8-Quinolinesulfonyl chloride Chemical Properties

Melting point:

126-129 °C(lit.)

Boiling point:

306°C

Density 

1.483±0.06 g/cm3(Predicted)

Flash point:

306°C

storage temp. 

Inert atmosphere,2-8°C

solubility 

methanol: soluble10mg/mL, clear, colorless to light yellow

pka

0?+-.0.17(Predicted)

form 

powder to crystal

color 

White to Orange to Green

Sensitive 

Moisture Sensitive

BRN 

156347

InChI

InChI=1S/C9H6ClNO2S/c10-14(12,13)8-5-1-3-7-4-2-6-11-9(7)8/h1-6H

InChIKey

JUYUYCIJACTHMK-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2S(Cl)(=O)=O)C=CC=1

CAS DataBase Reference

18704-37-5(CAS DataBase Reference)

NIST Chemistry Reference

Sulfonyl chloride, 8-quinoline-(18704-37-5)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45-27

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

RTECS 

VC2830000

F 

3-10-21

HazardClass 

8

PackingGroup 

III

HS Code 

29334990

MSDS

• Language:English Provider:8-Quinolinesulfonyl chloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

8-Quinolinesulfonyl chloride Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

8-Quinolinesulfonyl chloride was used as a coupling reagent in oligonucleotide synthesis. It was also used in the synthesis of olefins from secondary esters at moderate temperature

General Description

8-Quinolinesulfonyl chloride reacts with aromatic/heterocyclic sulfonamides containing a free amino, imino, hydrazino or hydroxyl group to form water-soluble compounds.

Synthesis

The general procedure for the synthesis of quinoline-8-sulfonyl chloride from quinoline-8-sulfonic acid is as follows: chlorosulfonic acid (6.0 g, 51.5 mmol) was added to a reaction vessel fitted with a magnetic stirrer under nitrogen protection. Quinoline (1.0 g, 7.74 mmol) was slowly added under cooling in an ice bath. Subsequently, the reaction system was gradually warmed to 140 °C and the reaction was continuously stirred at this temperature for 10 hours. Upon completion of the reaction, the system was cooled to 40 °C and thionyl chloride (2.0 g, 16.0 mmol) was added dropwise. Then, the reaction temperature was raised to 70 °C and the reaction continued to be stirred for 4 hours. At the end of the reaction, the reaction system was allowed to cool naturally to room temperature, and the reaction solution was slowly poured into ice water, which immediately precipitated a solid. After stirring the mixture for 30 min, the solid product was collected by filtration and dried under vacuum to give quinoline-8-sulfonyl chloride (1.7 g, 99% yield). Mass spectrometry analysis showed m/z: 228.0 (M+1).

References

[1] Patent: WO2018/156297, 2018, A1. Location in patent: Paragraph 0101; 0114; 0115; 0116; 0117
[2] Synthesis, 2004, # 18, p. 2999 - 3004
[3] Chemische Berichte, 1908, vol. 41, p. 942
[4] Chemische Berichte, 1886, vol. 19, p. 925

8-Quinolinesulfonyl chloride(18704-37-5)Related Product Information

• Oxalyl chloride
• Sulfuryl chloride
• Quinoline Yellow
• Ethanesulfonyl chloride
• Zinc chloride
• 3-Methyl-8-quinolinesulphonyl chloride
• N-Acetylsulfanilyl chloride
• Sodium chloride
• Benzenesulfonyl chloride
• Calcium chloride
• Thionyl chloride
• 4-Nitrobenzenesulfonyl chloride
• Quinoline
• Ammonium chloride
• Choline chloride
• Tosyl chloride
• Potassium chloride
• 3-QUINOLINEBORONIC ACID HYDROCHLORIDE