N,N-Diisopropylaniline
[CAS# 4107-98-6]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: N,N-Diisopropylaniline
• Molecular Formula: C₁₂H₁₉N
• Molecular Weight: 177.29
• CAS Registry Number: 4107-98-6
• EC Number: 625-530-5
• SMILES: CC(C)N(C1=CC=CC=C1)C(C)C

Properties

• Density: 0.91
• Boiling point: 95-96 °C (11 mmHg)
• Refractive index: 1.519
• Flash point: 84 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

N,N-Diisopropylaniline, often abbreviated as DIPN, is an organic compound characterized by its distinct chemical structure, which consists of an aniline core with two isopropyl groups attached to the nitrogen atom. This compound was first synthesized in the early 20th century as part of a broader investigation into substituted anilines and their potential applications in the chemical industry. Researchers recognized the importance of modifying the aniline structure to enhance its chemical properties and broaden its utility.

The discovery of N,N-diisopropylaniline was driven by the need for effective intermediates in the synthesis of dyes, pharmaceuticals, and other organic compounds. Its unique structure imparts specific characteristics, such as increased steric hindrance and reduced basicity compared to its parent compound, aniline. These properties make DIPN a valuable building block in the synthesis of various chemical products, particularly in the dye and pigment industries.

One of the primary applications of N,N-diisopropylaniline is as a catalyst and intermediate in the production of polyurethane foams. In this context, DIPN acts as a chain extender or crosslinking agent, facilitating the polymerization process. The steric properties of the isopropyl groups contribute to the formation of flexible and durable polyurethane materials, which are widely used in furniture, automotive interiors, and insulation applications.

In addition to its role in polyurethane production, N,N-diisopropylaniline is employed in the synthesis of specialty chemicals and agrochemicals. Its unique structure allows for the introduction of further functional groups, enabling the development of more complex molecules. This versatility has made DIPN an important compound in the research and development of new chemical entities for various applications, including pharmaceuticals and agricultural products.

The compound's properties also lend themselves to its use as a solvent in various chemical reactions. Its relatively low toxicity compared to other organic solvents makes it an attractive alternative for specific applications, particularly in laboratory settings. Furthermore, DIPN is used in the production of rubber additives and stabilizers, where it contributes to the performance and longevity of rubber products.

Despite its numerous applications, safety considerations surrounding the use of N,N-diisopropylaniline are essential. Like many organic compounds, it can pose health risks if not handled properly. Manufacturers and end-users must adhere to safety guidelines and regulations to ensure safe handling and usage. Proper ventilation, protective equipment, and adherence to material safety data sheets are crucial in mitigating potential risks associated with its use.

In summary, N,N-Diisopropylaniline is a versatile chemical compound with significant applications in the production of polyurethanes, specialty chemicals, and as a solvent. Its unique structure and properties make it an essential building block in the chemical industry, contributing to the development of various products used in everyday life. As industries continue to seek sustainable and efficient solutions for their challenges, the importance of DIPN in enhancing product performance and developing new materials is expected to grow.

References

2021. N-Arylation of Nitrogen Heterocycles. Science of Synthesis.
URL: SD-236-00178

2020. Simple and Strong Dative Attachment of α-Diimine Nickel (II) Catalysts on Supports for Ethylene Polymerization with Controlled Morphology. Catalysis Letters, 150(2).
DOI: 10.1007/s10562-020-03116-z