| Identification | More | [Name]
Isoquinoline-3-carboxylic acid | [CAS]
6624-49-3 | [Synonyms]
AKOS BB-8838
ISOQUINOLINE-3-CARBOXYLIC ACID
RARECHEM AL BO 1320
3-Isoquinolinecarboxylic acid
3-ISOQUINALDIC ACID
3-ISOQUINOLINECARBOXYLIC ACID 98% | [Molecular Formula]
C10H7NO2 | [MDL Number]
MFCD00075137 | [Molecular Weight]
173.17 | [MOL File]
6624-49-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
166-167°C | [Boiling point ]
366.4±17.0 °C(Predicted) | [density ]
1.339±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMF: 20 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 20 mg/ml; Ethanol: 5 mg/ml | [form ]
A crystalline solid | [pka]
1.20±0.30(Predicted) | [color ]
Off-white to light yellow | [InChI]
InChI=1S/C10H7NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-6H,(H,12,13) | [InChIKey]
KVMMIDQDXZOPAB-UHFFFAOYSA-N | [SMILES]
C1C2=C(C=CC=C2)C=C(C(O)=O)N=1 | [CAS DataBase Reference]
6624-49-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [HS Code ]
2933499090 |
| Hazard Information | Back Directory | [Uses]
Isoquinoline-3-carboxylic Acid is a reagent used in the synthesis of an anti-Trypanosoma agent, which acts as a minor groove binder affecting the biological activity. | [Synthesis]
At 0°C, 10.0 g (0.046 mmol) of (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was dissolved in 200 ml of N,N-dimethylformamide and 5.0 g (0.032 mmol) of potassium permanganate (KMnO4) was slowly added over 30 min. The reaction mixture was stirred at room temperature for 100 h. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio CCl3:CH3OH = 5:1) to confirm complete consumption of (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. Subsequently, the reaction mixture was concentrated under vacuum. The residue was washed several times with distilled water to give 8.1 g (83% yield) of isoquinoline-3-carboxylic acid as a yellow powder. The product was analyzed by ESI-MS (m/e) showing [M + H]+ peak of 174; 1H NMR (300 MHz, DMSO) δ/ppm = 10.81 (s, 1H), 9.52 (s, 1H), 8.43 (s, 1H), 7.52 (m, 4H); 13C NMR (75 MHz, DMSO) δ/ppm = 164.9, 152.3, 143.5, 136.2, 131.3, 129.7, 127.2, 125.8. | [References]
[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 5, p. 1672 - 1681
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4434 - 4436
[3] Patent: CN106986825, 2017, A
[4] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 34, p. 8957 - 8965 |
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