636-73-7

Basic information

• Product Name: 3-Pyridinesulfonic acid
• Synonyms: 3-sulfopyridine;beta-sulfopyridine;3-PYRIDINESULPHONIC ACID;3-PYRIDINESULFONIC ACID;3-PyridinesulphonicAcid98%;Pyridine-3-sulfonicacid,98+%;3-Pyridinesulfonic;3-PYRIDYLSULPHONICACID
• CAS NO: 636-73-7
• Molecular Formula: C₅H₅NO₃S
• Molecular Weight: 159.16
• EINECS: 211-265-9
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Pyridine;Organic acids;Heterocycle-Pyridine series
• Mol File: 636-73-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: >300 °C(lit.)
• Flash Point: > 66
• Appearance: White to almost white/Crystalline Powder
• Density: 1.7130
• Refractive Index: 1.5480 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: -2.30±0.18(Predicted)
• Water Solubility: soluble
• Sensitive: Light Sensitive
• BRN: 120822
• CAS DataBase Reference: 3-Pyridinesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinesulfonic acid(636-73-7)
• EPA Substance Registry System: 3-Pyridinesulfonic acid(636-73-7)

Safety Data

• Hazard Codes: C
• Statements: 34-22
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 2585 8/PG 3
• WGK Germany: 3
• RTECS: UT7920000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 636-73-7(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white crystalline powder

Uses

3-Pyridinesulfonic acid can be used in the synthesis of reaction intermediates, such as silver 3-pyridinesulfonate and 3-pyridinesulfonyl chloride.

Purification Methods

Purify the acid by recrystallisation from H2O or aqueous EtOH as needles or plates. [pKa: Evans & Brown J Org Chem 27 3127 1962, IR: Arnett & Chawla J Am Chem Soc 100 214 1978.] UV in 50% aqueous EtOH has at 208 and 262nm. The ammonium salt max has m 243o (from H2O), the sulfonyl chloride has m 133-134o (from pet ether), the amide has m 110-111o (from H2O), the hydrochloride has m >300o(dec), and the N-methyl betaine has m 130o (from H2O). [Gastel & Wibaut Recl Trav Chim Pays-Bas 53 1031 1934, McIlvain & Goese J Am Chem Soc 65 2233 1943, Machek Monatsh Chem 72 77 1938, Beilstein 22 I 616, 22 II 309, 22/7 V 552.]

InChI:InChI=1/C5H5NO3S/c7-10(8,9)5-2-1-3-6-4-5/h1-4H,(H,7,8,9)/p-1

Synthetic route

pyridine (110-86-1) → 3-pyridinesulfonic acid (636-73-7)

Conditions	Yield
With sulfuric acid at 320 - 330℃; im Rohr;
With vanadium sulfate; sulfuric acid
With sulfur trioxide; mercury(II) sulfate at 225 - 235℃;

4-amino-pyridine-3-sulfonic acid (29452-57-1) → 3-pyridinesulfonic acid (636-73-7)

Conditions	Yield
Diazotization;

pyridine (110-86-1) + sulfuric acid (7664-93-9) → 3-pyridinesulfonic acid (636-73-7)

pyridine (110-86-1) + sulfuric acid (7664-93-9) + sulfur trioxide (7446-11-9) → 3-pyridinesulfonic acid (636-73-7)

pyridine (110-86-1) + sulfuric acid (7664-93-9) + mercury(II) sulfate → 3-pyridinesulfonic acid (636-73-7)

Conditions	Yield
at 260℃;

diazotized 4-amino-pyridine-sulfonic acid-(3) → 3-pyridinesulfonic acid (636-73-7)

Conditions	Yield
With ethanol nachfolgend Eindampfen auf dem Wasserbad;

pyridine (110-86-1) + sulfuric acid-monohydrate → 3-pyridinesulfonic acid (636-73-7)

pyridine (110-86-1) + sulfuric acid (7664-93-9) + mercury(II) sulfate → pyridin-4-ol (626-64-2) + pyridine-4-sulfonic acid (5402-20-0) + 3-pyridinesulfonic acid (636-73-7)

Conditions	Yield
at 330℃;

piperidine (110-89-4) + sulfuric acid (7664-93-9) → pyridine (110-86-1) + 3-pyridinesulfonic acid (636-73-7) + pyridine-disulfonic acid-(3.5)

Conditions	Yield
at 300℃;

3-HYDROXYPYRIDINE (109-00-2) → 3-pyridinesulfonic acid (636-73-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc-dust / durch Destillation 2: concentrated sulfuric acid View Scheme

