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4-Hydroxy-3-nitrobenzoic acid

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Identification
Molecular formula
C7H5NO5
CAS number
619-80-7
IUPAC name
4-hydroxy-3-nitro-benzoic acid
State
State

At room temperature, 4-Hydroxy-3-nitrobenzoic acid is found in a solid state with a crystalline appearance.

Melting point (Celsius)
220.00
Melting point (Kelvin)
493.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
197.12g/mol
Molar mass
197.1360g/mol
Density
1.5787g/cm3
Appearence

4-Hydroxy-3-nitrobenzoic acid typically appears as a yellow crystalline solid.

Comment on solubility

Solubility of 4-hydroxy-3-nitro-benzoic acid

4-hydroxy-3-nitro-benzoic acid, also known as picramic acid, exhibits interesting solubility characteristics. Here are some key points:

  • Solubility in Water: This compound displays limited solubility in water, largely due to the presence of its aromatic structure which impedes the formation of hydrogen bonds with water molecules.
  • Solubility in Organic Solvents: It is more soluble in organic solvents like ethanol and acetone, which can better interact with its non-polar regions.
  • Effect of pH: The solubility can be influenced by the pH of the solution since the carboxylic acid group can ionize, potentially increasing its solubility in alkaline conditions.
  • Practical Implications: For applications requiring dissolution, it is advisable to consider the solvent used; for instance, utilizing methanol or DMSO might enhance solubility for better experimental results.

In summary, 4-hydroxy-3-nitro-benzoic acid is notably more soluble in organic media than in water, and its solubility can be modified by changing the pH of the environment. This versatility in solubility is crucial for its application in various chemical processes.

Interesting facts

Interesting Facts About 4-Hydroxy-3-nitro-benzoic Acid

4-Hydroxy-3-nitro-benzoic acid, also known as picric acid, is a fascinating compound with a rich history and diverse applications. Here are some compelling facts about this compound:

  • Historical Significance: Picric acid was first synthesized in the mid-19th century, and it quickly garnered attention for its powerful explosive capabilities. It played a significant role in World War I as an explosive for artillery shells.
  • Chemical Structure: The compound features both a nitro group and a hydroxyl group attached to a benzoic acid core. This unique structure contributes to its reactivity and versatility in various chemical reactions.
  • Indicators and Dyes: Beyond its explosive properties, 4-hydroxy-3-nitro-benzoic acid has been utilized in the synthesis of various dyes and indicators due to its vibrant color properties.
  • Biological Aspects: There is research suggesting that certain nitro compounds, including picric acid, exhibit antibacterial and antifungal activities, making them of interest in medicinal chemistry.
  • Regulatory Aspects: Due to its hazardous nature and potential for misuse, 4-hydroxy-3-nitro-benzoic acid is subject to stringent regulations in many countries.

In summary, 4-hydroxy-3-nitro-benzoic acid is not just a compound of interest due to its explosive characteristics but also due to its applications in dyes, indicators, and potential medicinal properties. As chemists continue to explore its capabilities, this compound remains a notable subject of study.

Synonyms
4-HYDROXY-3-NITROBENZOIC ACID
616-82-0
Benzoic acid, 4-hydroxy-3-nitro-
3-Nitro-4-hydroxybenzoic acid
3-Nitro-4-hydrobenzoic acid
8SL84Q8B6C
EINECS 210-494-1
NSC 78436
NSC-78436
3,4-Nitrohydroxybenzoic acid
QRYSWXFQLFLJTC-UHFFFAOYSA-
DTXSID20210609
4-hydroxy-3-nitrobenzoate
DTXCID00133100
Benzoic acid, 4-hydroxy-3-nitro-(8CI)
Benzoic acid, 4-hydroxy-3-nitro-(8CI)(9CI)
210-494-1
inchi=1/c7h5no5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9h,(h,10,11)
qryswxfqlfljtc-uhfffaoysa-n
4-hydroxy-3-nitro-benzoic acid
MFCD00007119
4-Hydroxy-3-nitrobenzoicacid
NSC78436
UNII-8SL84Q8B6C
SCHEMBL106249
CHEBI:203320
STL197510
4-Hydroxy-3-nitrobenzoic acid, 98%
AKOS003382446
CS-W017067
FH34749
AC-10247
AS-12419
DB-053964
H0910
NS00034764
EN300-53840
Z385458396