32-2 6-aminohexanoic acid 
• 23438-55-3 1-(4-Methylbenzene)sulfonyl-2H-hexahydroazepin-2-one 
• 70-55-3 toluene-4-sulfonamide 
• 105-60-2 caprolactam 

Downstream Products

• 23438-55-3 1-(4-Methylbenzene)sulfonyl-2H-hexahydroazepin-2-one 
• 4323-49-3 N--ε-aminocapronsaeure 
• 4348-09-8 6-({2'-[6-(Toluene-4-sulfonylamino)-hexanoylamino]-biphenyl-4-carbonyl}-amino)-hexanoic acid 
• 27370-45-2 2'-[6-(Toluene-4-sulfonylamino)-hexanoylamino]-biphenyl-4-carboxylic acid 
• 26410-96-8 6-(methylamino)hexanoic acid 
• 63702-64-7 8,22-Bis<(4-methylphenyl)sulfonyl>-1,8,15,22-tetraazabicyclo<13.13.6>tetratriacontan-2,14-dion 
• 63702-65-8 8,22-Bis<(4-methylphenyl)sulfonyl>-1,8,15,22-tetraazabicyclo<13.13.6>tetratriacontan 
• 63702-62-5 8-<(4-Methylphenyl)sulfonyl>-1,8,15-triazacycloheneicosan-2,14-dion 
• 63702-63-6 1-<(4-Methylphenyl)sulfonyl>-1,8,15-triazacycloheneicosan 
• 63730-77-8 6,6'-<<(4-Methylphenyl)sulfonyl>imino>bis(hexanoylchlorid) 
• 63702-61-4 6,6'-<<(4-Methylphenyl)sulfonyl>imino>bishexansaeure 
• 93236-04-5 4-{3-Oxo-3-piperidin-1-yl-2-[6-(toluene-4-sulfonylamino)-hexanoylamino]-propyl}-thiobenzimidic acid methyl ester; hydriodide 
• 93236-03-4 3-{3-Oxo-3-piperidin-1-yl-2-[6-(toluene-4-sulfonylamino)-hexanoylamino]-propyl}-thiobenzimidic acid methyl ester; hydriodide 
• 93236-06-7 N_α-Tosyl-(ε-aminocapronyl)-4-amidinophenylalaninpiperididhydroiodid 

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