| Identification | Back Directory | [Name]
Isoquinoline-4-carbaldehyde | [CAS]
22960-16-3 | [Synonyms]
RARECHEM AK ML 0134
4-Formylisoquinoline
4-Isoquinolinecarbaldehyde
ISOQUINOLINE-4-CARBALDEHYDE
4-ISOQUINOLINECARBOXALDEHYDE
Isoquinoline-4-carboxaldehyde
Isoquinoline-4-carbaldehyde ,98%
4-Isoquinolinecarboxaldehyde 97%
4-Isoquinolinecarboxaldehyde (7CI,8CI,9CI)
Isoquinoline-4-carbaldehyde ISO 9001：2015 REACH | [Molecular Formula]
C10H7NO | [MDL Number]
MFCD00829440 | [MOL File]
22960-16-3.mol | [Molecular Weight]
157.17 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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