5-Hydroxy-2-nitrobenzaldehyde Chemical Properties

Melting point:

165-169 °C (lit.)

Boiling point:

373.0±32.0 °C(Predicted)

Density 

1.500±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

pka

6.34±0.10(Predicted)

form 

Solid

color 

Pale Yellow to Yellow

Sensitive 

Air Sensitive

BRN 

1910196

Stability:

Air Sensitive

CAS DataBase Reference

42454-06-8(CAS DataBase Reference)

NIST Chemistry Reference

5-Hydroxy-2-nitro-benzaldehyde(42454-06-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

CU6700000

HS Code 

29130000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Hydroxy-2-nitrobenzaldehyde Usage And Synthesis

Chemical Properties

Yellow powder

Uses

5-Hydroxy-2-nitrobenzaldehyde is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 409, 1979 DOI: 10.1021/jo01317a021

Synthesis

The general procedure for the synthesis of 5-hydroxy-2-nitrobenzaldehyde (formula VI) using m-hydroxybenzaldehyde (formula V, R5=H) as starting material was as follows: 3 g of m-hydroxybenzaldehyde was slowly added to 30 ml of nitric acid (density = 1.17, 28% solution), and the temperature of the solution was maintained at a temperature between 35°C and 45°C during the reaction. After the addition was completed, hydrolysis was carried out and the reaction mixture was subsequently left to stand at room temperature. The reaction produced a yellow precipitate which was filtered and the precipitate was refluxed in 20 ml of benzene for 15 to 20 minutes. The insoluble material was separated and purified by recrystallization in water. 5-Hydroxy-2-nitrobenzaldehyde (formula VI) was finally obtained in 25% yield with a melting point of 167°C (molecular formula: C7H5NO4, molecular weight = 167).

References

[1] Helvetica Chimica Acta, 1992, vol. 75, # 4, p. 1185 - 1197
[2] Patent: US5139707, 1992, A
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 3, p. 444 - 452
[4] Journal of the Chemical Society, 1925, vol. 127, p. 2171
[5] Journal of the Chemical Society, 1925, vol. 127, p. 876,877

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