Methyl 2-hydroxyisobutyrate
[CAS# 2110-78-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: Methyl 2-hydroxyisobutyrate
• Synonyms: Methyl 2-hydroxy-2-methylpropionate; 2-Hydroxyisobutyric acid methyl ester; 2-Hydroxy-2-methylpropanoic acid methyl ester; alpha-Hydroxyisobutyric acid methyl ester; Methyl 2-methyllactate
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.13
• CAS Registry Number: 2110-78-3
• EC Number: 218-301-2
• SMILES: CC(C)(C(=O)OC)O

Properties

• Density: 1.03
• Boiling point: 137 °C
• Refractive index: 1.41-1.412
• Flash point: 41 °C

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Risk Statements: H226-H318
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264+P265-P271-P280-P303+P361+P353-P304+P340-P305+P354+P338-P317-P319-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

Methyl 2-hydroxyisobutyrate (M2HIB) is an ester that plays an important role in organic synthesis and various industrial applications. M2HIB is a derivative of isobutyric acid modified by the addition of a hydroxyl group and a methyl ester. While the exact historical details of its discovery are not well documented, the emergence of M2HIB as an industrial chemical likely occurred with the advancement of esterification processes and the growing demand for specialized intermediates in chemical manufacturing during the 20th century. Structurally, M2HIB consists of a methyl ester linked to hydroxylated isobutyric acid. This structure imparts unique reactivity, particularly in esterification and polymerization reactions.

M2HIB is widely used as a building block in organic synthesis. Its functional groups make it a versatile intermediate for the synthesis of a wide range of compounds, and M2HIB is a precursor for the synthesis of active pharmaceutical ingredients (APIs). Its role as a chiral auxiliary or intermediate aids in the production of pharmaceuticals, yielding stereoisomers with specific biological activities. In fine chemical production, M2HIB is used to manufacture complex molecules required for a variety of industrial and research applications. Its ability to participate in reactions such as esterification, transesterification, and acylation makes it a valuable reagent in chemical synthesis.

M2HIB is used to make specialty polymers and resins. It acts as a monomer or co-monomer during polymerization, which helps develop materials with tailored properties. M2HIB is used to synthesize acrylic resins, which are used in coatings, adhesives, and sealants. The resulting polymers exhibit desirable properties such as enhanced adhesion, flexibility, and chemical resistance. The ester functionality of M2HIB enables it to participate in polyester synthesis. Polyesters produced using M2HIB can be used to make fibers, films, and plastic parts, benefiting from the chemical stability and mechanical strength of the polymer.

In chemical research, M2HIB is used as a reagent and reference standard. Its well-characterized structure and reactivity make it a useful model compound for studying esterification reactions, mechanisms of organic transformations, and for developing new synthetic methods.

M2HIB is used in the flavor and fragrance industry for its pleasant odor and ester-like properties, as a flavoring and fragrance ingredient in a variety of consumer products, including perfumes, soaps, and food additives. Its role as a fragrance intermediate helps create complex scent profiles in perfumes and personal care products.

References

2024. Plastic-Derived Solid Acid Catalysts for the Production of Methyl 2-Hydroxyisobutyrate via Esterification. Korean Journal of Chemical Engineering, 41(7).
DOI: 10.1007/s11814-024-00154-w

2021. Production of Methacrylic Acid and Metacrylates. Catalysis in Industry, 13(2).
DOI: 10.1134/s2070050421020057

2006. Intra- vs. intermolecular hydrogen bonding: dimers of alpha-hydroxyesters with methanol. Physical Chemistry Chemical Physics, 8(37).
DOI: 10.1039/b609725a