16133-25-8

Basic information

• Product Name: PYRIDINE-3-SULFONYL CHLORIDE HYDROCHLORIDE
• Synonyms: 3-CHLOROSULFONYL-PYRIDINIUM, CHLORIDE;3-PYRIDINESULFONYL CHLORIDE, HCL;3-PYRIDINESULFONYL CHLORIDE HYDROCHLORIDE;PYRIDINE-3-SULFONYL CHLORIDE HYDROCHLORIDE;PYRIDINE-3-SULPHONYL CHLORIDE HYDROCHLORIDE;3-Pyridine sulphonyl chloride;pyridine-3-sulfonyl chloride(SALTDATA: 0.8HCl 0.3H2O);m-Pyridinesulfonyl chloride
• CAS NO: 16133-25-8
• Molecular Formula: C5H4ClNO2S
• Molecular Weight: 177.61
• EINECS: -0
• Mol File: 16133-25-8.mol
• Article Data: 45

Chemical Properties

• Melting Point: 144 °C
• Boiling Point: 284℃
• Flash Point: 126℃
• Appearance: /
• Density: 1.488
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.77±0.11(Predicted)
• CAS DataBase Reference: PYRIDINE-3-SULFONYL CHLORIDE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PYRIDINE-3-SULFONYL CHLORIDE HYDROCHLORIDE(16133-25-8)
• EPA Substance Registry System: PYRIDINE-3-SULFONYL CHLORIDE HYDROCHLORIDE(16133-25-8)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34-43
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 16133-25-8(Hazardous Substances Data)

Usage

Uses

3-pyridinesulfonyl Chloride is a reagent used in the synthesis of pyrimidine derivatives with anti-proliferative activity against negative breast cancer cells.

Synthetic route

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%

pyridine-3-sulfonyl chloride hydrochloride (42899-76-3) → Pyridine-3-sulfonyl chloride (16133-25-8)

Conditions	Yield
In chlorobenzene at 85℃; under 172.517 Torr;	92.9%
With sodium hydrogencarbonate In dichloromethane; water

pyridin-3-ylamine (462-08-8) → Pyridine-3-sulfonyl chloride (16133-25-8)

Conditions	Yield
Stage #1: pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water at -5 - 0℃; Large scale; Green chemistry; Stage #2: With thionyl chloride; sulphurous acid; copper(l) chloride In water at 0 - 4℃; for 1.5h; Concentration; Reagent/catalyst; Large scale; Green chemistry;	91%
Stage #1: pyridin-3-ylamine With hydrogenchloride; sodium tetrafluoroborate; sodium nitrite In water at 0 - 5℃; Stage #2: With thionyl chloride; copper(l) chloride In water at 0 - 5℃;	90.7%
Stage #1: pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water at -20℃; for 2h; Stage #2: With copper(II) choride dihydrate; sulfur dioxide In dichloromethane; water at -5 - 0℃; for 1h;	52.1%
Stage #1: pyridin-3-ylamine With hydrogenchloride In water at 30℃; Sandmeyer reaction; Stage #2: With sodium nitrite In water at -5 - 0℃; for 0.916667h; Sandmeyer reaction; Stage #3: With thionyl chloride; water; copper(l) chloride at -5 - 0℃; for 2.83333h; Sandmeyer reaction;	38.4%

pyridine-3-thiol (16133-26-9) → Pyridine-3-sulfonyl chloride (16133-25-8)

Conditions	Yield
With chlorine In water; acetic acid at 15 - 17℃; for 0.5h;	81%

3-Bromopyridine (626-55-1) → Pyridine-3-sulfonyl chloride (16133-25-8)

Conditions	Yield
Stage #1: 3-Bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With sulfur dioxide In tetrahydrofuran at -40℃; for 0.5h; Stage #3: With sulfuryl dichloride In tetrahydrofuran at -40 - 20℃;
Stage #1: 3-Bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 10℃; Inert atmosphere; Stage #2: With sulfuryl dichloride In tetrahydrofuran; toluene at -10 - 10℃;
Stage #1: 3-Bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 0.583333h; Inert atmosphere; Stage #2: With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In tetrahydrofuran at -40℃; for 1h; Inert atmosphere; Stage #3: With sulfuryl dichloride In tetrahydrofuran at -40 - 20℃; Inert atmosphere;

pyridine (110-86-1) → Pyridine-3-sulfonyl chloride (16133-25-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: fuming H2SO4; HgSO4 / 230 °C 2: PCl5 / 120 °C View Scheme
Multi-step reaction with 2 steps 1: fuming H2SO4; HgSO4 / 300 °C 2: PCl5 / 120 °C View Scheme

morpholine (110-91-8) + 3-pyridinesulfonic acid (636-73-7) → Pyridine-3-sulfonyl chloride (16133-25-8)

