5-BROMO-2-METHYL-2H-INDAZOLE Chemical Properties

Boiling point:

322.7±15.0 °C(Predicted)

Density 

1.60±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-0.06±0.30(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C8H7BrN2/c1-11-5-6-4-7(9)2-3-8(6)10-11/h2-5H,1H3

InChIKey

QFZOHVHNTZTZMJ-UHFFFAOYSA-N

SMILES

N1=C2C(C=C(Br)C=C2)=CN1C

Safety Information

HS Code 

2933998090

5-BROMO-2-METHYL-2H-INDAZOLE Usage And Synthesis

Synthesis

To a solution of 5-bromo-1H-indazole (0.19 g, 0.94 mmol) in THF (3 mL), NaH (0.04 g, 1.03 mmol) was slowly added at 0 °C. The reaction mixture was stirred at this temperature for 1 h, followed by the addition of iodomethane (0.09 mL, 1.41 mmol) at 0 °C. The reaction mixture was allowed to warm slowly to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction was quenched with water and concentrated under reduced pressure. The residue was diluted with water and extracted twice with dichloromethane (DCM). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated. Purification of the crude product by fast column chromatography (eluent: hexane/ethyl acetate = 10:1) afforded 5-bromo-1-methyl-1H-indazole (ii) (88.7 mg, 42.5%) and 5-bromo-2-methyl-2H-indazole (iii) (60.9 mg, 29%), both as white solids. The 1H-NMR (400 MHz, DMSO-d6) δ ppm of compound ii: 8.02 (d, 1H), 7.99 (d, 1H), 7.64 (d, 1H), 7.50 (dd, 1H), 4.04 (s, 3H). lcms (Method A): [MH]+ = 211/213, tR = 5.19 min. compound iii The 1H-NMR (400 MHz, DMSO-d6) δ ppm: 8.33 (s, 1H), 7.95 (d, 1H), 7.57 (d, 1H), 7.30 (dd, 1H), 4.16 (s, 3H). lCMS (Method A): [MH]+ = 211/213, tR = 4.95 min.

References

[1] Patent: CN105254613, 2016, A. Location in patent: Paragraph 0131; 0132; 0133; 0134; 0135
[2] Journal of Organic Chemistry, 2018, vol. 83, # 12, p. 6334 - 6353
[3] Patent: WO2011/18454, 2011, A1. Location in patent: Page/Page column 60-61
[4] Patent: WO2011/20861, 2011, A1. Location in patent: Page/Page column 59
[5] Chemische Berichte, 1922, vol. 55, p. 1141,1157

5-BROMO-2-METHYL-2H-INDAZOLE(465529-56-0)Related Product Information

• 5-Bromo-2-methyl-2H-pyrazolo[3,4-c]pyridine
• 5-Bromo-2-methyl-2H-indazole-3-carbaldehyde
• 6-BROMO-1-METHYL-1H-INDAZOLE
• 5-BROMO-1-METHYL-1H-INDAZOLE
• 5-BROMO-2-METHYL-2H-INDAZOLE