2-Phenyl-1,3-propanediol
[CAS# 1570-95-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic alcohol
• Name: 2-Phenyl-1,3-propanediol
• Synonyms: 2-Phenylpropane-1,3-diol
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• CAS Registry Number: 1570-95-2
• EC Number: 411-810-2
• SMILES: C1=CC=C(C=C1)C(CO)CO

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 53-56 ºC (Expl.)
• Index of Refraction: 1.56, Calc.^*
• Boiling Point: 310.6±22.0 ºC (760 mmHg), Calc.^*
• Flash Point: 153.8±16.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H318
• Precautionary Statements: P264+P265-P280-P305+P354+P338-P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

2-Phenyl-1,3-propanediol is an organic compound with the molecular formula C9H12O2. It is a diol, specifically a hydroxyalkyl phenyl compound, consisting of a phenyl group attached to the second carbon of a 1,3-propanediol backbone. This structure gives the compound two hydroxyl groups, one on each of the first and third carbon atoms of the propylene chain.

2-Phenyl-1,3-propanediol was first synthesized in the early 20th century as part of efforts to explore various hydroxyalkyl derivatives for their potential applications. Since its discovery, the compound has been studied for its reactivity and functional properties, particularly in the context of polymer chemistry and fine chemicals.

The primary application of 2-Phenyl-1,3-propanediol is in the synthesis of various specialty chemicals, particularly as a building block in the production of high-performance polymers, resins, and plastics. The presence of the hydroxyl groups in the molecule allows it to be involved in esterification and polymerization reactions. Its phenyl group also imparts certain stability and rigidity to the polymers and resins derived from it. The compound is used as a precursor in the preparation of polyesters and polyurethanes, where its dual hydroxyl functionality contributes to the material's overall mechanical properties and resistance to degradation.

2-Phenyl-1,3-propanediol also finds use in the synthesis of fragrances and flavoring agents. It is a key ingredient in the production of certain esters, which are commonly used in the fragrance industry due to their pleasant floral or fruity odors. The compound is considered important for the creation of synthetic aromas and is incorporated into various fragrance compositions for its ability to add complexity to the overall scent profile.

In the pharmaceutical industry, 2-Phenyl-1,3-propanediol has been explored for its potential as a precursor in the synthesis of active pharmaceutical ingredients (APIs). Its hydroxyl groups and aromatic structure offer opportunities for modification to create compounds with biological activity, although its primary use in this field remains focused on its chemical utility as an intermediate.

Due to its relatively simple structure and the versatility of its reactivity, 2-Phenyl-1,3-propanediol is also used in various organic syntheses. It serves as an intermediate in the preparation of other important chemicals and compounds, where the phenyl and hydroxyl groups can be further modified to yield derivatives with diverse chemical properties.

In summary, 2-Phenyl-1,3-propanediol is a valuable chemical intermediate widely used in the synthesis of polymers, resins, fragrances, and other organic compounds. Its reactivity and structural characteristics make it an important building block in the chemical industry, with applications in both fine chemicals and materials science.

References

2007. Site-Specific and Asymmetric Hydrolysis of Prochiral 2-Phenyl-1,3-propanediol Diacetate by a Bacterial Esterase from an Isolated Strain. Bioscience, Biotechnology, and Biochemistry, 71(8).
DOI: 10.1271/bbb.70019

2007. Fluorofelbamate. Neurotherapeutics, 4(1).
DOI: 10.1016/j.nurt.2006.11.015

2021. Characterization and In-silico toxicity prediction of degradation products of felbamate. Future Journal of Pharmaceutical Sciences, 7(1).
DOI: 10.1186/s43094-021-00347-8