4-tert-Amylphenol
[CAS# 80-46-6]

Identification

• Classification: Natural product >> Natural phenols
• Name: 4-tert-Amylphenol
• Synonyms: 1-Hydroxy-4(2-methyl-2-butyl)benzene; p-(1,1-Dimethylpropyl)phenol
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.25
• CAS Registry Number: 80-46-6
• EC Number: 201-280-9
• SMILES: CCC(C)(C)C1=CC=C(C=C1)O

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*, 0.962 g/mL (Expl.)
• Melting point: 88 - 89 ºC (Expl.)
• Boiling point: 262.5 ºC 760 mmHg (Calc.)^*, 255 ºC (Expl.)
• Flash point: 122.4±8.2 ºC (Calc.)^*
• Index of refraction: 1.51 (Calc.)^*
• Water solubility: 37 mg/L (20 ºC)

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

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Hazard Statements: H302-H312-H314-H317-H318-H410-H411
• Precautionary Statements: P260-P261-P264-P264+P265-P270-P272-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P333+P317-P362+P364-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin sensitization	Skin Sens.	1B	H317
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H332
Skin corrosion	Skin Corr.	1A	H314
Skin corrosion	Skin Corr.	1C	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 2430

Discovory and Applicatios

4-tert-Amylphenol is an organic compound classified as a substituted phenol, characterized by a tert-amyl group attached to the para position of the phenol ring. It is one of several alkylphenols derived from phenol by alkylation, where the tert-amyl substituent consists of a branched five-carbon alkyl chain.

The compound was identified through synthetic organic chemistry research focusing on the modification of phenol derivatives to explore their chemical and physical properties. Its preparation typically involves the alkylation of phenol using suitable reagents that introduce the tert-amyl group in the para position, favoring regioselectivity due to steric and electronic effects.

4-tert-Amylphenol exhibits typical phenolic properties such as acidity and the ability to participate in hydrogen bonding. The presence of the bulky tert-amyl group influences its solubility, melting point, and reactivity compared to unsubstituted phenol and other alkylphenols. These structural features affect its behavior in chemical reactions and applications.

This compound is mainly used as an intermediate in organic synthesis, where it serves as a building block for the production of more complex molecules. Its phenolic hydroxyl group allows for further functionalization, including etherification, esterification, and coupling reactions, making it valuable in the manufacture of specialty chemicals.

In industrial applications, 4-tert-amylphenol is utilized in the synthesis of antioxidants, stabilizers, and corrosion inhibitors. Its derivatives contribute to the enhancement of polymer stability and performance, protecting materials from degradation caused by heat, oxygen, and other environmental factors.

Additionally, 4-tert-amylphenol finds use in the preparation of pharmaceuticals and agrochemicals, where its phenolic structure serves as a scaffold for biologically active compounds. The compound’s chemical versatility facilitates the development of molecules with desired biological properties.

Safety considerations for 4-tert-amylphenol include its classification as a hazardous substance due to its phenolic nature, which can cause skin and eye irritation upon exposure. Proper handling and protective measures are necessary during its synthesis and use in industrial settings.

In summary, 4-tert-amylphenol is a phenolic compound with a tert-amyl substituent at the para position, discovered through synthetic organic chemistry approaches. Its applications span organic synthesis, industrial additive production, and chemical intermediate use, leveraging its structural and reactive properties in various chemical manufacturing processes.

References

1960. Catalytic synthesis of 2,4-di-tert-amylphenol. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science, 9(8).
DOI: 10.1007/bf00907678

1982. Binding of Selected Phenol Derivatives to Human Serum Proteins. Journal of Pharmaceutical Sciences, 71(10).
DOI: 10.1002/jps.2600711017

2018. 4-tert-Pentylphenoxyalkyl derivatives � Histamine H3 receptor ligands and monoamine oxidase B inhibitors. Bioorganic & Medicinal Chemistry Letters, 28(23-24).
DOI: 10.1016/j.bmcl.2018.10.048