1,2-Diisopropylbenzene
[CAS# 25321-09-9]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Aromatic hydrocarbon
• Name: 1,2-Diisopropylbenzene
• Molecular Formula: C₁₂H₁₈
• Molecular Weight: 162.27
• CAS Registry Number: 25321-09-9
• EC Number: 246-835-6
• SMILES: CC(C)C1=CC=CC=C1C(C)C

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.488, Calc.^*
• Boiling Point: 204.0 ºC (760 mmHg), Calc.^*
• Flash Point: 69.0±7.1 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Hazard Statements: H302-H319-H372-H410
• Precautionary Statements: P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin irritation	Skin Irrit.	2	H315
Aspiration hazard	Asp. Tox.	1	H304
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - single exposure	STOT SE	3	H336

• Transport Information: UN 3082

Discovory and Applicatios

1,2-Diisopropylbenzene, also known as ortho-diisopropylbenzene, is an aromatic hydrocarbon with the molecular formula C12H18. It consists of a benzene ring substituted with two isopropyl groups in the 1 and 2 positions. This compound is one of three positional isomers of diisopropylbenzene, the others being the meta and para isomers. It appears as a colorless liquid with a characteristic aromatic odor and is hydrophobic in nature.

The synthesis of 1,2-diisopropylbenzene typically involves the alkylation of benzene with propylene in the presence of a Lewis acid catalyst, such as aluminum chloride. Controlled conditions and catalyst selection can influence the positional isomer distribution, although mixtures of isomers are often produced. The ortho isomer can be separated through fractional distillation or recrystallization techniques when needed for specific applications.

1,2-Diisopropylbenzene has been employed primarily as an intermediate in organic synthesis. One of its notable uses is as a precursor in the production of dihydroxybenzene derivatives through hydroperoxidation and subsequent cleavage reactions. These processes are analogous to the cumene process used in phenol production. In this context, 1,2-diisopropylbenzene can undergo oxidation to yield dihydroxy aromatic compounds such as catechol or its alkylated analogs.

Additionally, 1,2-diisopropylbenzene and related dialkylbenzenes serve as solvent components and as additives in certain lubricant and fuel formulations. Their chemical stability, hydrophobicity, and relatively low reactivity make them suitable for use in formulations requiring aromatic content with branching for improved solubility and flow properties.

In the field of materials chemistry, 1,2-diisopropylbenzene has also been studied for its role in the synthesis of polyaromatic hydrocarbons and other complex aromatic systems, particularly when substituted derivatives are required for further transformations.

Safety considerations include its classification as a flammable liquid, with typical precautions related to storage and handling of volatile aromatic hydrocarbons. It should be used in well-ventilated environments with appropriate personal protective equipment.

Overall, 1,2-diisopropylbenzene is a well-established aromatic compound used in synthesis and industrial formulations, valued for its branched structure and chemical stability.

References

2019. Benzene Alkylation with Propylene in the Presence of Nanocrystalline Zeolites BEA with Different Compositions. Petroleum Chemistry, 59(12).
DOI: 10.1134/s0965544119120028

2019. Optimization of Parametric Model of Cumene Reactor Using Loop Shaping Methodology and Dynamic Modeling of Reactor. Intelligent Computing, Information and Control Systems.
DOI: 10.1007/978-3-030-30465-2_23

2024. Current progress in the synthesis of zeolite crystals at low temperatures and their catalytic applications. Journal of Nanoparticle Research, 26(4).
DOI: 10.1007/s11051-024-05976-7