Conditions	Yield
With phosphorus pentachloride; triethylamine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; toluene

3-pyridinesulfonic acid (636-73-7) + phosphorus pentachloride (10026-13-8, 874483-75-7) → Pyridine-3-sulfonyl chloride (16133-25-8)

Conditions	Yield
With hydrogenchloride; trichlorophosphate In chloroform

3-pyridinesulfonic acid (636-73-7) → Pyridine-3-sulfonyl chloride (16133-25-8) + 5-[2-(Piperidin-4-yl)ethyl]thieno-[2,3-b]thiophene-2-N-[3-2(S)-(2-ethoxyethanesulfonylamino)propionic acid]carboxamide

Conditions	Yield
With phosphorus pentachloride In toluene	A 30.7 g (92%) B n/a

3,4-dihydro-2H-pyran (110-87-2) + N-(4-hydroxybutyl)pyridine-3-sulfonamide + 4-Aminobutanol (13325-10-5) → Pyridine-3-sulfonyl chloride (16133-25-8) + N-(4-(2-tetrahydropyranyloxy)butyl)pyridine-3-sulfonamide (173843-37-3)

Conditions	Yield
With p-toluenesulfonic acid monohydrate; triethylamine In dichloromethane; chloroform; ethyl acetate

Pyridine-3-sulfonyl chloride (16133-25-8) + 5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde (881674-60-8) → 1-(pyridin-3-ylsulfonyl)-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde (881677-15-2)

Conditions	Yield
Stage #1: 5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: Pyridine-3-sulfonyl chloride With 15-crown-5 In tetrahydrofuran at 0 - 20℃;	100%

Pyridine-3-sulfonyl chloride (16133-25-8) + (3-(tert-butyl)phenyl)methanamine (608515-16-8) → N-(3-tert-butylbenzyl)pyridin-3-ylsulfonamide (1313217-72-9)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	100%

Pyridine-3-sulfonyl chloride (16133-25-8) + N,N-Dimethyltrimethylsilylamine (2083-91-2) → N,N-Dimethyl-3-pyridinsulfonsaeureamid

Conditions	Yield
In acetonitrile for 1h; Reflux; Inert atmosphere;	99%

8-amino quinoline (578-66-5) + Pyridine-3-sulfonyl chloride (16133-25-8) → N-(quinolin-8-yl)pyridine-3-sulfonamide (1136429-51-0)

Conditions	Yield
With pyridine at 25℃;	99%
With pyridine at 130℃; for 0.5h;	82%

Pyridine-3-sulfonyl chloride (16133-25-8) + 5-[(3,4-dichlorophenyl)methylamino]-1-(4-piperidyl)-6H-pyrazolo[4,3-d]pyrimidin-7-one → 5-((3,4-dichlorobenzyl)amino)-1-(1-(pyridin-3-ylsulfonyl)piperidin-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one hydrochloride

Conditions	Yield
Stage #1: Pyridine-3-sulfonyl chloride; 5-[(3,4-dichlorophenyl)methylamino]-1-(4-piperidyl)-6H-pyrazolo[4,3-d]pyrimidin-7-one With triethylamine In dichloromethane at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride	98.51%

1-ethenyl-2-pyrrolidinone (88-12-0) + Pyridine-3-sulfonyl chloride (16133-25-8) → (E)-1-(2-(pyridin-3-ylsulfonyl)vinyl)pyrrolidin-2-one (1429936-66-2)

Conditions	Yield
With sodium dihydrogenphosphate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In acetonitrile at 20℃; for 8h; Inert atmosphere; Irradiation;	98%

Pyridine-3-sulfonyl chloride (16133-25-8) + Cyclopropylamine (765-30-0) → N-cyclopropylpyridine-3-sulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 22h; Schlenk technique; Inert atmosphere;	98%

Pyridine-3-sulfonyl chloride (16133-25-8) + tert-butyl {[5-(2-chloropyridin-3-yl)-4-fluoro-1H-pyrrol-3-yl]methyl}methylcarbamate (1055306-84-7) → tert-butyl {[5-(2-chloropyridin-3-yl)-4-fluoro-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (1055306-93-8)

