5-CHLORO-2-NITROBENZYL ALCOHOL Chemical Properties

Melting point:

78-79 °C (lit.)

Boiling point:

316℃

Density 

1.476

refractive index 

1.6000 (estimate)

Flash point:

145℃

storage temp. 

Sealed in dry,Room Temperature

pka

13.50±0.10(Predicted)

form 

crystalline solid

color 

off-white to faint red

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-51

Safety Statements 

24/25-36-26

WGK Germany 

3

HS Code 

29062990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-CHLORO-2-NITROBENZYL ALCOHOL Usage And Synthesis

Chemical Properties

LIGHT YELLOW TO BROWN CRYSTALLINE POWDER

Uses

5-Chloro-2-nitrobenzyl alcohol was used in the synthesis of carbamates.

Synthesis

General method: 2-nitro-5-chlorobenzaldehyde (1 eq.) was dissolved in ethanol (0.44 M) and cooled in an ice bath. To this cooled solution, sodium borohydride (1.5 eq.) was added in batches under stirring. The reaction mixture was kept stirred at 0 °C for 2 h. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solvent was removed by careful evaporation to give a semi-solid product. Subsequently, the reaction was quenched by slow addition of saturated aqueous ammonium chloride solution until the hydrogen release was complete. The aqueous phase was extracted four times with dichloromethane (CH2Cl2) and the organic phase was combined. The organic phase was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. Finally, the solvent was removed by concentration under reduced pressure to give the crude product 5-chloro-2-nitrobenzenemethanol (12), which can be used in subsequent reactions without further purification.

References

[1] Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10573 - 10576
[2] Angew. Chem., 2017, vol. 129, # 35, p. 10709 - 10712,4
[3] Synlett, 2017, vol. 28, # 14, p. 1724 - 1728
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 16, p. 5562 - 5577
[5] Journal of the American Chemical Society, 1952, vol. 74, p. 536

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