8-Bromoisoquinoline Chemical Properties

Melting point:

80,5 C

Boiling point:

312.3±15.0 °C(Predicted)

Density 

1.564±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH 7.2) (1:8): .5 mg/ml

form 

powder to crystal

pka

4.63±0.23(Predicted)

color 

Light orange to Yellow to Green

InChI

InChI=1S/C9H6BrN/c10-9-3-1-2-7-4-5-11-6-8(7)9/h1-6H

InChIKey

DPRIHFQFWWCIGY-UHFFFAOYSA-N

SMILES

C1C2=C(C=CC=C2Br)C=CN=1

CAS DataBase Reference

63927-22-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn,T

Risk Statements 

36/37/38-20/21/22-25

Safety Statements 

26-36-45

RIDADR 

2811

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29334900

8-Bromoisoquinoline Usage And Synthesis

Chemical Properties

Yellow powder

Uses

8-Bromoisoquinoline is an intermediate used to prepare 4-?((2-?Hydroxy-?3-?methoxybenzyl)?amino)?benzenesulfonamide derivatives as potent and selective inhibitors of 12-?Lipoxygenase. It is also used in the synthesis of selective excitatory amino acid transporter subtype 1 (EAAT1) Inhibitor UCPH-?102.

Synthesis

1. 2-Bromobenzaldehyde (50 g, 270 mmol), aminoglyoxal dimethyl acetal (28.4 g, 270 mmol) and toluene (400 mL) were mixed under argon protection and heated to reflux. The dehydration reaction was carried out for 2.0 hours using a Dean-Stark apparatus. After dehydration was completed, reflux was continued for 1.0 hour. 2. Upon completion of the reaction, toluene was removed by evaporation under reduced pressure, the residue was dissolved in dichloromethane (600 mL), and the solution was cooled to 0°C. The reaction was then purged by evaporation under reduced pressure. 3. Aluminum chloride (118.9 g, 891.7 mmol) was slowly added to the cooled solution under argon protection, and the reaction mixture was then stirred at 45°C for 2.0 hours. 4. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water. 5. The dichloromethane layer was separated by alkalizing the mixture with 10% sodium hydroxide solution. The aqueous layer was re-extracted with dichloromethane (2 x 100mL). 6. The methylene chloride layer was combined, washed with brine and dried over anhydrous sodium sulfate. 7. The dichloromethane was removed by evaporation and the residue was purified by column chromatography on silica gel (100-200 mesh) to afford 8-bromoisoquinoline as an off-white solid (28 g, 49.8% yield) using a 5-8% ethyl acetate solution in hexane as the mobile phase. MS (ESI) m/z: 208 [M(79Br)+1], 210 [M(81Br)+1]; 1H NMR (400 MHz, DMSO-d6): δ 7.17 (t, J=7.8 Hz, 1H); 7.91 (d, J=6.0 Hz, 1H); 8.02 (d, J=8.4 Hz, 1H); 8.05 (d, J= 8.8 Hz, 1H); 8.65 (d, J=5.2 Hz, 1H); 9.48 (s, 1H).

References

[1] Patent: WO2016/21742, 2016, A1. Location in patent: Paragraph 0222; 0223

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