5-BROMO-1-METHYL-1H-INDAZOLE

5-BROMO-1-METHYL-1H-INDAZOLE Property

Melting point:

111-112 °C(Solv: ligroine (8032-32-4))

Boiling point:

293.6±13.0 °C(Predicted)

Density 

1.60±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

0.36±0.30(Predicted)

color 

Orange

InChI

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

InChIKey

RMCHMXPTUMFFBZ-UHFFFAOYSA-N

SMILES

N1(C)C2=C(C=C(Br)C=C2)C=N1

Safety

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

5-BROMO-1-METHYL-1H-INDAZOLE Chemical Properties,Usage,Production

Uses

5-?Bromo-?1-?methyl-1H-?indazole is an antibacterial drugs with inhibitory activity against multidrug-resistant (MDR) pathogens.

Synthesis

5-Bromoindazole (590 mg, 2.99 mmol) was dissolved in tetrahydrofuran (10 mL) and stirred under ice bath conditions and sodium hydride (180 mg, 80% dispersed in mineral oil, 6.00 mmol) was added slowly. After stirring for 30 minutes, iodomethane (468 mg, 3.30 mmol) was added and stirring was continued for 3 hours. After completion of the reaction, the reaction mixture was warmed to room temperature and the reaction was quenched by the addition of water (20 mL). The reaction was extracted with ethyl acetate (20 mL × 3), and the organic phases were combined and washed with saturated saline (50 mL × 3). The organic phase was dried with anhydrous sodium sulfate, filtered and the solvent was removed by rotary evaporation. The residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate = 10:1 to 3:1) to afford 5-bromo-2-methyl-2H-indazole (A14-2, 230 mg, 36%) and 1-methyl-5-bromo-1H-indazole (A14-3, 330 mg, 52%).A14-2 was an off-white solid, 1H NMR (400 MHz, DMSO ) δ 8.33 (s, 1H), 7.96-7.95 (m, 1H), 7.57 (d, J = 9.2 Hz, 1H), 7.31-7.28 (m, 1H), 4.16 (s, 3H).A14-3 is a white solid.

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