3-chloropyridine-N-oxide (1851-22-5) → 3-pyridinesulfonic acid (636-73-7)

Conditions	Yield
With sodium hydroxide; sodium hydrogensulfite; aluminum nickel In water
With hydrogenchloride; sodium hydroxide; dihydrogen peroxide; sodium sulfite; aluminum nickel In ethanol; water; ethylene glycol; isopropyl alcohol

3-pyridinesulfonic acid (636-73-7) → Pyridine-3-sulfonyl chloride (16133-25-8)

Conditions	Yield
With phosphorus pentachloride In trichlorophosphate at 120℃; for 12h;	98%
With phosphorus pentachloride; trichlorophosphate for 3h; Heating / reflux;	94%
With phosphorus pentachloride In toluene Heating;	92%

3-pyridinesulfonic acid (636-73-7) → pyridine-3-sulfonyl chloride hydrochloride (42899-76-3)

Conditions	Yield
Stage #1: 3-pyridinesulfonic acid With phosphorus pentachloride; trichlorophosphate at 120℃; Stage #2: With hydrogenchloride In dichloromethane at 5℃; Further stages.;	97%
Stage #1: 3-pyridinesulfonic acid With phosphorus pentachloride; trichlorophosphate at 120℃; for 15h; Stage #2: With hydrogenchloride In chloroform	83%
Stage #1: 3-pyridinesulfonic acid With phosphorus pentachloride; trichlorophosphate at 120℃; for 8h; Stage #2: With hydrogenchloride In chloroform at 20℃;	81%

3-pyridinesulfonic acid (636-73-7) → pyridine-2-sulfonyl azide (2432-67-9)

Conditions	Yield
Stage #1: 3-pyridinesulfonic acid With trichloroisocyanuric acid; triphenylphosphine In tetrahydrofuran at 0 - 5℃; Stage #2: With sodium azide In tetrahydrofuran at 5 - 20℃;	94%
Multi-step reaction with 2 steps 1.1: PCl5; POCl3 / 120 °C 1.2: 97 percent / HCl / CH2Cl2 / 5 °C 2.1: 80 percent / NaN3 / H2O; acetone / 20 °C View Scheme
Multi-step reaction with 2 steps 1: PCl5 2: 80 percent / NaN3 / H2O / 1 h View Scheme

3-pyridinesulfonic acid (636-73-7) → N-fluoropyridinium-3-sulfonate

Conditions	Yield
With Amberlite IRA-94S; fluorine In various solvent(s) bath temperature 0 deg C;	87%

3-pyridinesulfonic acid (636-73-7) + N-(4-aminophenyl)pyridine-3-sulfonamide → N,N'-(1,4-phenylene)bis(pyridine-3-sulfonamide)

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 5h;	72%

3-pyridinesulfonic acid (636-73-7) + bis(4-pyridyl) disulfide (2645-22-9) + water (7732-18-5) + zinc(II) carbonate (743369-26-8) → Zn(4,4'-dipyridyldisulfide)2(H2O)2(pyridine-3-sulfonate)2

Conditions	Yield
In ethanol; water suspn. of ZnCO3 in hot H2O slowly added to soln. of 2 equiv. of pyridine-3-sulfonic acid in H2O, treated with 2 equiv. of 4,4'-dipyridyldisulfide in EtOH, stirred at room temp. for 1 week; crystd. at room temp. for 15 d;	70%

3-pyridinesulfonic acid (636-73-7) + bis(4-pyridyl) disulfide (2645-22-9) + Cu(II)(fumarate)2(H2O)2 + water (7732-18-5) → Cu(4,4'-dipyridyldisulfide)2(H2O)2(fumatate)2*4H2O

Conditions	Yield
In ethanol; water suspn. of Cu complex in H2O slowly treated with 2 equiv. of pyridine-3-sulfonic acid in C2H5OH, refluxed for 1 h; cooled to room temp., washed (H2O), dried (vac.), elem. anal.;	69%

3-pyridinesulfonic acid (636-73-7) + diethyl ether (60-29-7) + dichloromethane (75-09-2) → 3-pyridinesulfonamide (2922-45-4)

Conditions	Yield
With pyridine; dmap In water	68.9%

3-pyridinesulfonic acid (636-73-7) + [ruthenium(2,2′-bipyridine-6,6′-dicarboxylate)(dimethyl sulfoxide)2] → [RuII(2,2'-bipyridine-6,6'-dicarboxylate)(PySO3Na)2]

Conditions	Yield
With sodium carbonate In methanol Inert atmosphere; Reflux;	62.3%

