53054-76-5

Basic information

• Product Name: 4-Pyridineethanesulfonic acid
• Synonyms: PYRID-4-YLETHYLSULFONIC ACID;PYRIDIN-4-YLETHANESULPHONIC ACID;PESA;LABOTEST-BB LT00233123;4PYESA;4-PYRIDYL-2-ETHYL SULFONIC ACID;4-PYRIDINEETHENESULFONIC ACID;4-PYRIDINEETHANESULFONIC ACID
• CAS NO: 53054-76-5
• Molecular Formula: C₇H₉NO₃S
• Molecular Weight: 187.22
• EINECS: 258-331-3
• Mol File: 53054-76-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 297-299 °C (dec.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: Off-White to light yellow Powder
• Density: 1.397 g/cm³
• Refractive Index: 1.573
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 1.31±0.50(Predicted)
• BRN: 136690
• CAS DataBase Reference: 4-Pyridineethanesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pyridineethanesulfonic acid(53054-76-5)
• EPA Substance Registry System: 4-Pyridineethanesulfonic acid(53054-76-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• RIDADR: UN 2585 8/PG 3
• WGK Germany: 2
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 53054-76-5(Hazardous Substances Data)

Usage

Uses

2-(4-Pyridyl)ethanesulfonic acid was used in the preparation of benzyldimethyltetradecyl ammoniumchloride dihydrate solution.

General Description

2-(4-Pyridyl)ethanesulfonic acid is the sulfonated substrate for alkanesulfonate monooxygenase isolated from Escherichia coli.

InChI:InChI=1/C7H9NO3S/c9-12(10,11)6-3-7-1-4-8-5-2-7/h1-2,4-5H,3,6H2,(H,9,10,11)

Synthetic route

4-vinylpyridine (100-43-6) → 2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5)

Conditions	Yield
With sodium hydrogensulfite In water at 20℃;	90%
With water; sodium hydrogensulfite
With ethanol; sulfur dioxide

4-vinylpyridine (100-43-6) + water (7732-18-5) + sodium hydrogensulfite → 2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5)

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) + water (7732-18-5) + silver(l) oxide (20667-12-3) → [μ3-2-(4-pyridyl)ethanesulfonato-N,O,O']-aqua-silver(I)

Conditions	Yield
In methanol; water mixt. of 2-(4-pyridyl)ethanesulfonic acid and Ag2O in CH3OH/H2O heated to 40°C for 1 h with vigorously stirring; cooled; filtered; crystals were obtained from mother liquor by slow evapn. at room temp. for several ds; elem. anal.;	85%

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) → 2-(pyridin-4-yl)ethanesulfonyl chloride hydrochloride

Conditions	Yield
With phosphorus pentachloride In trichlorophosphate at 0 - 60℃; for 2h;	78%
With trichlorophosphate In tetrachloromethane

2,4,6-triamino-s-triazine (108-78-1) + 2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) + silver perchlorate → melamine-[2-(4-pyridyl)ethanesulfonato-N]-silver(I) (736149-73-8)

Conditions	Yield
In methanol mixt. of 2-(4-pyridyl)ethanesulfonic acid, melamine and AgClO4 in CH3OH heated to 40°C for 1 h with vigorously stirring; cooled; filtered; ppt. dissolved in DMSO; crystals were obtained by slow evapn. at room temp. for several ds; elem. anal.;	62%

1,10-Phenanthroline (66-71-7) + 2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) + copper(II) nitrate trihydrate → diaqua(1,10-phenanthroline)copper(II) sulfate

Conditions	Yield
In methanol; water at 130℃; for 72h; Autoclave;	60%

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) + 4-hydroxy-benzaldehyde (123-08-0) → 3-(4-Hydroxyphenyl)-2-(4-pyridinio)-2-propenesulfonate (111260-13-0)

Conditions	Yield
With piperidine In dimethyl sulfoxide at 110℃; for 12h;	5%

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) + 4-methoxy-benzaldehyde (123-11-5) → 3-(4-Methoxyphenyl)-2-(4-pyridinio)-2-propenesulfonate (111260-14-1)

Conditions	Yield
With piperidine In dimethyl sulfoxide	5%

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) → N-3-(4-piperidineethanesulfonyl)-nipecotyl-3-aminopropionic acid.HCl

Conditions	Yield
With 4-methyl-morpholine; hydrogenchloride; hydrogen; benzyl chloroformate; platinum(IV) oxide

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) + Zn(ClO4)2·2H2O + water (7732-18-5) → tetraaquabis[2-(4-pyridyl)ethanesulfonato-N]zinc(II) (292859-25-7)

Conditions	Yield
With pyridine; water 2-(4-pyridyl)ethanesulfonic acid and Zn(ClO4)2*2H2O added to water and pyridine; soln. was evapd. at room temp. for a few days;

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) + benzyl chloroformate (501-53-1) → 2-{1-[(benzyloxy)carbonyl]piperidin-4-yl}ethanesulfonic acid (198959-43-2)

Conditions	Yield
Stage #1: 2-(pyridin-4-yl)-ethanesulfonic acid With ammonia; hydrogen; 5% rhodium on activated aluminium oxide In water at 30℃; under 3800.26 Torr; Stage #2: benzyl chloroformate In water at 0 - 20℃; for 1h;

