4-tert-Butoxystyrene
[CAS# 95418-58-9]

Identification

• Classification: Organic raw materials >> Aryl compounds
• Name: 4-tert-Butoxystyrene
• Synonyms: 1-(Tert-butoxy)-4-ethenylbenzene
• Molecular Formula: C₁₂H₁₆O
• Molecular Weight: 176.26
• CAS Registry Number: 95418-58-9
• EC Number: 619-127-3
• SMILES: CC(C)(C)OC1=CC=C(C=C1)C=C

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.936 g/mL (Expl.)
• Melting point: -38 °C (Expl.)
• Index of Refraction: 1.523, Calc.^*, 1.524 (Expl.)
• Boiling Point: 256.8±9.0 °C (760 mmHg), Calc.^*, 356.4-358.1 °C (Expl.)
• Flash Point: 97.1±8.0 °C, Calc.^*, 97 °C (Expl.)

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

Safety Data

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

Hazard Classification

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

Discovery and Applications

4-tert-Butoxystyrene is an organic compound that is primarily used as a monomer in the production of polymers and copolymers. It is a derivative of styrene, where the hydrogen atom at the para-position of the benzene ring is replaced by a tert-butoxy group (–OC4H9). The tert-butoxy group provides steric hindrance, which can influence the reactivity and properties of the compound, particularly in polymerization reactions.

The discovery of 4-tert-butoxystyrene can be traced to the broader investigation of substituted styrenes, which have been studied for their ability to undergo polymerization reactions. Substituted styrenes, including 4-tert-butoxystyrene, have attracted attention due to their ability to yield polymers with unique properties compared to unmodified styrene. The tert-butoxy group is particularly useful in controlling the polymerization process and in modifying the solubility, mechanical properties, and thermal stability of the resulting polymers.

4-tert-Butoxystyrene is commonly synthesized by the electrophilic aromatic substitution of styrene with tert-butyl alcohol in the presence of an acid catalyst, such as sulfuric acid. The reaction selectively introduces the tert-butoxy group at the para-position of the styrene ring. This synthesis route has been extensively studied and is well-established in organic chemistry. In addition, the use of tert-butyl peroxides as initiators in polymerization reactions is a typical method for producing polymers from 4-tert-butoxystyrene.

One of the main applications of 4-tert-butoxystyrene is in the production of high-performance polymers. The presence of the bulky tert-butoxy group can impart desirable properties to the polymer, such as increased thermal stability, enhanced solubility in nonpolar solvents, and improved mechanical strength. Polymers made from 4-tert-butoxystyrene are often used in coatings, adhesives, and composite materials. These materials are useful in industries ranging from automotive to electronics, where high-performance materials with tailored properties are required.

Another important application of 4-tert-butoxystyrene is in the synthesis of functional copolymers. By copolymerizing 4-tert-butoxystyrene with other monomers, such as styrene, methyl methacrylate, or acrylonitrile, it is possible to create copolymers with varying degrees of polarity, flexibility, and rigidity. These copolymers can be designed for specific applications, including in biomedical devices, packaging materials, and as advanced engineering plastics.

Furthermore, 4-tert-butoxystyrene is also of interest in research applications, particularly in the fields of material science and polymer chemistry. The steric effects of the tert-butoxy group on polymerization kinetics and the structure of the resulting polymer chains have been subjects of study in academic research. These studies help scientists understand the relationship between monomer structure and polymer properties, aiding in the design of new materials for various applications.

In summary, 4-tert-butoxystyrene is an important chemical used primarily in the production of specialized polymers and copolymers. Its discovery and development have contributed to the broader field of polymer chemistry, providing a means to tailor the properties of materials for specific industrial and research purposes. The compound's role in enhancing polymer stability and performance continues to be a valuable tool in both applied and academic settings.

References

1990. Synthesis of block copolymers of p-methoxystyrene and vinyl ethers by the hydrogen iodide/zinc iodide initiating system. Polymer Bulletin, 24(2).
DOI: 10.1007/bf00338494

2011. Micelle formation of polystyrene-block-poly(4-tert-butoxystyrene) in hexane. Colloid and Polymer Science, 289(15-16).
DOI: 10.1007/s00396-011-2411-2

2019. Palladium/Copper Catalysis for Hydroarylation. Science of Synthesis.