Conditions	Yield
With 15-crown-5; sodium hydride In tetrahydrofuran at 0℃; for 0.25h;	97%

Pyridine-3-sulfonyl chloride (16133-25-8) + 2-Iodophenol (533-58-4) → 2-iodophenyl 3-pyridinesulfonate

Conditions	Yield
With pyridine; dmap at 20℃; for 72h;	97%

Pyridine-3-sulfonyl chloride (16133-25-8) + N,N-diethyl-1,3-benzenediamine (26513-20-2) → C15H19N3O2S (870274-40-1)

Conditions	Yield
Stage #1: Pyridine-3-sulfonyl chloride; N,N-diethyl-1,3-benzenediamine In 1,2-dichloro-ethane at 20 - 40℃; Stage #2: With sodium hydroxide In dichloromethane; water pH=7;	96%

Pyridine-3-sulfonyl chloride (16133-25-8) + 1-(piperidin-4-ylmethyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-1H-indole → 1-((1-(pyridin-3-ylsulfonyl)piperidin-4-yl)methyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-1H-indole

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h;	96%

Pyridine-3-sulfonyl chloride (16133-25-8) + L-prolyl-L-O-(1-pyrrolidinylcarbonyl)tyrosine methyl ester (425388-80-3) → N-(3-pyridinesulfonyl)-L-prolyl-L-O-(1-pyrrolidinylcarbonyl)tyrosine methyl ester

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	96%

Pyridine-3-sulfonyl chloride (16133-25-8) + methyl 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate (1240949-59-0) → C17H13FN2O4S

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h;	95.8%

1-ethylpyrrolidine (7335-06-0) + Pyridine-3-sulfonyl chloride (16133-25-8) → 3-(pyrrolidin-1-ylsulfonyl)pyridine (26103-51-5)

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In tetrahydrofuran; decane at 80℃; for 4h; Sealed tube; chemoselective reaction;	95%

Pyridine-3-sulfonyl chloride (16133-25-8) + n-Octylamine (111-86-4) → N-octylpyridine-3-sulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	95%

Pyridine-3-sulfonyl chloride (16133-25-8) + C9H6FN3O → C14H9FN4O3S

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h;	94.3%

methyl 4-[(2-amino-5-(trifluoromethyl)phenoxy)methyl]benzoate (907587-49-9) + Pyridine-3-sulfonyl chloride (16133-25-8) → methyl 4-{[2-[(pyridin-3-ylsulfonyl)amino]-5-(trifluoromethyl)phenoxy]methyl}benzoate (909896-93-1)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 4h;	94%

C15H29N7 + Pyridine-3-sulfonyl chloride (16133-25-8) → N1-[4-([4,6-di(ethylamino)-1,3,5-triazin-2-yl]aminomethyl)cyclohexyl]methyl-3-pyridinesulfonamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane	94%

Pyridine-3-sulfonyl chloride (16133-25-8) + aniline (62-53-3) → pyridine-3-sulfonic acid phenylamide (103860-56-6)

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 90℃; for 3h;	94%
With sodium hydrogencarbonate In 1,4-dioxane at 90℃; for 3h;	94%
With triethylamine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;	92%
Stage #1: Pyridine-3-sulfonyl chloride With pyridine In dichloromethane at 20℃; for 0.333333h; Stage #2: aniline In dichloromethane at 20℃; for 24h;	91.4%

Pyridine-3-sulfonyl chloride (16133-25-8) + 5-(2-fluorophenyl)-1H-pyrrole-3-carboxaldehyde (881674-56-2) → 5‐(2-fluorophenyl)‐1‐(pyridine-3-sulfonyl)-1H-pyrrole-3-carbaldehyde (881677-11-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h;	93.8%
With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 50℃; for 2h;	90.6%
With dmap; triethylamine In acetonitrile at 45℃; for 1.5h;	88.7%

Pyridine-3-sulfonyl chloride (16133-25-8) + tert-butyl N-{[5-(2-fluorophenyl)-1H-pyrrol-3-yl]methyl}-N-methylcarbamate → ((5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamic acid tert-butyl ester

