Malonic acid
[CAS# 141-82-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Acyclic carboxylic acid
• Name: Malonic acid
• Synonyms: 1,3-Propanedioic acid
• Molecular Formula: C₃H₄O₄
• Molecular Weight: 104.06
• CAS Registry Number: 141-82-2
• EC Number: 205-503-0
• SMILES: C(C(=O)O)C(=O)O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*, 1.631 g/mL (15 °C)
• Melting Point: 134 °C
• Index of Refraction: 1.479, Calc.^*
• Boiling Point: 386.8±25.0 °C (760 mmHg), Calc.^*, 140 °C (760 mmHg)
• Flash Point: 201.9±19.7 °C, Calc.^*, 157 °C

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H315-H318-H319
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H336
Skin corrosion	Skin Corr.	1	H314

Discovery and Applications

Malonic acid, a dicarboxylic acid with the chemical formula C3H4O4, has played a significant role in organic chemistry since its discovery in the 19th century. It was first identified in the early 1800s by the French chemist Pierre Robiquet, who isolated it from the bitter almond oil, where it occurs naturally as part of various plant metabolic processes. The name "malonic" is derived from the Latin word "malon," meaning "apple," reflecting its presence in fruit.

The structure of malonic acid features two carboxylic acid groups (-COOH) attached to a three-carbon backbone, making it a simple yet versatile compound. Its discovery paved the way for its use in various synthetic applications, particularly in the production of other organic compounds.

One of the primary applications of malonic acid is as a key intermediate in organic synthesis. It is widely used in the malonic ester synthesis, where it reacts with various alkyl halides to form malonic esters. These esters serve as important building blocks in the preparation of α-substituted carboxylic acids, which are significant in pharmaceuticals and agrochemicals. The ability to introduce functional groups at the α-position of carboxylic acids through malonic acid derivatives makes it a valuable reagent in synthetic organic chemistry.

Malonic acid also finds applications in the manufacture of polymers and resins. It can be polymerized to produce polyesters and polyamides, contributing to the production of various plastic materials with diverse applications, including coatings, adhesives, and fibers. Its role as a precursor in the synthesis of biodegradable polymers has gained attention in recent years, as environmental concerns drive the search for sustainable materials.

Additionally, malonic acid has been explored for its potential health benefits and applications in the pharmaceutical industry. It is a precursor for the synthesis of certain pharmaceuticals, including some anti-inflammatory and analgesic agents. Its ability to participate in biochemical reactions has led researchers to investigate its role in cellular metabolism and energy production.

In the field of agriculture, malonic acid has been utilized as a herbicide and fungicide. Its derivatives are being studied for their efficacy in controlling plant diseases and pests, providing an alternative to conventional agrochemicals.

While malonic acid is generally regarded as safe, it is important to handle it with care, as exposure can lead to irritation of the skin and mucous membranes. Appropriate safety precautions should be taken when working with this compound in laboratory and industrial settings.

In summary, malonic acid is a vital compound in organic chemistry, known for its versatile applications in synthesis, polymer production, and pharmaceuticals. Its historical significance and continued relevance underscore its importance in both academic research and industrial processes, making it a key player in the development of new materials and pharmaceuticals.

References

2003. Cantharidin analogues: synthesis and evaluation of growth inhibition in a panel of selected tumour cell lines. Bioorganic Chemistry, 31(1).
DOI: 10.1016/s0045-2068(02)00524-2

2003. Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles. Accounts of Chemical Research, 36(4).
DOI: 10.1021/ar0201106

1984. Fluorometric determination of malonic acid with dicyclohexylcarbodiimide. Analytical Biochemistry, 140(1).
DOI: 10.1016/0003-2697(84)90153-2