ISOQUINOLINE-5-SULFONYL CHLORIDE Chemical Properties

Melting point:

173-183°C

Boiling point:

371.2±17.0 °C(Predicted)

Density 

1.483

Flash point:

178.3℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Sparingly, Heated)

form 

Solid

pka

3.09±0.13(Predicted)

color 

White to Off-White

Stability:

Moisture Sensitive

CAS DataBase Reference

84468-15-5(CAS DataBase Reference)

Safety Information

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37

HS Code 

29334900

ISOQUINOLINE-5-SULFONYL CHLORIDE Usage And Synthesis

Chemical Properties

Colourless Crystalline Solid

Synthesis

The general procedure for the synthesis of isoquinoline-5-sulfonyl chloride from 5-isoquinolinesulfonic acid was as follows: 5-isoquinolinesulfonic acid was placed in a round-bottomed flask, 6 mL of thionyl chloride and 1 drop of N,N-dimethylformamide (DMF) were added, and the reaction was carried out at reflux for 3 hours. Upon completion of the reaction, the excess thionyl chloride was removed using a rotary evaporator. Dichloromethane (DCM) was added to the residual solid and the solid product was collected by filtration. The solid was washed three times with DCM and subsequently dried in a vacuum oven to give a white solid intermediate 2 (1 g, 91.9% yield). Intermediate 2 (130.00 mg, 571.01 μmol) was slowly added to a solution of DCM (6 mL) containing ethylenediamine (381.30 μL, 5.71 mmol) under ice-bath conditions. After removing the ice bath, the mixture was allowed to react for 3 h at room temperature. Upon completion of the reaction, the mixture was washed with water to remove the remaining ethylenediamine. The organic phase was removed using a rotary evaporator and the residue was recrystallized by ether to give brown solid 3 (91.8 mg, 60% yield).

References

[1] Patent: US2017/37050, 2017, A1. Location in patent: Paragraph 0064; 0068; 0069
[2] Patent: CN106279136, 2017, A. Location in patent: Paragraph 0022
[3] Patent: US5891909, 1999, A
[4] Patent: US6235778, 2001, B1
[5] Patent: EP906091, 2006, B1. Location in patent: Page/Page column 48

ISOQUINOLINE-5-SULFONYL CHLORIDE(84468-15-5)Related Product Information

• Isoquinoline-5-sulphonyl chloride hydrochloride
• p-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolyl)ethyl]benzenesulphonamide
• Tosyl chloride
• Sulfuryl chloride
• ISOQUINOLINE-8-CARBOXYLIC ACID
• 7-isoquinolinecarboxylic acid
• 1-ISOQUINOLINEMETHANOL
• ISOQUINOLINE-1-CARBALDEHYDE
• ISOQUINOLINE-1-CARBOXYLIC ACID METHYL ESTER
• Isoquinoline-3-carboxylic acid
• ISOQUINOLIN-3-AMINE
• Isoquinoline-3-carboxiMidaMide hydrochloride
• ISOQUINOLINE-4-BORONIC ACID HYDROCHLORIDE
• 8-isoquinolinyl-boronic acid
• Isoquinoline-7-carboxaMide
• C-ISOQUINOLIN-4-YL-METHYLAMINE
• ISOQUINOLINE-5-CARBOXYLIC ACID
• Methyl 3-isoquinolinecarboxylate