3-pyridinesulfonic acid (636-73-7) + [Pt(N,N-dimethylbenzylamine-κN,κC)(μ-Cl)]2 → {(2-dimethylaminomethylphenyl-C,N)(3-pyridinesulfono-N)(aqua)platinum(II)}

Conditions	Yield
In water byproducts: HCl; to a suspn. of the complex in water was added the sulfonic acid, stirred for 2 d at 50°C; filtered, washed with cold water, dried in air, washed with CH2Cl2, dried in air; elem. anal.;	62%

3-pyridinesulfonic acid (636-73-7) + cobalt(II) diacetate tetrahydrate (6147-53-1) → bis(pyridine-3-sulfonate)tetraaquacobalt(II) (38314-68-0)

Conditions	Yield
With NaOH In water mixt. of Co salt and ligand (1:2) heated at 80°C under stirring, pH adjusted to 5.0 (NaOH); crystd. at room temp. in air for 2 weeks, elem. anal.;	62%

3-pyridinesulfonic acid (636-73-7) + N‑(4‑aminophenyl)‑3,4,5‑trimethoxybenzamide → 3,4,5-trimethoxy-N-(4-(pyridine-3-sulfonamido)phenyl)benzamide

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 5h;	60%

3-pyridinesulfonic acid (636-73-7) + C12H6N2O4(2-)*Ru(2+)*C9H15N2(1+)*C2H6OS*C2H3N*Br(1-) → C26H25N5O7RuS

Conditions	Yield
With triethylamine In methanol for 3h; Inert atmosphere; Reflux;	60%

3-pyridinesulfonic acid (636-73-7) + hexamethylenetetramine (100-97-0) + water (7732-18-5) + silver(I) acetate (563-63-3) → 2Ag(1+)*(CH2)2N(CH2)N(CH2)N(CH2)N(CH2)*2(C5H4N)SO3(1-)*2H2O=[Ag2(H2O)((C5H4N)SO3)2(C6H12N4)]*H2O

Conditions	Yield
With NH3 In water pyridine-3-sulfonic acid and hexamethylenetetramine (1:1 mol) added to aq. soln. of MeCOOAg (1 mol); mixt. stirred for 15 min; ppt. dissolved byaddn. of 14 M aq. soln. NH3; evapd. at room temp. for 5 d; elem. anal.;	52%

3-pyridinesulfonic acid (636-73-7) + Iodoacetic acid (64-69-7) → N-carboxymethyl-3-pyridine sulfonic acid

Conditions	Yield
With silver(l) oxide 1) H2O, 3.5 h, 2) 2-propanol, RT, 3 d;	50%

3-pyridinesulfonic acid (636-73-7) + copper(II) nitrate trihydrate → bis(pyridine-3-sulfonate)diaquacopper(II)

Conditions	Yield
With NaOH In water mixt. of Cu salt and ligand (1:2) heated at 80°C under stirring, pH adjusted to 5.0 (NaOH); crystd. at room temp. in air for 2 weeks, elem. anal.;	48%

3-pyridinesulfonic acid (636-73-7) + 1,4-phenylenediamine (106-50-3) → N-(4-aminophenyl)pyridine-3-sulfonamide

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 5h;	45%

methanol (67-56-1) + 3-pyridinesulfonic acid (636-73-7) + 2,2'-bipyridine-6,6'-dicarboxylic acid (4479-74-7) + cis-[Ru(dmso)4Cl2] + triethylamine (121-44-8) → [HNEt3]2[RuII(2,2′-bipyridine-6,6′-dicarboxylate)(3-SO3-pyridine)2]*2methanol

Conditions	Yield
Stage #1: 2,2'-bipyridine-6,6'-dicarboxylic acid; cis-[Ru(dmso)4Cl2]; triethylamine In methanol for 3h; Reflux; Inert atmosphere; Stage #2: methanol; 3-pyridinesulfonic acid Inert atmosphere; Reflux;	31%

3-pyridinesulfonic acid (636-73-7) + mercury(I) nitrate → Bis[pyridin(3)-sulfonat]diquecksilber(I)-dihydrat

Conditions	Yield
In water pyridine sulfonic acid added to HgNO3, kept for 3-4 h; filtered, washed with H2O, dried in vac., elem. anal.;	30%

3-pyridinesulfonic acid (636-73-7) + dichlorotetrakis(dimethylsulfoxide)ruthenium(II) + 3,5-bis{6-(2,2’-bipyridyl)}-4-methyl-1H-pyrazole + water (7732-18-5) + sodium hydroxide (1310-73-2) → C44H35N10O14Ru2S4(3-)*3Na(1+)*7.5H2O

