1,4-Diisopropylbenzene
[CAS# 100-18-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 1,4-Diisopropylbenzene
• Synonyms: p-Diisopropylbenzene
• Molecular Formula: C₁₂H₁₈
• Molecular Weight: 162.27
• CAS Registry Number: 100-18-5
• EC Number: 202-826-9
• SMILES: CC(C)C1=CC=C(C=C1)C(C)C

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.857 g/mL (Expl.)
• Melting point: -17 ºC (Expl.)
• Index of Refraction: 1.488, Calc.^*, 1.489 (Expl.)
• Boiling Point: 210.5 ºC (760 mmHg), Calc.^*, 210 ºC (Expl.)

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Hazard Statements: H315-H335-H336-H361-H400-H410-H413
• Precautionary Statements: P203-P261-P264-P271-P273-P280-P302+P352-P304+P340-P318-P319-P321-P332+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - single exposure	STOT SE	3	H335
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 3082

Discovory and Applicatios

1,4-Diisopropylbenzene is an organic compound characterized by the formula C₁₂H₁₆, containing two isopropyl groups attached to a benzene ring at the 1 and 4 positions. It is a colorless liquid at room temperature and is primarily synthesized through the Friedel–Crafts alkylation reaction. This chemical is significant in various industrial applications due to its unique chemical properties.

The compound was first synthesized through the reaction of isopropyl chloride with benzene in the presence of a Lewis acid catalyst, such as aluminum chloride (AlCl₃). This process results in the substitution of the hydrogen atoms on the benzene ring with isopropyl groups at the para positions. Over time, 1,4-diisopropylbenzene has been identified as a crucial intermediate for the production of several other chemicals.

The most notable application of 1,4-diisopropylbenzene is in the production of specialty chemicals. It is used as a building block for a variety of organic compounds, including pharmaceuticals and agrochemicals. It plays a role as a solvent in some industrial processes due to its relatively low volatility and stability. In addition, it is used in the formulation of high-performance polymers and resins, where its presence helps modify the physical properties of the materials. Its chemical structure lends itself to being a useful component in applications that require modifications in the flexibility and thermal stability of materials.

In addition to its use as an intermediate, 1,4-diisopropylbenzene is a precursor in the production of plasticizers. These are substances that are added to polymers to enhance their flexibility and workability. The compound’s ability to alter the properties of synthetic materials makes it valuable in the production of plastics and related materials, which are essential in industries such as automotive, electronics, and packaging.

Beyond its industrial uses, 1,4-diisopropylbenzene is also studied in scientific research. It serves as a model compound for studying the alkylation reactions of aromatic hydrocarbons. Researchers focus on its reactivity in order to understand how similar reactions might occur with other alkyl groups and aromatic compounds. This information is essential for developing new synthetic routes to a wide array of organic molecules.

In conclusion, 1,4-diisopropylbenzene plays an essential role in industrial chemistry and research. Its synthesis, which is primarily based on Friedel–Crafts alkylation, has been well documented, and its applications range from use in the production of specialty chemicals and polymers to serving as a precursor for plasticizers. The compound continues to be an important building block in the chemical industry and is a subject of ongoing research in the field of organic synthesis.

References

2016. Structural characterization and prediction of Kovats retention indices (RI) for alkylbenzene compounds. Journal of Structural Chemistry, 57(8).
DOI: 10.1134/s0022476616080060

2019. Refining of Diesel and Ship Fuels by Extraction and Combined Methods. Part 2. Use of Organic Solvents as Extractants. Russian Journal of Applied Chemistry, 92(5).
DOI: 10.1134/s107042721905001x

2023. Synthesis of valuable benzenoid aromatics from bioderived feedstock. Nature Sustainability, 6(8).
DOI: 10.1038/s41893-023-01190-w