1-BOC-4-BROMO-1H-INDAZOLE

1-BOC-4-BROMO-1H-INDAZOLE Property

Boiling point:

377.4±34.0 °C(Predicted)

Density 

1.46±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-2.73±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C12H13BrN2O2/c1-12(2,3)17-11(16)15-10-6-4-5-9(13)8(10)7-14-15/h4-7H,1-3H3

InChIKey

OFVPGIHEBLOESV-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)C2=C(C(Br)=CC=C2)C=N1

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

1-BOC-4-BROMO-1H-INDAZOLE Chemical Properties,Usage,Production

Synthesis

At room temperature, 4-bromo-1H-indazole (1.0 g, 5.07 mmol) was dissolved in dichloromethane (DCM, 20 mL), followed by sequential addition of triethylamine (TEA, 0.85 mL, 6.1 mmol) and 4-dimethylaminopyridine (DMAP, 0.062 g, 0.50 mmol). Di-tert-butyl dicarbonate (Boc anhydride, 1.28 mL, 5.58 mmol) was added slowly and dropwise to the reaction mixture under continuous stirring. The reaction mixture was continued to be stirred at room temperature for 2.5 hours. Upon completion of the reaction, the mixture was poured into water (30 mL) and extracted with dichloromethane (2 x 30 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography (eluent: hexane solution of 15-20% ethyl acetate) to afford the target compound tert-butyl 4-bromo-1H-indazole-1-carboxylate (1.5 g, 5.06 mmol). The product was analyzed by LCMS (Method C) showing a retention time of 2.601 min and a mass spectrum (MS: ES+) m/z of 297.19; NMR hydrogen spectrum (400 MHz, DMSO-d6) δ ppm: 8.20 (s, 1H), 8.15 (d, J = 8.0 Hz, 1H), 7.47 (dd, J = 0.8 Hz, 7.6 Hz. 1H), 7.37-7.41 (m, 1H), 1.74 (s, 9H).

References

[1] Patent: WO2007/21937, 2007, A2. Location in patent: Page/Page column 42
[2] Patent: WO2017/109488, 2017, A1. Location in patent: Page/Page column 43