Benzopinacole
[CAS# 464-72-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic alcohol
• Name: Benzopinacole
• Synonyms: 1,1,2,2-Tetraphenyl-1,2-ethanediol
• Molecular Formula: C₂₆H₂₂O₂
• Molecular Weight: 366.45
• CAS Registry Number: 464-72-2
• EC Number: 207-356-8
• SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C(C3=CC=CC=C3)(C4=CC=CC=C4)O)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 171-173 ºC (Expl.)
• Index of Refraction: 1.648, Calc.^*
• Boiling Point: 506.9±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 224.9±23.3 ºC, Calc.^*
• Water solubility: insoluble

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Hazard Statements: H302-H361-H372-H410
• Precautionary Statements: P201-P264-P280-P301+P330+P331-P312

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovory and Applicatios

Benzopinacole is an organic compound with the molecular formula C13H12, consisting of two benzene rings connected by a single carbon-carbon bond. It is a member of the pinacol class of compounds and is notable for its role as an intermediate in organic synthesis. Benzopinacole is typically obtained through the reduction of benzopinacol, a reaction that involves the transfer of two electrons to form a carbon-carbon bond.

Benzopinacole was first synthesized in the early 20th century as part of a series of studies aimed at understanding the chemistry of pinacol-type compounds. Its discovery and synthesis have since provided important insights into the mechanisms of radical reactions and electron transfer in organic chemistry. The compound is characterized by its crystalline form and is used primarily as an intermediate in the synthesis of various organic molecules.

In terms of applications, benzopinacole serves as a key precursor for the formation of other compounds, particularly those involving the introduction of aromatic rings or functional groups. It is often utilized in the preparation of chemical compounds used in materials science, organic electronics, and other advanced chemical applications. Benzopinacole’s structure and reactivity make it useful for the development of novel synthetic methodologies in the creation of more complex organic molecules.

Additionally, benzopinacole has been explored in the field of photochemistry. It is known to undergo photochemical reactions, such as photodimerization, in which two molecules of benzopinacole react under UV light to form a dimer. This process has been studied as a model for understanding reaction mechanisms in the presence of light. The photochemical behavior of benzopinacole contributes to its relevance in studies of molecular interactions and the behavior of organic compounds under light exposure.

The use of benzopinacole as an intermediate in organic synthesis has made it an important compound in both academic and industrial chemistry. Its ability to undergo further chemical transformations allows for the synthesis of a wide range of compounds with varied applications. Moreover, the compound is of interest in the context of organic synthesis for its potential in the development of new materials and in the study of molecular structures.

Overall, benzopinacole is a versatile and important compound in the field of organic chemistry, primarily due to its role as a precursor in the synthesis of other organic molecules. Its photochemical properties also make it significant for research in the field of photochemistry, and its applications continue to be explored in various chemical disciplines.

References

1960. Electrochemical method of studying the reactions of free ketyl radicals. Die Naturwissenschaften, 47(2).
DOI: 10.1007/bf00641119

2018. Magnetically hyper-cross-linked polymers with well-developed mesoporous: a broad-spectrum and highly efficient adsorbent for water purification. Journal of Materials Science, 53(2).
DOI: 10.1007/s10853-018-2967-z

2023. Electrochemically induced decomposition of benzopinacol. Russian Chemical Bulletin, 72(11).
DOI: 10.1007/s11172-023-4067-8