(R)-(+)-2-Tetrahydrofuroic acid
[CAS# 87392-05-0]

Identification

• Name: (R)-(+)-2-Tetrahydrofuroic acid
• Synonyms: (R)-(+)-Tetrahydro-2-furoic acid
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.12
• CAS Registry Number: 87392-05-0
• EC Number: 627-523-2
• SMILES: C1C[C@@H](OC1)C(=O)O

Properties

• Density: 1.209 g/mL (Expl.)
• Melting point: 21 °C (Expl.)
• Boiling point: 128-129 °C (13 mmHg) (Expl.)
• alpha: 4 (Expl.)
• Refractive index: 1.46 (Expl.)
• Flash Point: 139 °C (Expl.)

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314
• Safety Statements: P260-P264-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314

• Transport Information: UN 3265

Discovery and Applications

(R)-(+)-2-Tetrahydrofuroic acid is a chiral organic compound that plays an important role in the field of asymmetric synthesis. It is derived from tetrahydrofuran, a common cyclic ether, and is characterized by the presence of a carboxylic acid group at the 2-position of the tetrahydrofuran ring. The (R)-(+)-configuration refers to the specific three-dimensional arrangement of atoms around the chiral center, which imparts particular stereochemical properties to the compound. The discovery of (R)-(+)-2-tetrahydrofuroic acid emerged from ongoing studies of furan derivatives and their potential applications in catalysis and synthesis, especially in the creation of stereochemically defined compounds.

The synthesis of (R)-(+)-2-tetrahydrofuroic acid typically involves the asymmetric hydrolysis of epoxides or other starting materials that lead to the formation of tetrahydrofuran rings with functional groups at the desired positions. One widely employed method is the use of chiral reagents or catalysts to induce stereoselectivity, allowing the generation of the (R)-isomer. This process is often carried out under controlled conditions to ensure high yields and purity, as the enantiomeric form of the compound can have significantly different chemical properties and biological activities.

(R)-(+)-2-tetrahydrofuroic acid finds applications in a variety of fields, most notably in the synthesis of biologically active molecules and pharmaceuticals. Its chiral nature makes it a useful building block in the design of drugs that require specific stereochemistry for optimal activity. For instance, it can serve as an intermediate in the synthesis of peptide-based drugs or as a precursor to other furan derivatives that exhibit pharmacological effects. The compound has been studied for its potential in the development of anti-inflammatory and anti-cancer agents, as well as in the creation of novel antibiotics and antivirals.

In addition to its pharmaceutical applications, (R)-(+)-2-tetrahydrofuroic acid is also employed in the field of materials science. Its unique structure enables it to participate in the formation of polymeric materials, which can be used in a range of applications from coatings to electronic devices. The compound's ability to undergo specific reactions, such as esterification and nucleophilic substitution, makes it a valuable intermediate in the synthesis of polymers with desired properties.

(R)-(+)-2-tetrahydrofuroic acid is also gaining attention in the area of green chemistry, where it is being explored for use in environmentally friendly catalytic processes. The compound's ability to act as a ligand in metal-catalyzed reactions has led to its incorporation in several catalytic cycles that promote selective transformations while minimizing waste and energy consumption. This makes (R)-(+)-2-tetrahydrofuroic acid an attractive choice for sustainable chemistry applications.

In summary, (R)-(+)-2-tetrahydrofuroic acid is a versatile and valuable chemical compound in the fields of asymmetric synthesis, pharmaceuticals, materials science, and green chemistry. Its chiral nature and unique reactivity make it a key intermediate in the synthesis of complex molecules with specific stereochemical properties, and its ongoing exploration in various industrial applications underscores its potential in future research and development.

References

2021. Truncated Mycalolide B Analog to Prevent Cancer Metastasis. Synfacts, 17(8).
DOI: 10.1055/s-0040-1720781

2009. Highly Diastereoselective Hydrogenation of Furan-2-carboxylic Acid Derivatives on Heterogeneous Catalysts. Synlett, 2009(2).
DOI: 10.1055/s-0028-1087532

2006. Drugs, their targets and the nature and number of drug targets. Nature reviews. Drug discovery, 5(10).
DOI: 10.1038/nrd2132