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2,5-diiodobenzoic acid

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Identification
Molecular formula
C7H4I2O2
CAS number
610-92-4
IUPAC name
2,5-diiodobenzoic acid
State
State

At room temperature, 2,5-diiodobenzoic acid is in a solid state, existing as a crystalline powder.

Melting point (Celsius)
222.00
Melting point (Kelvin)
495.15
Boiling point (Celsius)
289.80
Boiling point (Kelvin)
562.95
General information
Molecular weight
389.89g/mol
Molar mass
389.8940g/mol
Density
2.4880g/cm3
Appearence

2,5-Diiodobenzoic acid appears as a white to off-white crystalline powder. It is typically odorless and forms prismatic crystals. The compound may exhibit slight yellowing upon exposure to light or air over prolonged periods.

Comment on solubility

Solubility of 2,5-diiodobenzoic acid

2,5-diiodobenzoic acid, with the chemical formula C7H4I2O2, presents intriguing solubility characteristics that can influence its applications in various fields. Here’s a comprehensive overview of its solubility:

  • Water Solubility: This compound is generally insoluble in water due to its hydrophobic iodine substituents, which hinder its interaction with water molecules.
  • Organic Solvents: However, 2,5-diiodobenzoic acid is often soluble in a range of organic solvents such as:
    • Dimethyl sulfoxide (DMSO)
    • Ethanol
    • Acetone
  • pH Influence: The solubility of this acid may also be affected by the pH of the solution. In more alkaline conditions, it can dissociate, potentially increasing its solubility.

As with many carboxylic acids, the presence of the I atoms significantly affects the polarity and, consequently, the solubility of the compound. Understanding these properties is crucial for chemists when considering applications in synthesis or formulation. Remember, "like dissolves like" - the more polar the solvent, the better it will dissolve polar or ionic substances, which is an essential principle when working with 2,5-diiodobenzoic acid.

Interesting facts

Interesting Facts about 2,5-Diiodobenzoic Acid

2,5-Diiodobenzoic acid is a fascinating compound primarily known for its substitution pattern on the benzene ring, which includes iodine atoms at the 2 and 5 positions. This unique configuration actively influences its chemical properties and reactivity.

Key Attributes:

  • Halogenated Compound: As a diiodo derivative of benzoic acid, it showcases the significant effects halogens, such as iodine, have on the aromatic system, including electron-withdrawing properties.
  • Acidity: The presence of the carboxylic acid group enhances its acidity compared to its non-iodinated counterparts, making it a valuable compound in organic synthesis.
  • Application in Synthesis: 2,5-Diiodobenzoic acid serves as a potent precursor in various synthetic pathways, particularly in the development of pharmaceuticals and agrochemicals.

Scientific Relevance:

This compound is particularly interesting due to its utility in the field of medicinal chemistry. The iodine atoms contribute to potential biological activity, making it a candidate for further investigation in drug development. Researchers often explore its interactions with biological systems to gain insights into how modifications on the aromatic ring can alter biological behavior.

Research Highlights:

  • Environmental Studies: The environmental impact of halogenated compounds is a growing concern, and 2,5-diiodobenzoic acid can be used to study degradation pathways of iodinated organic compounds.
  • Reactivity Studies: Its reactivity brings a myriad of reactions such as nucleophilic aromatic substitution, making it a valuable subject in organic reaction mechanism studies.

In summary, 2,5-diiodobenzoic acid exemplifies how minor modifications within a molecular structure can lead to significant differences in reactivity and application, providing students and scientists alike with a platform for exploration and discovery in chemistry.

Synonyms
2,5-Diiodobenzoic acid
14192-12-2
BENZOIC ACID, 2,5-DIIODO-
8GD4M9C3GV
NSC-97505
DTXSID10161858
4-09-00-01044 (Beilstein Handbook Reference)
DTXCID6084349
604-262-2
MFCD00045801
2,5-Dijodbenzoesaeure [German]
2,5-Diiodobenzoicacid
2,5-Dijodbenzoesaeure
NSC 97505
Benzoic acid,2,5-diiodo-
BRN 2090444
NSC97505
UNII-8GD4M9C3GV
SCHEMBL1277864
2,5-Diiodobenzoic acid, 97%
NSKPFWAAYDFCFS-UHFFFAOYSA-N
PAA19212
BBL035879
STK390164
AKOS000109332
CS-W009762
NCGC00341820-01
AC-30079
CS-12557
SY062550
DB-020088
NS00024607
ST50920633
EN300-66176
AB01334417-02
Z1037337344