5-Isoquinolinesulfonic acid Chemical Properties

Melting point:

>300 °C (lit.)

Density 

1.4048 (rough estimate)

refractive index 

1.5364 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

-0.98±0.40(Predicted)

form 

Solid

color 

White to Almost white

InChI

InChI=1S/C9H7NO3S/c11-14(12,13)9-3-1-2-7-6-10-5-4-8(7)9/h1-6H,(H,11,12,13)

InChIKey

YFMJTLUPSMCTOQ-UHFFFAOYSA-N

SMILES

C1C2=C(C(S(O)(=O)=O)=CC=C2)C=CN=1

CAS DataBase Reference

27655-40-9(CAS DataBase Reference)

EPA Substance Registry System

5-Isoquinolinesulfonic acid (27655-40-9)

Safety Information

Hazard Codes 

T,C,Xi

Risk Statements 

49-23-34-24-36/38

Safety Statements 

53-26-27-36/37/39-45

RIDADR 

UN 2585 8/PG 3

WGK Germany 

1

Hazard Note 

Toxic

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29334900

MSDS

• Language:English Provider:5-Isoquinolinesulfonic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

5-Isoquinolinesulfonic acid Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

5-Isoquinolinesulfonic acid was used in the synthesis of conjugates of oligoarginine peptides.

Synthesis

The general procedure for the synthesis of 5-isoquinolinesulfonic acid from isoquinoline-5-sulfonyl chloride hydrochloride was as follows: the synthesis of compound 3i was carried out according to the method reported in the literature [56,57]. The procedure was as follows: 5-isoquinolinesulfonic acid (2.10 g, 10 mmol), 25 mL of thionyl chloride, and 1 mL of dimethylformamide were added to a 100 mL round-bottomed flask, and the mixture was refluxed for 1 hour. Upon completion of the reaction, the remaining thionyl chloride was removed by rotary evaporation, and the residue was suspended in dichloromethane, filtered, and washed with dichloromethane (2 x 25 mL). The precipitate was collected and dried under vacuum to give the crude isoquinoline-5-sulfinyl chloride hydrochloride in 85% yield (2.25 g). Next, isoquinoline-5-sulfonyl chloride hydrochloride (2.0 g, 7.6 mmol) and 20 mL of ice-cold deionized water were added to another 100 mL round bottom flask. The mixture was slowly added to an equimolar amount of sodium bicarbonate (0.64 g) and the resulting solution was extracted twice with dichloromethane (2 x 20 mL). The organic layers were combined, dried with anhydrous sodium sulfate, and then added dropwise to 25 mL of dichloromethane solution containing ethylenediamine (1.37 g, 22.8 mmol) at 0°C. The reaction was continued with stirring at room temperature for 1 h. The reaction was subsequently washed with deionized water to remove excess ethylenediamine and finally the solvent was evaporated. The residue was recrystallized from ethanol to give pure compound 3i in 55% yield.

References

[1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 18, p. 5694 - 5706

5-Isoquinolinesulfonic acid(27655-40-9)Related Product Information

• Taurine
• Ethyl 2-(Chlorosulfonyl)acetate
• 5,6,7,8-TETRAHYDROISOQUINOLINE
• 1-DODECANESULFONIC ACID SODIUM SALT
• Sulfamic acid
• Isoquinoline
• p-Toluenesulfonic acid
• Folic acid
• Glycine
• QUINOLINE-8-SULFONIC ACID
• Isomalt
• ISOQUINOLINE-5-SULFONYL CHLORIDE
• Fasudil Impurity 21
• 1-(p-Toluenesulfonyl)hoMopiperazine, 95%
• 1,4-ditosyl-1,4-diazepane
• Fasudil Impurity 24
• Fasudil Impurity 10
• Fasudil diMer