(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol
[CAS# 14347-78-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol
• Synonyms: (-)-2,3-O-Isopropylidene-sn-glycerol; (R)-(-)-Solketal
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• CAS Registry Number: 14347-78-5
• EC Number: 604-360-5
• SMILES: CC1(OC[C@H](O1)CO)C

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*, 1.066 g/mL (Expl.)
• Boiling point: 188.5 ºC 760 mmHg (Calc.)^*, 220.2 - 221.6 ºC (Expl.)
• Flash point: 80.0 ºC (Calc.)^*, 80 ºC (Expl.)
• Index of refraction: 1.424 (Calc.)^*, 1.434 (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 WarningGHS02
• Hazard Statements: H227-H302-H315-H319-H335
• Precautionary Statements: P210-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403-P403+P233-P405-P501

Hazard Classification

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

Discovory and Applicatios

(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol is a chemical compound that belongs to the class of dioxolanes, which are cyclic ethers containing two oxygen atoms in the ring. It has a specific stereochemistry, denoted as (R)-(-), which indicates that it is the enantiomer with a particular spatial configuration at the chiral centers. This compound has several applications, primarily in organic synthesis and medicinal chemistry.

The discovery and application of (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol have been tied to its use as a chiral building block in the synthesis of various organic molecules. The presence of the chiral center and the methanol group attached to the dioxolane ring provide a structural framework that allows it to participate in stereoselective reactions. In particular, this compound is valuable in the synthesis of complex molecules where control over the stereochemistry is essential.

One of the key applications of (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol is its role as a chiral auxiliary in asymmetric synthesis. In many chemical reactions, controlling the configuration of the products is important, especially when synthesizing molecules that are required to have a specific three-dimensional arrangement of atoms. The compound can be used to induce chirality in reactions where the desired outcome is a specific stereoisomer. This makes it a valuable tool in the synthesis of pharmaceuticals, agrochemicals, and other biologically active compounds.

Moreover, (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol is utilized in the preparation of other chiral molecules through stereoselective reactions such as nucleophilic substitution, reduction, and addition reactions. The ability of the compound to direct the stereochemistry of these reactions can be harnessed to obtain compounds with the desired stereochemical configuration, which is particularly important in the production of drugs with high selectivity for biological targets.

Additionally, the methanol group in the compound may participate in hydrogen bonding interactions, further influencing the reactivity of (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol in various chemical environments. This property allows for its use in selective transformations where other functionalities in the molecule or substrate may be sensitive to environmental factors.

The compound's structure also lends itself to being incorporated into more complex molecular frameworks. Due to its cyclic nature and the presence of oxygen atoms in the ring, it can be part of the synthesis of larger molecules, including those with potential applications in materials science and drug development.

In medicinal chemistry, (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol may be used as an intermediate in the synthesis of compounds that exhibit pharmacological activity. The ability to manipulate its stereochemistry allows chemists to create compounds with specific binding affinities and selectivity for biological targets, which is a crucial factor in drug design.

Although the direct use of (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol in commercial products is not as widespread as some other chiral auxiliaries, its role as an intermediate or building block in organic synthesis makes it important in the development of new chemical entities and materials. As research into stereoselective reactions and chiral chemistry advances, the compound's application may expand, particularly in the field of green chemistry and sustainable synthesis methods.

In conclusion, (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol is a versatile and valuable compound in organic synthesis, especially for its role in stereoselective reactions and as a chiral auxiliary. Its applications extend to the synthesis of pharmaceuticals, agrochemicals, and other biologically active compounds, contributing to the development of molecules with specific properties and functions.

References

1980. A simplified procedure for the preparation of 2,3-O-isopropylidene-sn-glycerol from L-arabinose. Journal of Lipid Research, 21(2).
DOI: 10.1016/s0022-2275(20)39832-1

2006. Fourier transform near-infrared vibrational circular dichroism used for on-line monitoring the epimerization of 2,2-dimethyl-1,3-dioxolane-4-methanol: A pseudo racemization reaction. Chirality, 18(1).
DOI: 10.1002/chir.20263

2008. Resolution of (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-036-00285