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) → (R)-1-{3-(3,5-difluorophenyl)-3-[4-(methylsulfonyl)phenyl]propyl}-4-[2-(piperidin-1-ylsulfonyl)ethyl]piperidine hydrochloride

Conditions

Yield

Multi-step reaction with 5 steps 1.1: ammonia; hydrogen / 5% rhodium on activated aluminium oxide / water / 30 °C / 3800.26 Torr 1.2: 1 h / 0 - 20 °C 2.1: thionyl chloride / 4 h / Heating / reflux 3.1: dichloromethane / 2 h / 5 - 20 °C 4.1: hydrogenchloride; hydrogen / 5%-palladium/activated carbon / ethanol; water / 24 h / 20 °C 5.1: potassium carbonate / acetonitrile / 6 h / Heating / reflux View Scheme

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) → 2-{1-[(benzyloxy)carbonyl]piperidin-4-yl}ethanesulfonyl chloride (184965-14-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ammonia; hydrogen / 5% rhodium on activated aluminium oxide / water / 30 °C / 3800.26 Torr 1.2: 1 h / 0 - 20 °C 2.1: thionyl chloride / 4 h / Heating / reflux View Scheme

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) → benzyl 4-[2-(piperidin-1-ylsulfonyl)ethyl]piperidine-1-carboxylate (833491-17-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonia; hydrogen / 5% rhodium on activated aluminium oxide / water / 30 °C / 3800.26 Torr 1.2: 1 h / 0 - 20 °C 2.1: thionyl chloride / 4 h / Heating / reflux 3.1: dichloromethane / 2 h / 5 - 20 °C View Scheme

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) → 1-[(2-piperidin-4-ylethyl)sulfonyl]piperidine hydrochloride (833491-18-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ammonia; hydrogen / 5% rhodium on activated aluminium oxide / water / 30 °C / 3800.26 Torr 1.2: 1 h / 0 - 20 °C 2.1: thionyl chloride / 4 h / Heating / reflux 3.1: dichloromethane / 2 h / 5 - 20 °C 4.1: hydrogenchloride; hydrogen / 5%-palladium/activated carbon / ethanol; water / 24 h / 20 °C View Scheme

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) → 2-(pyridin-4-yl)ethanesulfonyl chloride

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide for 0.5h; Reflux;

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) → 2-(pyridin-4-yl)ethanesulfonamide

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / 0.5 h / Reflux 2: ammonium hydroxide / dichloromethane / 12 h / 0 - 20 °C View Scheme

2-(pyridin-4-yl)-ethanesulfonic acid (53054-76-5) + terephthalic acid (100-21-0) + chromium(III) chloride hexahydrate + hydrogen fluoride (7664-39-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → Cr6O2F2(12+)*6C8H4O4(2-)*5.6C3H7NO*1.45C7H9NO3S

Conditions	Yield
at 210℃; for 24h; Autoclave;

Upstream product

• 100-43-6 4-vinylpyridine 
• 7732-18-5 water 

Downstream Products

• 252670-82-9 2-(pyridin-4-yl)ethanesulfonyl chloride 
• 833491-17-1 benzyl 4-[2-(piperidin-1-ylsulfonyl)ethyl]piperidine-1-carboxylate 
• 184965-14-8 2-{1-[(benzyloxy)carbonyl]piperidin-4-yl}ethanesulfonyl chloride 
• 198959-43-2 2-{1-[(benzyloxy)carbonyl]piperidin-4-yl}ethanesulfonic acid 
• 81705-92-2 2-(pyridin-4-yl)ethanesulfonyl chloride hydrochloride 
• 111260-14-1 3-(4-Methoxyphenyl)-2-(4-pyridinio)-2-propenesulfonate 
• 111260-13-0 3-(4-Hydroxyphenyl)-2-(4-pyridinio)-2-propenesulfonate 

Relevant articles and documents

COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH APJ RECEPTOR ACTIVITY

This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt and/or hydrate and/or prodrug of the compound) that modulate (e.g., agonize) the apelin receptor (also referred to herein as the APJ receptor; gene symbol "APLNR"). This disclosure also features compositions containing the same as well as other methods of using and making the same. The chemical entities are useful, e.g., for treating a subject (e.g., a human) having a disease, disorder, or condition in which a decrease in APJ receptor activity (e.g., repressed or impaired APJ receptor signaling; e.g., repressed or impaired apelin-APJ receptor signaling) or downregulation of endogenous apelin contributes to the pathology and/or symptoms and/or progression of the disease, disorder, or condition. Non-limiting examples of such diseases, disorders, or conditions include: (i) cardiovascular disease; (ii) metabolic disorders; (iii) diseases, disorders, and conditions associated with vascular pathology; and (iv) organ failure; (v) diseases, disorders, and conditions associated with infections (e.g., microbial infections); and (vi) diseases, disorders, or conditions that are sequela or comorbid with any of the foregoing or any disclosed herein. More particular non-limiting examples of such diseases, disorders, or conditions include pulmonary hypertension (e.g., PAH); heart failure; type II diabetes; renal failure; sepsis; and systemic hypertension.