Isoquinoline-3-carboxylic acid Chemical Properties

Melting point:

166-167°C

Boiling point:

366.4±17.0 °C(Predicted)

Density 

1.339±0.06 g/cm3(Predicted)

storage temp. 

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-37/39

HS Code 

2933499090

Isoquinoline-3-carboxylic acid Usage And Synthesis

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

Isoquinoline-3-carboxylic acid(6624-49-3)Related Product Information

• 6-isoquinolinecarboxylic acid
• 7-isoquinolinecarboxylic acid
• 3-Isoquinolinol(9CI)
• 6-AMINOISOQUINOLINE
• C-ISOQUINOLIN-4-YL-METHYLAMINE
• 6-Isoquinolinyl-boronic acid
• Isoquinoline-4-carbaldehyde
• 6-Isoquinolinecarboxaldehyde (9CI)
• ISOQUINOLINE-3-CARBOXYLIC ACID
• 8-isoquinolinyl-boronic acid
• Isoquinoline
• ISOQUINOLINE-1-CARBOXYLIC ACID
• ISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER
• ISOQUINOLINE-5-CARBOXYLIC ACID
• 7-Isoquinolinecarboxaldehyde (6CI,9CI)
• ISOQUINOLINE-5-CARBALDEHYDE
• Isoquinolin-3-ylMethanaMine hydrochloride
• ISOQUINOLINE-1-CARBALDEHYDE