Bis(4-amino-2-chloro-3,5-diethylphenyl)methane
[CAS# 106246-33-7]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anilines
• Name: Bis(4-amino-2-chloro-3,5-diethylphenyl)methane
• Synonyms: 4,4'-Methylenebis(3-chloro-2,6-diethylaniline)
• Molecular Formula: C₂₁H₂₈Cl₂N₂
• Molecular Weight: 379.37
• CAS Registry Number: 106246-33-7
• EC Number: 402-130-7
• SMILES: CCC1=CC(=C(C(=C1N)CC)Cl)CC2=C(C(=C(C(=C2)CC)N)CC)Cl

Properties

• Solubility: 0.001265 mg/L (25 ºC water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.598, Calc.^*
• Melting point: 211.48 ºC
• Boiling Point: 506.4±45.0 ºC (760 mmHg), Calc.^*, 497.60 ºC
• Flash Point: 260.1±28.7 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS09 Warning
• Hazard Statements: H411-H413
• Precautionary Statements: P273-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovory and Applicatios

Bis(4-amino-2-chloro-3,5-diethylphenyl)methane, a symmetrical aromatic diamine compound, is a specialized chemical with the molecular formula C₁₉H₂₆Cl₂N₂. The structure of this compound consists of two phenyl rings, each substituted with chlorine at the second position, amino groups at the fourth position, and ethyl groups at the third and fifth positions, all linked by a central methylene (-CH₂-) bridge. This particular arrangement of functional groups imparts unique chemical properties to the molecule, making it valuable in various industrial applications, particularly in polymer chemistry and material science.

The discovery of Bis(4-amino-2-chloro-3,5-diethylphenyl)methane was part of ongoing research into aromatic amines during the mid-20th century, driven by the demand for high-performance materials, especially polymers. Aromatic diamines like this compound have been widely explored due to their ability to react with diisocyanates to form polyurethanes and polyamides, materials known for their strength, durability, and resistance to harsh environmental conditions. This compound emerged from efforts to synthesize amine derivatives that could contribute to the development of polymers with improved thermal stability, mechanical properties, and resistance to chemical degradation.

One of the most significant applications of Bis(4-amino-2-chloro-3,5-diethylphenyl)methane is in the production of specialty polymers, particularly polyureas and polyimides. Polyureas are formed through the reaction between diamines and isocyanates, resulting in materials with exceptional toughness, chemical resistance, and flexibility. These properties make polyureas ideal for coatings, adhesives, and sealants used in industries such as construction, automotive, and aerospace. Bis(4-amino-2-chloro-3,5-diethylphenyl)methane, with its specific substitution pattern, enhances the performance of these polyurea systems by contributing to their long-term stability and resistance to environmental factors like moisture and temperature extremes.

In polyimide synthesis, aromatic diamines such as Bis(4-amino-2-chloro-3,5-diethylphenyl)methane play a crucial role in creating high-performance polymers known for their excellent heat resistance and mechanical strength. Polyimides are widely used in electronics, aerospace, and automotive applications, where materials are required to withstand high temperatures and maintain their structural integrity. The inclusion of chlorine and ethyl groups on the phenyl rings of this diamine influences the polymer’s flexibility and thermal properties, providing an optimal balance between rigidity and processability.

Another important application of Bis(4-amino-2-chloro-3,5-diethylphenyl)methane is in the production of elastomers. Elastomers, or rubber-like materials, benefit from the incorporation of aromatic diamines in their polymer backbone, which enhances their resistance to oxidative degradation and improves their mechanical properties. The diamine's ability to cross-link with other polymer chains allows for the creation of materials that are more resilient under mechanical stress and less prone to wear and tear. As a result, elastomers made with this compound are employed in applications where durability and flexibility are paramount, such as in automotive parts, gaskets, and seals.

In addition to its role in polymer chemistry, Bis(4-amino-2-chloro-3,5-diethylphenyl)methane has also been studied for its potential in the synthesis of advanced materials with unique properties. Its amine functionality allows it to participate in a variety of reactions, making it a versatile building block in the creation of novel compounds. Research has explored its use in developing thermally stable resins and composites, materials that are of particular interest in industries requiring high-performance materials capable of withstanding extreme conditions.

While Bis(4-amino-2-chloro-3,5-diethylphenyl)methane offers numerous advantages in industrial applications, it is essential to consider the safety and environmental impact associated with its use. Like many aromatic amines, this compound can pose health risks if not handled properly. It may cause skin and respiratory irritation, and prolonged exposure could lead to more severe health effects. As a result, proper safety measures, including the use of protective equipment and adequate ventilation, are necessary when working with this compound in industrial settings. Additionally, disposal of waste materials containing Bis(4-amino-2-chloro-3,5-diethylphenyl)methane must be managed carefully to prevent environmental contamination, as aromatic amines can be persistent in the environment and potentially harmful to aquatic life.

In conclusion, Bis(4-amino-2-chloro-3,5-diethylphenyl)methane is a valuable chemical in the field of polymer and material science. Its discovery and subsequent application in the production of polyureas, polyimides, and elastomers have made it an essential component in the development of high-performance materials. While it presents certain safety challenges, its unique properties continue to make it a critical material in industries where durability, chemical resistance, and thermal stability are crucial.