Ethyl 3-mercaptopropionate
[CAS# 5466-06-8]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Aliphatic carboxylate
• Name: Ethyl 3-mercaptopropionate
• Synonyms: 3-Mercaptopropionic acid ethyl ester
• Molecular Formula: C₅H₁₀O₂S
• Molecular Weight: 134.20
• CAS Registry Number: 5466-06-8
• EC Number: 226-771-5
• FEMA: 3677
• SMILES: CCOC(=O)CCS

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 194.3 °C 760 mmHg (Calc.)^*, 217.3 - 218.7 °C (Expl.)
• Flash point: 72.8 °C (Calc.)^*
• Index of refraction: 1.455 (Calc.)^*, 1.457 (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Flammable liquids	Flam. Liq.	4	H227

Discovery and Applications

Ethyl 3-mercaptopropionate is an organic compound belonging to the class of thiol esters. It is composed of an ethyl ester group (-COOCH2CH3) attached to the sulfur-containing mercaptopropionate moiety (C3H5O2S). The structure consists of a three-carbon chain, where the central carbon is bonded to a thiol group (-SH) at the 3-position, and the terminal carboxyl group is esterified with an ethyl group.

This compound is significant due to the presence of both the mercapto group (-SH) and the ester functional group, which imparts unique reactivity and properties to the molecule. The mercapto group is highly nucleophilic, making it reactive in a wide range of chemical reactions. This reactivity is often exploited in the synthesis of various other chemical compounds, particularly in processes involving thiol-based nucleophilic substitution or thiol-disulfide exchange reactions.

Ethyl 3-mercaptopropionate has several applications in different chemical and industrial sectors. It is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and specialty chemicals. Its thiol group makes it a useful precursor in the production of thiol-functionalized materials, such as polymers and other materials that require sulfur-containing functional groups.

In addition to its use in organic synthesis, ethyl 3-mercaptopropionate has been studied for its potential biological activities. Thiol esters, such as this compound, are often investigated for their antioxidant, anti-inflammatory, and antimicrobial properties. The mercapto group plays a key role in mediating such activities by interacting with free radicals or by forming coordination complexes with metal ions, which may enhance the compound's biological effects.

Furthermore, ethyl 3-mercaptopropionate can be employed in the preparation of thiol-based reagents for use in the preparation of peptide-based compounds or in other synthetic chemistry reactions that require thiol groups for cross-linking or modification.

In the field of materials science, the sulfur-containing structure of ethyl 3-mercaptopropionate also makes it an important component for the design of functional materials. It can be used in the synthesis of materials with self-assembling or adhesive properties, or in the modification of surfaces to improve their chemical resistance or stability.

Overall, ethyl 3-mercaptopropionate is a versatile compound with numerous applications in organic synthesis, biological studies, and materials science, driven by the reactivity and versatility of its thiol and ester groups.