Cumyl hydroperoxide
[CAS# 80-15-9]

Identification

• Classification: Organic raw materials >> Organic sulfur compound
• Name: Cumyl hydroperoxide
• Synonyms: 1-Mmethyl-1-phenylethylhydroperoxide; alpha,alpha-Dimethylbenzylhydroperoxide; Cumene hydroperoxide
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• CAS Registry Number: 80-15-9
• EC Number: 201-254-7
• SMILES: CC(C)(C1=CC=CC=C1)OO

Properties

• Density: 1.038
• Melting point: -30 °C
• Boiling point: 153 °C
• Flash point: 83 °C
• Water solubility: Slightly soluble

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS08;GHS05;GHS09 Danger
• Risk Statements: H242-H302-H312-H314-H317-H318-H331-H341-H373-H411
• Safety Statements: P203-P210-P234-P235-P240-P260-P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P318-P319-P321-P330-P333+P317-P362+P364-P363-P370+P378-P391-P403-P403+P233-P405-P410-P411-P420-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin corrosion	Skin Corr.	1B	H314
Organic peroxides	Org. Perox.	E	H242
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H312
Serious eye damage	Eye Dam.	1	H318
Germ cell mutagenicity	Muta.	2	H341
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Specific target organ toxicity - single exposure	STOT SE	2	H371
Flammable liquids	Flam. Liq.	3	H226
Organic peroxides	Org. Perox.	F	H242
Skin corrosion	Skin Corr.	1	H314
Self-reactive substances or mixtures	Self-react.	E	H242
Acute toxicity	Acute Tox.	2	H310
Skin sensitization	Skin Sens.	1B	H317

• Transport Information: UN 2116; UN 3109

Discovery and Applications

Cumyl hydroperoxide, also known as 1-phenyl-1-(peroxy)propan-2-ol, is a chemical compound with significant industrial and research applications. It was first synthesized in the early 20th century and has since become an important reagent in various chemical processes.

The discovery of cumyl hydroperoxide can be traced back to the early work on peroxides and hydroperoxides, which are known for their reactivity and role as oxidizing agents. Cumyl hydroperoxide was developed as part of research into new peroxide compounds that could be used in polymerization and oxidation reactions. Its unique properties, including its stability and ability to decompose to release free radicals, made it a valuable tool in chemical synthesis.

Cumyl hydroperoxide is primarily used as a polymerization initiator. In polymer chemistry, it serves as a radical initiator in the polymerization of various monomers, including styrene and acrylates. Its ability to generate free radicals upon decomposition makes it an effective catalyst for initiating polymerization reactions. This application is crucial in the production of plastics, resins, and other polymeric materials, where controlled polymerization is necessary to achieve desired material properties.

In addition to its role in polymerization, cumyl hydroperoxide is used in the oxidation of organic compounds. It acts as an oxidizing agent in various chemical reactions, including the oxidation of alkenes to ketones and aldehydes. This application is valuable in synthetic organic chemistry, where precise oxidation reactions are required to produce specific chemical compounds.

Cumyl hydroperoxide also finds use in the synthesis of other chemicals. It is employed in the production of certain pharmaceuticals and agrochemicals, where its reactivity and ability to introduce functional groups into molecules are utilized. Its role in these processes highlights its versatility and importance in industrial chemistry.

Despite its utility, cumyl hydroperoxide must be handled with care due to its reactive nature. It is a strong oxidizing agent and can be hazardous if not managed properly. Safety precautions are necessary to prevent accidents and ensure safe handling in industrial and laboratory settings.

Overall, cumyl hydroperoxide is a valuable chemical with diverse applications in polymer chemistry, oxidation reactions, and chemical synthesis. Its discovery and development have made significant contributions to various fields, demonstrating its importance in both industrial and research contexts.

References

1994. Lipid hydroperoxides evoke antigonototropic and antisteroidogenic activity in rat luteal cells. Endocrinology, 135(6).
DOI: 10.1210/en.135.6.2723

1984. Hydroperoxides as inactivators of aromatase: 10.beta.-hydroperoxy-4-estrene-3,17-dione, crystal structure and inactivation characteristics. Biochemistry, 23(22).
DOI: 10.1021/bi00318a004

2024. Triphenylphosphine in the identification of oxidation products of organic compounds with molecular oxygen and peroxides. Russian Chemical Bulletin, 73(9).
DOI: 10.1007/s11172-024-4367-7