Isoquinoline-4-carbaldehyde Chemical Properties

Melting point:

101-106℃

Boiling point:

331.7±15.0 °C(Predicted)

Density 

1.223±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

3.49±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C10H7NO/c12-7-9-6-11-5-8-3-1-2-4-10(8)9/h1-7H

InChIKey

RNQQJLYJLDQGGL-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-36/37/38-20/21/22

Safety Statements 

26-36/37/39-22

RIDADR 

2811

WGK Germany 

3

HS Code 

29339900

Isoquinoline-4-carbaldehyde Usage And Synthesis

Chemical Properties

Off-white to yellow or brown solid

Synthesis

Under nitrogen protection, 4-bromoisoquinoline (2.0 g, 9.6 mmol) was dissolved in 30 mL of redistilled tetrahydrofuran (THF) and cooled to -65°C. n-Butyllithium (4.0 mL, 10 mmol, 2.5 M solution in THF) was added slowly and dropwise. Maintaining this temperature, the reaction mixture was stirred for 30 min. Subsequently, N,N-dimethylformamide (730 mg, 10 mmol) was added dropwise and stirring was continued for 1 h at the same temperature. After completion of the reaction, 100 mL of saturated aqueous ammonium chloride solution was added to the mixture. The reaction mixture was extracted with ethyl acetate (50 mL × 3). The organic layers were combined, washed with 100 mL of brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (elution gradient: 0-100% ethyl acetate/petroleum ether) to give isoquinoline-4-carboxaldehyde (550 mg, yellow solid, yield: 36%).1H NMR (400 MHz, CDCl3): δ 10.41 (s, 1H), 9.45 (s, 1H), 9.22 (d, J = 8.4 Hz, 1H) 8.96 (s, 1H), 8.10 (d, J = 8.4 Hz, 1H), 7.96-7.92 (m, 1H), 7.76 (t, J = 8.4 Hz, 1H).

References

[1] Tetrahedron, 1998, vol. 54, # 35, p. 10317 - 10328
[2] European Journal of Organic Chemistry, 2009, # 26, p. 4458 - 4467
[3] Patent: US2017/37050, 2017, A1. Location in patent: Paragraph 0346-0349

Isoquinoline-4-carbaldehyde(22960-16-3)Related Product Information

• Isoquinoline
• 2-Quinolinecarboxaldehyde
• Paraformaldehyde
• ISOQUINOLINE-1-CARBALDEHYDE
• ISOQUINOLINE-5-CARBALDEHYDE
• Isoquinoline-3-carbaldehyde
• ISOQUINOLINE-3-CARBOXYLIC ACID
• 6-Isoquinolinecarboxaldehyde (9CI)
• 6-Isoquinolinyl-boronic acid
• Isoquinoline-3-carboxylic acid
• 8-isoquinolinyl-boronic acid
• C-ISOQUINOLIN-4-YL-METHYLAMINE
• ISOQUINOLINE-5-CARBOXYLIC ACID
• 7-Isoquinolinecarboxaldehyde (6CI,9CI)
• Isoquinoline-5-sulphonyl chloride hydrochloride
• ISOQUINOLINE N-OXIDE
• METHYL 4-ISOQUINOLINECARBOXYLATE
• ISOQUINOLINE-4-BORONIC ACID HYDROCHLORIDE