meso-2,3-Dibromosuccinic acid
[CAS# 608-36-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty acid
• Name: meso-2,3-Dibromosuccinic acid
• Synonyms: (2S,3R)-2,3-dibromobutanedioic acid
• Molecular Formula: C₄H₄Br₂O₄
• Molecular Weight: 275.88
• CAS Registry Number: 608-36-6
• EC Number: 452-290-7
• SMILES: [C@@H]([C@@H](C(=O)O)Br)(C(=O)O)Br

Properties

• Water solubility: 20 g/L (17 °C)
• Density: 2.5±0.1 g/cm³, Calc.^*
• Melting point: 288-290 °C
• Index of Refraction: 1.622, Calc.^*
• Boiling Point: 262.4±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 112.5±27.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H290-H314-H318
• Safety Statements: P234-P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P321-P337+P317-P363-P390-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1C	H314
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 3261

Discovery and Applications

meso-2,3-Dibromosuccinic acid is a halogenated derivative of succinic acid, featuring two bromine atoms attached to the second and third carbon atoms of the succinic acid backbone. Its chemical formula is C4H4Br2O4, and it is recognized for its distinct stereochemistry, which classifies it as a meso compound. The discovery of meso-2,3-dibromosuccinic acid dates back to the mid-20th century, with its synthesis first reported in the context of studies exploring the reactivity of succinic acid derivatives.

The synthesis of meso-2,3-dibromosuccinic acid can be achieved through the bromination of succinic acid or its esters, which involves the substitution of hydrogen atoms with bromine. This reaction not only yields the dibromosuccinic acid but also provides insight into the chemical behavior of dibromo compounds, particularly regarding their reactivity and stereochemistry. The unique properties of meso-2,3-dibromosuccinic acid have led to its investigation in various fields of research.

One of the prominent applications of meso-2,3-dibromosuccinic acid is in organic synthesis as a versatile intermediate. Its structure allows it to undergo a variety of chemical transformations, including esterification and amidation, facilitating the production of complex molecules. These transformations make it a valuable building block for the synthesis of pharmaceuticals and agrochemicals. Researchers have utilized meso-2,3-dibromosuccinic acid in the development of various bioactive compounds, demonstrating its potential in medicinal chemistry.

Furthermore, meso-2,3-dibromosuccinic acid has garnered interest in the study of biochemical pathways, particularly in the context of metabolic studies. It has been shown to act as a competitive inhibitor of certain enzymes involved in the citric acid cycle, such as succinate dehydrogenase. This inhibition can influence metabolic processes, making meso-2,3-dibromosuccinic acid a useful tool for probing metabolic pathways and understanding enzyme kinetics. By studying its effects on cellular metabolism, researchers can gain insights into metabolic diseases and identify potential therapeutic targets.

In addition to its applications in organic synthesis and biochemistry, meso-2,3-dibromosuccinic acid has been explored in materials science. Its ability to participate in polymerization reactions allows for the incorporation of brominated structures into polymers, potentially enhancing their properties. This feature is particularly useful in developing materials with improved thermal stability, flame retardancy, and mechanical strength.

Despite its various applications, the use of meso-2,3-dibromosuccinic acid must be approached with caution due to its potential toxicity. As a brominated compound, it may pose health risks, necessitating proper handling and safety measures in laboratory and industrial settings. Research continues to investigate its safety profile and establish guidelines for its use in various applications.

In summary, meso-2,3-dibromosuccinic acid is a significant compound with a notable history of discovery and diverse applications in organic synthesis, biochemistry, and materials science. Its unique properties and role as a metabolic inhibitor continue to make it a subject of interest in scientific research, highlighting its relevance across multiple disciplines.

References

2011. (mu-2,3-Dibromosuccinato-kappa2O1:O4)bis[methanolato-kappaO)triphenylantimony(V)]. Acta Crystallographica. Section E, Structure Reports Online, 67(6).
DOI: 10.1107/s1600536811016114

2005. (RS)-2,3-Dibromosuccinic acid. Acta Crystallographica Section E Structure Reports Online, 62(1).
DOI: 10.1107/s1600536805040493

2006. CCDC 296661: Experimental Crystal Structure Determination.
DOI: 10.5517/cc9ypqm