2,2-Bis(hydroxymethyl)butyric acid
[CAS# 10097-02-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 2,2-Bis(hydroxymethyl)butyric acid
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.16
• CAS Registry Number: 10097-02-6
• EC Number: 424-090-1
• SMILES: CCC(CO)(CO)C(=O)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 109-112 °C (Expl.)
• Index of Refraction: 1.499, Calc.^*
• Boiling Point: 360.0±32.0 °C (760 mmHg), Calc.^*
• Flash Point: 185.7±21.6 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H318-H412
• Safety Statements: P264+P265-P273-P280-P305+P354+P338-P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute hazardous to the aquatic environment	Aquatic Acute	3	H402

Discovery and Applications

2,2-Bis(hydroxymethyl)butyric acid is a chemical compound primarily used in organic synthesis and as a precursor in the preparation of various derivatives, including chelating agents. The compound is characterized by two hydroxymethyl groups attached to a butyric acid backbone, which plays a significant role in its reactivity and its ability to form stable complexes with metal ions.

The discovery of 2,2-Bis(hydroxymethyl)butyric acid is part of a broader effort in the 20th century to develop chemicals with multifunctional properties, especially those that could serve as intermediates in the synthesis of more complex molecules. The compound was first synthesized and characterized in the context of developing chelating agents, which are important in fields like catalysis, environmental chemistry, and medicine. The presence of two hydroxymethyl groups provides the compound with a high potential for binding metal ions, making it a useful building block in the creation of chelating ligands.

In terms of applications, 2,2-Bis(hydroxymethyl)butyric acid has found use as a precursor for the synthesis of various chelating agents, including those that bind transition metals in biological and industrial processes. These chelating agents are particularly valuable in the treatment of metal poisoning and in analytical chemistry, where metal ion complexes are used for detecting and quantifying metals in different samples. The compound's ability to form stable, water-soluble complexes with metals such as iron, copper, and zinc makes it useful in both industrial and medicinal chemistry.

Additionally, 2,2-Bis(hydroxymethyl)butyric acid is employed in the production of polymers and resins, where it serves as a building block to create crosslinked structures. It can also be used in the synthesis of certain surfactants and as an intermediate in the preparation of other specialty chemicals.

In summary, 2,2-Bis(hydroxymethyl)butyric acid is a versatile chemical compound that serves as an important intermediate in the synthesis of chelating agents and other industrial chemicals. Its discovery was a step forward in the development of functional organic compounds with multiple uses in chemistry and industry.

References

2020. Effect of different carboxylic acid group contents on microstructure and properties of waterborne polyurethane dispersions. Journal of Polymer Research, 27(6).
DOI: 10.1007/s10965-020-02125-1

2023. Recent Advances in Polyurethane Coatings and Adhesives Derived from Vegetable Oil-Based Polyols. Journal of Polymers and the Environment, 31(10).
DOI: 10.1007/s10924-023-02920-z

2024. Contemporary Breakthroughs and Diverse Chemistry Innovations in Waterborne Polyurethane. Journal of Polymers and the Environment, 32(11).
DOI: 10.1007/s10924-024-03437-9