3-Cyanobenzene-1-sulfonyl chloride

Bezeichnung:3-Cyanobenzene-1-sulfonyl chloride

CAS-Nr56542-67-7

Englisch Name:3-Cyanobenzene-1-sulfonyl chloride

CBNumberCB1126817

SummenformelC7H4ClNO2S

Molgewicht201.63

MOL-Datei56542-67-7.mol

3-Cyanobenzene-1-sulfonyl chloride physikalisch-chemischer Eigenschaften

Schmelzpunkt	49-53 °C (lit.)
Siedepunkt	148 °C
Dichte	1.53±0.1 g/cm3(Predicted)
Flammpunkt	>230 °F
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Aggregatzustand	powder to crystal
Farbe	White to Light yellow to Dark green
Sensitive	Moistute Sensitive
BRN	2832925
InChI	1S/C7H4ClNO2S/c8-12(10,11)7-3-1-2-6(4-7)5-9/h1-4H
InChIKey	BHNRGBRMCNHNQD-UHFFFAOYSA-N
SMILES	ClS(=O)(=O)c1cccc(c1)C#N
CAS Datenbank	56542-67-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	C
R-Sätze:	34-43-20/21/22
S-Sätze:	26-36/37/39-45
RIDADR	UN 3261 8/PG 3
WGK Germany	3
Hazard Note	Corrosive
HazardClass	8
PackingGroup	III
HS Code	29269090
Speicherklasse	8A - Combustible corrosive hazardous materials
Hazard Classifications	Skin Corr. 1B Skin Sens. 1

Gefahreninformationscode (GHS)

3-Cyanobenzene-1-sulfonyl chloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R34:Verursacht Verätzungen.
R43:Sensibilisierung durch Hautkontakt möglich.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
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.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Verwenden
A benzenesulfonamide derivative as potential kinase inhibitors.
Synthese

2237-30-1

56542-67-7

General procedure for the synthesis of 3-cyanobenzenesulfonyl chloride from 3-aminobenzonitrile: 3-aminobenzonitrile (2.5 g, 21 mmol) was dissolved in concentrated hydrochloric acid. The mixture of hydrochloric acid (20 mL) and water (20 mL) was cooled to 0 °C and a solution of sodium nitrite (1.5 g, 22 mmol) in water (5 mL) was added slowly and dropwise. The reaction mixture was stirred at 0 °C for 10 min to ensure complete formation of the diazonium salt. In another flask, copper (I) chloride (0.2 g) was added to a solution of acetic acid (25 mL) pre-saturated with sulfur dioxide and stirred at 0°C for 10 minutes. This solution was slowly added dropwise to the above diazonium salt solution, kept at 0°C and stirred for 1 hour. After completion of the reaction, the mixture was poured into ice water and the product was extracted with tert-butyl methyl ether. The organic layers were combined and washed sequentially with water and brine. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% ethyl acetate in petroleum ether solution) to give pure 3-cyanobenzenesulfonyl chloride (1.9 g, 45% yield) as an off-white solid.1H NMR (300 MHz, CDCl3) δ 8.35 (t, J=1.5 Hz, 1H), 8.31-8.27 (m, 1H), and 8.06-8.02 (m, 1H), 7.82 (t, J=7.9Hz, 1H).
Einzelnachweise
[1] Collection of Czechoslovak Chemical Communications, 1999, vol. 64, # 11, p. 1833 - 1848
[2] Patent: EP2533783, 2015, B1. Location in patent: Paragraph 0335-0336
[3] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 5, p. 1182 - 1192
[4] Patent: US2002/128480, 2002, A1
[5] Patent: EP1258252, 2002, A1

3-Cyanobenzene-1-sulfonyl chloride Upstream-Materialien And Downstream Produkte

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