1,3-Diisopropenylbenzene
[CAS# 3748-13-8]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Aromatic hydrocarbon
• Name: 1,3-Diisopropenylbenzene
• Synonyms: 1,3-bis(prop-1-en-2-yl)benzene
• Molecular Formula: C₁₂H₁₄
• Molecular Weight: 158.24
• CAS Registry Number: 3748-13-8
• EC Number: 223-146-9
• SMILES: CC(=C)C1=CC(=CC=C1)C(=C)C

Properties

• Solubility: 4.633 mg/L (25 ºC water)
• Density: 0.9±0.1 g/cm³, Calc.^*, 0.925 g/mL
• Index of Refraction: 1.516, Calc.^*, 1.556
• Melting point: -13.95 ºC
• Boiling Point: 231.0±0.0 ºC (760 mmHg), Calc.^*, 216.51 ºC
• Flash Point: 91.1±0.0 ºC, Calc.^*, 93 ºC

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H315-H317-H319-H335-H400-H411
• Precautionary Statements: P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	2	H300

Discovory and Applicatios

1,3-Diisopropenylbenzene is an aromatic hydrocarbon with the molecular formula C₁₂H₁₄, consisting of a benzene ring substituted with two isopropenyl groups at the 1 and 3 positions. This compound belongs to the family of diisopropenylbenzenes, with structural characteristics that make it useful in polymer chemistry and industrial synthesis.

The compound is typically obtained through alkylation reactions involving benzene derivatives and propylene or isopropenyl intermediates. The synthesis may also involve the dehydrogenation of corresponding diisopropylbenzene compounds. The structural configuration of the isopropenyl substituents contributes to the compound's ability to undergo further chemical transformations, particularly in polymerization.

1,3-Diisopropenylbenzene is primarily used as a comonomer in the production of thermosetting resins and polymers. It serves as a crosslinking agent in the manufacture of specialty polymers due to its two reactive vinyl groups, which can participate in radical polymerization processes. These applications are relevant in producing materials that require enhanced mechanical strength, chemical resistance, or thermal stability.

In industrial applications, it is also employed in the synthesis of high-performance resins for coatings, adhesives, and sealants. Its inclusion in polymeric systems can improve rigidity and crosslink density, which are desirable in applications where structural durability is essential.

Moreover, the compound has been studied for its role in the development of polymer networks for ion-exchange resins and as a precursor in the synthesis of complex organic materials. Its reactivity profile allows it to be functionalized further or incorporated into more elaborate chemical architectures.

Due to the presence of the isopropenyl groups, 1,3-diisopropenylbenzene is sensitive to oxidation and polymerization under certain conditions, necessitating appropriate storage and handling to prevent premature reaction. It is generally handled under inert conditions or in the presence of inhibitors when stored for long periods.

Overall, 1,3-diisopropenylbenzene is a well-established compound in polymer and materials chemistry, valued for its dual unsaturated groups that enable crosslinking and structural integration in advanced synthetic materials.

References

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DOI: 10.1007/s11356-024-32323-z

2023. Reverse Vulcanization of Monomers with Conjugated Bonds Double and Elemental Sulfur for S�S Bond Self-Healing Properties. Polymer Science, Series B, 65(6).
DOI: 10.1134/s1560090423600274

2023. Organosulfur Polymer Composites by Free Radical Polymerization of Sulfur with Vegetable Oils. Advances in Material Research and Technology, Chapter 18.
DOI: 10.1007/978-3-031-42731-2_18