2-(Hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol
[CAS# 91648-24-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: 2-(Hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol
• Synonyms: 2,2-Bis(hydroxymethyl)-1,3-propanediol allyl ether; Allyl Pentaerythritol
• Molecular Formula: C₈H₁₆O₄
• Molecular Weight: 176.21
• CAS Registry Number: 91648-24-7
• EC Number: 293-883-9
• SMILES: C=CCOCC(CO)(CO)CO

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.496, Calc.^*
• Boiling Point: 343.3±37.0 ºC (760 mmHg), Calc.^*
• Flash Point: 161.4±26.5 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

2-(Hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol is an organic compound that plays an essential role in the production of polymer resins and other materials where its chemical reactivity and multifunctional structure are exploited. It consists of a propane-1,3-diol backbone with hydroxymethyl groups and an allyl ether functionality, making it a versatile chemical in various polymerization reactions.

The compound was discovered as part of research into multifunctional monomers that can introduce crosslinking into polymer structures. Its development was driven by the need to enhance the mechanical properties and durability of polymer-based materials. The reactive hydroxyl and allyl groups in the molecule allow it to participate in a wide range of polymerization reactions, including free-radical, cationic, and anionic polymerizations, making it suitable for producing complex, crosslinked polymers.

One of the primary applications of 2-(Hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol is in the formulation of ultraviolet (UV) curable resins. These resins are used in coatings, adhesives, and inks that require fast curing times and robust mechanical properties. The allyl ether group in the compound is particularly useful for crosslinking under UV light, making it a key ingredient in the production of UV-cured materials. These materials are highly valued for their durability, resistance to chemicals, and environmental stability.

In addition to UV-curable systems, the compound is also utilized in the synthesis of thermosetting resins. Its hydroxyl groups can react with a variety of crosslinkers, including isocyanates and epoxides, to form strong, three-dimensional networks. This property makes it an important component in coatings and adhesives that need high thermal and mechanical resistance, such as those used in automotive and aerospace applications.

The multifunctionality of 2-(Hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol also makes it valuable in the production of hydrogels and other materials with tunable mechanical properties. Its hydroxyl groups can undergo esterification or etherification, allowing for the introduction of additional functionalities into the polymer network. This versatility has led to its use in biomedical applications, such as drug delivery systems, where controlled release and biocompatibility are critical.