pyridine-3-sulfonyl chloride

Bezeichnung:pyridine-3-sulfonyl chloride

CAS-Nr16133-25-8

Englisch Name:pyridine-3-sulfonyl chloride

CBNumberCB5153121

SummenformelC5H4ClNO2S

Molgewicht177.61

MOL-Datei16133-25-8.mol

pyridine-3-sulfonyl chloride physikalisch-chemischer Eigenschaften

Schmelzpunkt	144 °C
Siedepunkt	284℃
Dichte	1.488
Brechungsindex	n20/D 1.556
Flammpunkt	126℃
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit	Chloroform (Sparingly), Methanol (Slightly)
Aggregatzustand	liquid
pka	-1.77±0.11(Predicted)
Farbe	Colourless to light yellow
Stabilität	Moisture Sensitive
InChI	InChI=1S/C5H4ClNO2S/c6-10(8,9)5-2-1-3-7-4-5/h1-4H
InChIKey	CDRNYKLYADJTMN-UHFFFAOYSA-N
SMILES	C1=NC=CC=C1S(Cl)(=O)=O
LogP	1.75
CAS Datenbank	16133-25-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,C
R-Sätze:	34-43
S-Sätze:	26-36/37/39-45
RIDADR	3261
WGK Germany	3
HazardClass	IRRITANT
PackingGroup	Ⅲ
HS Code	2933399990
Speicherklasse	8A - Combustible corrosive hazardous materials
Hazard Classifications	Skin Corr. 1B Skin Sens. 1

Gefahreninformationscode (GHS)

pyridine-3-sulfonyl chloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R34:Verursacht Verätzungen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
It is a colorless, transparent liquid. It is extremely unstable when in contact with water and is easily hydrolyzed to generate pyridine-3-sulfonic acid and hydrochloric acid, which makes it lose its reactivity.
Verwenden
3-pyridinesulfonyl Chloride is a reagent used in the synthesis of pyrimidine derivatives with anti-proliferative activity against negative breast cancer cells.
Application
Pyridine-3-sulfonyl chloride is an essential medical intermediate and is widely applied to the synthesis of medicines, wherein the pyridine-3-sulfonyl chloride is mainly used for preparing TAK-438 (vonoprazan fumarate), which is a novel orally active potassium-competitive acid blocker, developed as an antisecretory drug.
Toxikologie
Pyridine-3-sulfonyl chloride causes burns of eyes, skin and mucous membranes. Contact with water liberates toxic gas.
Synthese
Add thionyl chloride to the water, cool to about 0-5°C, and add cuprous chloride. Fluoboric acid diazonium salt was added to the solution and reacted at 0-5°C overnight. The reaction solution was extracted with dichloromethane, combining the organic layers. The organic layer was washed once with saturated aqueous sodium bicarbonate solution, once with water, and finally once with saturated brine. The product was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated to remove methylene chloride to obtain the product pyridine-3-sulfonyl chloride with a yield of 90.7%.
Einzelnachweise
[1] Journal of the American Chemical Society, 1992, vol. 114, # 12, p. 4889 - 4898
[2] Patent: US2006/217387, 2006, A1. Location in patent: Page/Page column 25
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 13, p. 2409 - 2421
[4] Patent: CN106432067, 2017, A. Location in patent: Paragraph 0090
[5] Patent: WO2016/90317, 2016, A1. Location in patent: Page/Page column 73

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