5-HYDROXY-2-NITROBENZYL ALCOHOL

5-HYDROXY-2-NITROBENZYL ALCOHOL Property

Melting point:

111-115 °C (lit.)

Boiling point:

398.6±32.0 °C(Predicted)

Density 

1.489±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

6.99±0.10(Predicted)

Appearance

Light brown to gray Solid

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

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-HYDROXY-2-NITROBENZYL ALCOHOL Chemical Properties,Usage,Production

Uses

5-Hydroxy-2-nitrobenzyl alcohol may be used in the synthesis of 5-(2′-(dimethylamino)ethoxy)-2-nitrobenzyl alcohol. It may be used as difunctional photo-responsive initiator in the synthesis of thermo-responsive and photo-cleavable amphiphilic block copolymers containing photodegradable linkers as junction points between hydrophilic and hydrophobic chains.

Synthesis

General procedure for the synthesis of 5-hydroxy-2-nitrobenzaldehyde from 5-hydroxy-2-nitrobenzenemethanol: Sodium borohydride (1.4 g, 37.84 mmol) was slowly added to a solution of 5-hydroxy-2-nitrobenzaldehyde (4.07 g, 24.35 mmol) in methanol (30 mL) while the reaction mixture was cooled in an ice water bath. After the addition was completed, the reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was recrystallized in methanol to give 4.0 g (23.62 mmol, 97% yield) of 5-hydroxy-2-nitrobenzyl alcohol.

References

[1] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2753 - 2757
[2] Patent: US2007/213278, 2007, A1. Location in patent: Page/Page column 29; Sheet 9
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 20, p. 4309 - 4316
[4] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2434 - 2441
[5] Chemistry - A European Journal, 2015, vol. 21, # 5, p. 1873 - 1877