4-tert-Butylbenzoic acid
[CAS# 98-73-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 4-tert-Butylbenzoic acid
• Synonyms: PTBBA
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• CAS Registry Number: 98-73-7
• EC Number: 202-696-3
• SMILES: CC(C)(C)C1=CC=C(C=C1)C(=O)O

Properties

• Water solubility: 0.07 g/L (20 °C)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 162-165 °C
• Index of Refraction: 1.524, Calc.^*
• Boiling Point: 283.3±19.0 °C (760 mmHg), Calc.^*, 280 °C
• Flash Point: 134.9±16.2 °C, Calc.^*, 158 °C

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H360-H360F-H361-H372-H373-H411
• Safety Statements: P203-P260-P264-P270-P273-P280-P301+P317-P318-P319-P330-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Repr.	1B	H360F
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	4	H312
Reproductive toxicity	Repr.	1A	H360
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	1	H370
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H411
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	1B	H360F

• Transport Information: UN 2811

Discovery and Applications

4-tert-Butylbenzoic acid is an aromatic carboxylic acid that belongs to the family of benzoic acids. It is characterized by a tert-butyl group attached to the para position of the benzoic acid structure, giving it unique properties that have made it a subject of interest in various fields. The discovery of 4-tert-butylbenzoic acid dates back to the early 20th century when scientists were exploring the chemical properties and potential applications of substituted benzoic acids. Its synthesis typically involves the alkylation of benzoic acid with tert-butyl halides, a method that allows for the efficient introduction of the bulky tert-butyl group.

One of the primary applications of 4-tert-butylbenzoic acid is in the field of organic synthesis, where it serves as an intermediate in the production of various chemical compounds. It is widely utilized in the synthesis of pharmaceuticals, agrochemicals, and other organic materials due to its ability to undergo various chemical reactions, including esterification and amidation. This versatility makes it an essential building block in the development of more complex molecules.

In the realm of materials science, 4-tert-butylbenzoic acid is employed as a stabilizer for polymers. Its presence can improve the thermal stability of polymers, making them suitable for applications that require materials to withstand high temperatures. This property is particularly beneficial in the production of high-performance plastics and elastomers, where thermal degradation can significantly affect the material's integrity and performance.

Another notable application of 4-tert-butylbenzoic acid is in the cosmetics industry. Due to its mildness and compatibility with various formulations, it is often used as a pH adjuster and stabilizer in cosmetic products. Its inclusion helps maintain the stability and efficacy of active ingredients, contributing to the overall performance of skin care and cosmetic formulations.

The safety of 4-tert-butylbenzoic acid has been a point of consideration in its application. While it is generally regarded as safe for use in various industries, regulatory assessments have been conducted to ensure that it does not pose significant health risks when used in appropriate concentrations. Manufacturers are advised to adhere to established safety guidelines to minimize any potential adverse effects.

Recent studies have begun to explore the potential of 4-tert-butylbenzoic acid in novel applications, including its use in drug delivery systems and as a precursor for functional materials. Researchers are investigating its efficacy in enhancing the bioavailability of certain drugs and its role in the development of advanced materials with specific functional properties.

In summary, 4-tert-butylbenzoic acid is a valuable compound with diverse applications in organic synthesis, materials science, and cosmetics. Its unique properties derived from the tert-butyl substituent contribute to its versatility and effectiveness in various formulations. As research continues to uncover new applications, 4-tert-butylbenzoic acid is poised to remain a significant player in the chemical industry.

References

2022. Aerobic Photooxidation of Toluene Derivatives into Carboxylic Acids with Bromine-Water under Catalyst-Free Conditions. Synlett, 33(12).
DOI: 10.1055/a-1887-7885

2020. Discovery of Novel Peptidomimetic Boronate ClpP Inhibitors with Noncanonical Enzyme Mechanism as Potent Virulence Blockers in Vitro and in Vivo. Journal of Medicinal Chemistry, 63(3).
DOI: 10.1021/acs.jmedchem.9b01746

2022. Towards the mechanism of spermatotoxicity of p-tert-butyl-alpha-methylhydrocinnamic aldehyde: inhibition of late stage ex-vivo spermatogenesis in rat seminiferous tubule cultures by para-tert-butyl- benzoic acid. Archives of Toxicology, 96(10).
DOI: 10.1007/s00204-022-03379-y