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Solvent; Cooling with ice;	93.5%
Stage #1: tert-butyl N-{[5-(2-fluorophenyl)-1H-pyrrol-3-yl]methyl}-N-methylcarbamate With sodium hydride In diethyl ether at 30 - 35℃; Inert atmosphere; Cooling with ice; Stage #2: Pyridine-3-sulfonyl chloride In diethyl ether at 0 - 60℃; for 0.166667h; Solvent; Temperature;

Pyridine-3-sulfonyl chloride (16133-25-8) + 2,4-difluoro-3-ethynylaniline → N-(3-ethynyl-2,4-difluborophenyl)pyridine-3-ylsulfonamide

Conditions	Yield
With pyridine In dichloromethane at 20℃;	93%

Pyridine-3-sulfonyl chloride (16133-25-8) + 2-(2-fluorophenyl)-4-methyl-1H-pyrrole (1428932-17-5) → 5-(2-fluorophenyl)-3-methyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole

Conditions	Yield
With triethylamine In dichloromethane; toluene at 25℃; for 1h; Reagent/catalyst; Solvent; Temperature;	92.8%
With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; for 4h; Inert atmosphere;	87%

2-aminopyridine (504-29-0) + Pyridine-3-sulfonyl chloride (16133-25-8) → N-(2-pyridyl)-3-pyridylsulfonamide

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 4h;	92%
With pyridine

Pyridine-3-sulfonyl chloride (16133-25-8) + 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile (1240948-77-9) → 5-(2-fluorophenyl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrole-3-carbonitrile

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 10 - 30℃; for 3h;	91.5%
With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 30℃; for 2h;	90.5%
With dmap; N-ethyl-N,N-diisopropylamine

Pyridine-3-sulfonyl chloride (16133-25-8) + 5-(2-bromophenyl)-1H-pyrrole-3-carbaldehyde (928324-88-3) → 5-(2-bromophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (928324-94-1)

Conditions	Yield
Stage #1: 5-(2-bromophenyl)-1H-pyrrole-3-carbaldehyde With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: Pyridine-3-sulfonyl chloride With 15-crown-5 In tetrahydrofuran at 0 - 20℃;	91%

Pyridine-3-sulfonyl chloride (16133-25-8) + (4-(difluoromethoxy)phenyl)methanamine (177842-14-7) → N-(4-difluoromethoxybenzyl)pyridin-3-ylsulfonamide (1023230-97-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	91%

Upstream product

• 636-73-7 3-pyridinesulfonic acid 
• 10026-13-8 phosphorus pentachloride 
• 462-08-8 pyridin-3-ylamine 
• 42899-76-3 pyridine-3-sulfonyl chloride hydrochloride 
• 16133-26-9 pyridine-3-thiol 
• 110-91-8 morpholine 
• 110-86-1 pyridine 
• 626-55-1 3-Bromopyridine 
• 110-87-2 3,4-dihydro-2H-pyran 
• 13325-10-5 4-Aminobutanol 

Downstream Products

• 111664-38-1 pyridine-3-sulfonic acid-[3-(6-ethoxy-[2]quinolyl)-anilide] 
• 88842-76-6 pyridine-3-sulfonic acid-(3-benzo[f]quinolin-3-yl-anilide) 
• 88842-77-7 pyridine-3-sulfonic acid-(4-benzo[f]quinolin-3-yl-anilide) 
• 110936-40-8 pyridine-3-sulfonic acid-[4-(6-methoxy-[2]quinolyl)-anilide] 
• 111664-05-2 pyridine-3-sulfonic acid-[4-(6-ethoxy-[2]quinolyl)-anilide] 
• 110936-65-7 pyridine-3-sulfonic acid-[3-(6-methoxy-[2]quinolyl)-anilide] 
• 4810-42-8 N,N-diethylpyridine-3-sulfonamide 
• 2922-45-4 3-pyridinesulfonamide 
• 65227-53-4 pyridine-3-sulfonohydrazide 
• 263843-26-1 pyridine-3-sulfonic acid 5-tert-butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenyl ester 
• 263843-18-1 toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(3-pyridinesulfonylamino)-5-methylphenyl] ester 
• 820216-57-7 pyridine-3-sulfonic acid 3-(2-{2-(tert-butyl-dimethyl-silanyloxy)-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yl ester 
• 262430-07-9 N₃-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-3-pyridinesulfonamide 
• 737799-50-7 (R)-5,5-dimethyl-3-(pyridin-3-ylsulfonyl)thiazolidine-4-carboxylic acid 

Relevant articles and documents

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