Conditions	Yield
Stage #1: dichlorotetrakis(dimethylsulfoxide)ruthenium(II); 3,5-bis{6-(2,2’-bipyridyl)}-4-methyl-1H-pyrazole With triethylamine In ethanol for 2h; Inert atmosphere; Schlenk technique; Reflux; Stage #2: 3-pyridinesulfonic acid; water; sodium hydroxide Inert atmosphere; Schlenk technique; Reflux;	22%

3-pyridinesulfonic acid (636-73-7) + bis(4-pyridyl) disulfide (2645-22-9) + copper(II) acetate monohydrate (6046-93-1) → Cu(4,4'-dipyridyldisulfide)2(H2O)2(pyridine-3-sulfonate)2

Conditions	Yield
In ethanol; water soln. of 2 equiv. of pyridine-3-sulfonic acid in H2O added slowly to soln. of Cu salt in H2O, layered with EtOH soln. of 4,4'-dipyridyldisulfide(1 equiv.); crystd. at room temp.;	21%

3-pyridinesulfonic acid (636-73-7) → 3-HYDROXYPYRIDINE (109-00-2)

Conditions	Yield
Alkalischmelze;
bei der Kalischmelze;
With sodium hydroxide at 160 - 210℃; for 3h; Temperature;

3-pyridinesulfonic acid (636-73-7) → 3,3'-bipyridine (581-46-4)

Conditions	Yield
bei der trocknen Destillation;

3-pyridinesulfonic acid (636-73-7) → 4-amino-3,5-dibromopyridine (84539-34-4)

Conditions	Yield
With bromine

3-pyridinesulfonic acid (636-73-7) + 7β-<2-(2-aminothiazol-4yl)-2-(Z)-methoximinoacetamide>-3-iodomethyl-2-<(trimethylsilyloxy)carbonyl>cephalosporin (83421-24-3) → C19H18N6O8S3 (127400-03-7)

Conditions	Yield
With methanol 1.) acetonitrile, RT, 3 h, 2.) acetone; Multistep reaction;

3-pyridinesulfonic acid (636-73-7) → pyridine-3-thiol (16133-26-9)

Conditions	Yield
Yield given. Multistep reaction;

3-pyridinesulfonic acid (636-73-7) + descarboethoxyloratadine (100643-71-8) → 8-chloro-11-(1-(pyridin-3-ylsulfonyl)piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Conditions	Yield
With dmap; 4-Nitrobenzenesulfonyl chloride 1.) pyridine, 0 deg C, 7 h, 2.) 0 deg C, 1 h; 20 deg C, overnight; Yield given. Multistep reaction;

3-pyridinesulfonic acid (636-73-7) + 8-Chloro-11-piperidin-(3E)-ylidene-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (183554-81-6) → 8-Chloro-11-[1-(pyridine-3-sulfonyl)-piperidin-(3E)-ylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine + 8-Chloro-11-[1-(4-nitro-benzenesulfonyl)-piperidin-(3E)-ylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Conditions	Yield
With dmap; 4-Nitrobenzenesulfonyl chloride 1.) pyridine, 0 deg C, 7 h, 2.) 0 deg C, 1 h; 20 deg C, overnight; Yield given. Multistep reaction. Yields of byproduct given;

Upstream product

• 110-86-1 pyridine 
• 29452-57-1 4-amino-pyridine-3-sulfonic acid 
• 110-89-4 piperidine 
• 7664-93-9 sulfuric acid 
• 1851-22-5 3-chloropyridine-N-oxide 
• 7446-11-9 sulfur trioxide 
• 109-00-2 3-HYDROXYPYRIDINE 

Downstream Products

• 109-00-2 3-HYDROXYPYRIDINE 
• 581-46-4 3,3'-bipyridine 
• 16133-25-8 Pyridine-3-sulfonyl chloride 
• 16133-26-9 pyridine-3-thiol 
• 42899-76-3 pyridine-3-sulfonyl chloride hydrochloride 
• 110-86-1 pyridine 
• 65227-53-4 pyridine-3-sulfonohydrazide 
• 343234-93-5 C₁₅H₁₅N₃O₃S 

Relevant articles and documents

Production of pyridine-3-sulfonic acid

A method for the production of heavy metal-free pyridine -3-sulfonic acid by oxidation of 3-chloro-pyridine to 3-chloro-pyridine-N-oxide, substitution of the chlorine through a sulfonic acid group, and subsequent reduction to pyridine-3-sulfonic acid. The method can be carried out using raw 3-chloropyridine-N-oxide and direct further reaction of the pyridine-3-sulfonic acid-N-oxide in the presence of Raney nickel in an alkaline solution.