5'-BROMO-2'-HYDROXY-3'-NITROACETOPHENONE

5'-BROMO-2'-HYDROXY-3'-NITROACETOPHENONE Property

Melting point:

129-132 °C(lit.)

Boiling point:

272.9℃

Density 

1.763

Flash point:

118.9℃

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

6.47±0.38(Predicted)

color 

Light yellow to Yellow to Orange

CAS DataBase Reference

70978-54-0(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29145090

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.

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

5'-BROMO-2'-HYDROXY-3'-NITROACETOPHENONE Chemical Properties,Usage,Production

Uses

5'-Bromo-2'-hydroxy-3'-nitroacetophenone is used as a chemical reagent in the synthesis of amides and benzoxazoles directly using a sulfate catalyst and microwaves. 1-(5-Bromo-2-hydroxy-3-nitrophen yl)ethanone is used in studies involving HIV-1 integrase inhibitors.

Preparation

Preparation by nitration of 5-bromo-2-hydroxyacetophenone in refluxing carbon tetrachloride (88%).

Synthesis

1. Synthesis of 5-bromo-2-hydroxy-3-nitroacetophenone To a solution of 5-bromo-2-hydroxyacetophenone (23.7 g, 0.110 mol) in carbon tetrachloride (90 mL) was slowly added concentrated nitric acid (17.2 mL). The reaction mixture was stirred at 75 °C for 50 min and subsequently cooled to room temperature. The precipitated solid was collected by filtration and washed with cold carbon tetrachloride. After vacuum drying, 20.9 g of the target product 5-bromo-2-hydroxy-3-nitroacetophenone was obtained as a light yellow solid in 73% yield. 1H NMR (300 MHz, CDCl3) δ: 2.73 (s, 3H), 8.14 (d, 1H), 8.31 (d, 1H), 12.92 (s, 1H).

References

[1] Patent: US5990142, 1999, A
[2] Patent: EP1391451, 2004, A1. Location in patent: Page 113
[3] Patent: WO2017/221002, 2017, A1. Location in patent: Page/Page column 92