5-bromo-2-nitrobenzenamine

5-bromo-2-nitrobenzenamine Property

Melting point:

151-152 °C

Boiling point:

331.9±22.0 °C(Predicted)

Density 

1.812±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

-1.53±0.25(Predicted)

color 

Light yellow to yellow

InChI

InChI=1S/C6H5BrN2O2/c7-4-1-2-6(9(10)11)5(8)3-4/h1-3H,8H2

InChIKey

RMIFLIVHJLREFJ-UHFFFAOYSA-N

SMILES

C1(N)=CC(Br)=CC=C1[N+]([O-])=O

Safety

HS Code 

2921420090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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.

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

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

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

P405Store locked up.

P501Dispose of contents/container to..…

5-bromo-2-nitrobenzenamine Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-nitro-5-bromoaniline from 1-bromo-4-nitrobenzene: Step 1: Synthesis of 5-bromo-2-nitroaniline (142) [0745] To a solution of ethylene glycol dimethyl ether (170 mL) containing potassium tert-butoxide (21.92 g, 195 mmol) and copper(I) chloride (2.36 g, 23.8 mmol) was added dropwise a solution of 1-bromo-4-nitrobenzene (141, 8.69 g, 43.0 mmol) in DMF (45 mL) at 0 °C and protected by nitrogen, the time of dropwise addition was 50 min. After the dropwise addition, the cooling bath was removed and the reaction mixture was continued to be stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was diluted with dichloromethane, washed sequentially with aqueous ammonium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated to give the target compound 142 (7.85 g, 84% yield). [0746] 1H NMR (CDCl3) δ (ppm): 7.98 (d, J = 9.2 Hz, 1H), 7.02 (d, J = 2.0 Hz, 1H), 6.82 (dd, J = 9.2, 2.0 Hz, 1H), 6.12 (bs, 2H).

References

[1] Patent: WO2007/118137, 2007, A1. Location in patent: Page/Page column 109-110
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1437 - 1444
[3] Patent: WO2016/89830, 2016, A1. Location in patent: Page/Page column 43
[4] Patent: WO2016/89797, 2016, A1. Location in patent: Page/Page column 65
[5] Patent: WO2016/89833, 2016, A1. Location in patent: Page/Page column 42