1,3-Dichloroisoquinoline Chemical Properties

Melting point:

121-122 °C (lit.)

Boiling point:

307°C(lit.)

Density 

1.407±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

-1.49±0.50(Predicted)

color 

Light yellow to Brown to Dark green

InChI

InChI=1S/C9H5Cl2N/c10-8-5-6-3-1-2-4-7(6)9(11)12-8/h1-5H

InChIKey

BRGZEQXWZWBPJH-UHFFFAOYSA-N

SMILES

C1(Cl)C2=C(C=CC=C2)C=C(Cl)N=1

CAS DataBase Reference

7742-73-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich

1,3-Dichloroisoquinoline Usage And Synthesis

Chemical Properties

White to brown crystalline powder

Uses

1,3-Dichloroisoquinoline may be used in the facile synthesis of 1,3,4-trisubstituted isoquinoline derivatives.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 5481, 1958 DOI: 10.1021/ja01553a042

General Description

1,3-Dichloroisoquinoline undergoes Pd(PPh₃)₄ catalyzed regioselective coupling with arylboronic acids to afford to 1-aryl-3-chloroisoquinolines. Reaction of amine with 1,3-dichloroisoquinoline has been studied. Regioselectivity of the Stille coupling reaction of (1-ethoxyvinyl)tri(n-butyl)stannane with 1,3-dichloroisoquinoline has been investigated.

Synthesis

Example 60B Synthesis of 1,3-dichloroisoquinoline: The product of Example 60A, 1,3-[2H,4H]-isoquinolinedione (6.5 g, 40.4 mmol) was mixed with phenylphosphinic acid dichloride (11.5 mL, 81.1 mmol) and the reaction was heated for 3 hours at 160 °C. After the reaction was completed, it was cooled to room temperature and left to stand overnight. The reaction mixture was dissolved in tetrahydrofuran (200 mL) and hydrolyzed by adding water (60 mL), followed by concentration under reduced pressure to remove the tetrahydrofuran. The resulting aqueous phase was neutralized with concentrated NH4OH, followed by extraction with ethyl acetate. The organic phases were combined, washed sequentially with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 1,3-dichloroisoquinoline as a yellow flaky solid (6.92 g, 74% yield).

References

[1] Patent: US2005/113576, 2005, A1. Location in patent: Page/Page column 30
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3651 - 3660
[3] Patent: US6340759, 2002, B1. Location in patent: Example 17
[4] Patent: WO2010/127855, 2010, A1. Location in patent: Page/Page column 136; 137

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