3-Bromo-4-nitrophenol

3-Bromo-4-nitrophenol Property

Melting point:

125-1270C

Boiling point:

306.7±27.0 °C(Predicted)

Density 

1.881±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Solid

pka

6.32±0.10(Predicted)

color 

Yellow to Brown

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H410Very toxic to aquatic life with long lasting effects

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.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

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

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

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

3-Bromo-4-nitrophenol Chemical Properties,Usage,Production

Chemical Properties

Brown Solid

Synthesis

Example 1 Synthesis of 3-bromo-4-nitrophenol (Compound 4): concentrated sulfuric acid (98%, 10.0 mL, 187.4 mmol) was slowly added dropwise to a solution of NaNO3 (13.5 g, 159.6 mmol) in water (30 mL), and the reaction temperature was maintained at 0-5°C. Subsequently, a solution of 3-bromophenol (12.0 g, 69.4 mmol) dissolved in ethanol (25 mL). The reaction mixture was stirred overnight at room temperature before being poured into ice water (300 mL) and extracted with dichloromethane (3 × 100 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated, and purified by silica gel column chromatography (eluent: hexane solution of 30% ethyl acetate) to afford the target product, compound 4, in 37.1% yield (5.59 g) as a yellow solid. The structure of the product was confirmed by 1H-NMR (DMSO-d6, 400 MHz), 13C-NMR (CDCl3, 100 MHz) and mass spectrometry (ESI).

References

[1] Organic Letters, 2013, vol. 15, # 13, p. 3234 - 3237
[2] Patent: US2014/256817, 2014, A1. Location in patent: Page/Page column
[3] Patent: WO2007/30366, 2007, A1. Location in patent: Page/Page column 91-92
[4] Journal of Organic Chemistry, 2009, vol. 74, # 1, p. 212 - 221
[5] Journal of the Chemical Society, 1926, p. 159