4197-70-0

Usage

Uses

Used in Polymer Production:
2-butyl-p-benzoquinone is utilized as a polymerization inhibitor for the manufacturing of polymers such as acrylics, vinyl acetate, and styrene. It functions by initiating a reaction that hinders the formation of polymers, thus controlling the polymerization process during production.
Used in the Food Industry:
In the food sector, 2-butyl-p-benzoquinone serves as an antioxidant, playing a crucial role in preventing the oxidation of fats and oils. This helps in maintaining the quality, taste, and shelf life of food products by reducing the risk of rancidity and spoilage.

InChI:InChI=1/C10H12O2/c1-2-3-4-8-7-9(11)5-6-10(8)12/h5-7H,2-4H2,1H3

Upstream product

• 4197-69-7 4-(2,5-dihydroxyphenyl)butane 
• 57314-83-7 2-butyl-1,4-dimethoxy-benzene 
• 4426-47-5 butylboronic acid 
• 106-51-4 p-benzoquinone 

Relevant academic research and scientific papers

Substituent effects in the oxidation of 2-alkyl-1,4-dialkoxybenzenes with ceric ammonium nitrate

Increased steric size of alkyl groups and the presence of coordinating atoms on alkoxy groups have both been found to contribute to decreasing yields of diquinones upon reaction of 2-alkyl-1,4-dialkoxybenzenes with CAN. The overall hydrophilicity of the substrates does not appear to be a significant factor in determining the diquinone yield for these reactions.

Effects of reaction conditions on quinone/diquinone product ratios in the oxidation of 1,4-dimethoxybenzene derivatives with ceric ammonium nitrate

Proper choice of reaction conditions allows formation of either the quinone or corresponding diquinone as the major product upon treatment of 2-alkyl-1,4-dimethoxybenzenes with ceric ammonium nitrate.

Synthesis of aryl- and alkylquinones through rhodium-catalyzed C-C coupling under mild conditions

A direct arylation, alkylation of quinones with aryl and alkyl boronic acids through rhodium-catalyzed C-C coupling has been developed under mild conditions. [CpRhCl2]2 was shown to be the most effective catalyst for the transformation. More importantly, good to excellent yields were obtained under room temperature and base-free conditions. This reaction provides a practical, efficient method for the synthesis of aryl- and alkylquinones.

Practical C-H functionalization of quinones with boronic acids

A direct functionalization of a variety of quinones with several boronic acids has been developed. This scalable reaction proceeds readily at room temperature in an open flask using inexpensive reagents: catalytic silver(I) nitrate in the presence of a persulfate co-oxidant. The scope with respect to quinones is broad, with a variety of alkyl- and arylboronic acids undergoing efficient cross-coupling. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone. This method has been applied to complex substrates, including a steroid derivative and a farnesyl natural product.