Isoquinoline-5-sulphonyl chloride hydrochloride Chemical Properties

Melting point:

173-183°C

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO (Sparingly, Heated)

form 

solid

color 

White

Stability:

Moisture Sensitive; Store in Freezer

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

HS Code 

29334900

Isoquinoline-5-sulphonyl chloride hydrochloride Usage And Synthesis

Chemical Properties

White Solid

Uses

Isoquinoline-5-sulfonyl Chloride, Hydrochloride (cas# 105627-79-0) is a compound useful in organic synthesis.

Synthesis

Anhydrous DMF (1.5 mL) was added slowly and dropwise to the suspension formed by stirring 5-isoquinolinesulfonic acid (28.3 g, 135 mmol) with thionyl chloride (150 mL, 2.06 mol) at room temperature and under nitrogen protection. The reaction mixture was heated to reflux and maintained for 2.5 hours. After completion of the reaction, it was cooled to room temperature and subsequently concentrated under reduced pressure to give a light yellow powder. The powder was suspended in anhydrous dichloromethane (200 mL), sonicated, filtered, and dried under reduced pressure at 40 °C to yield a final isoquinoline-5-sulfonyl chloride hydrochloride 29.2 g (111 mmol, 82% yield). The structure of the product was confirmed by 1H NMR (TFA-d): δ 8.48 (t, J = 7.9 Hz, 1H), 9.13-9.14 (m, 2H), 9.29 (d, J = 7.9 Hz, 1H), 9.57 (d, J = 7.0 Hz, 1H), 10.26 (s, 1H).

References

[1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2317 - 2333
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 1, p. 42 - 46
[3] Journal of Medicinal Chemistry, 1989, vol. 32, # 1, p. 46 - 50
[4] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 9, p. 5277 - 5284
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 5922 - 5933

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