4871-62-9

Usage

General Description

2,4-Pyrimidinediamine, N,N',6-trimethyl-N,N'-diphenyl- is a chemical compound that is also known as diphenyl-p-phenylenediamine or DPPD. It is commonly used as an antioxidant in rubber and as a stabilizer for gasoline. This chemical is a white to light brown crystalline solid that is insoluble in water and has a melting point of around 155 degrees Celsius. It is known for its ability to prevent the degradation of rubber and other polymer materials caused by heat, oxygen, and ozone, making it an important additive in the production of rubber-based products. Furthermore, it is also used in the production of dyes and pharmaceuticals. However, it is important to handle and store this chemical with caution as it can be harmful if ingested or inhaled.

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 626-48-2 2,4-dihydroxy-6-methylpyrimidine 
• 5424-21-5 2,4-dichloro-6-methylpyrimidine 
• 100-61-8 N-methylaniline 

Relevant academic research and scientific papers

Pyrimidines. 7. A Study of the Chlorination of Pyrimidines with Phosphorus Oxychloride in the Presence of N,N-Dimethylaniline

The chlorination of 6-trifluoromethyluracils by phosphorus oxychloride in the presence of N,N-dimethylaniline was studied and compared with results obtained with 6-methyluracils. 6-Trifluoromethyluracils and its 5-chloro analog afforded moderate yields of the di- and trichloropyrimidines, accompanied by good yields of the 2-N-methylanilino by-products, after a 3-hour reaction time.After 24 hours, the 2-N-methylanilinopyrimidines were the primary or sole products.A small yield of 2,4-bis(N-methylanilino)-6-trifluoromethylpyrimidine was also obtained.The 6-methyluracils afforded high yields of the di- and trichloropyrimidines, after 3 and 24 hours, along with minor amounts of the 2-N-methylanilino by-products.After 48 hours, the proportion of 2,4-dichloro-6-methylpyrimidine decreased, and the 2-N-methylanilino product increased. 2-Chloro-4-methylanilino-6-methylpyrimidine and bis(2-N-methylanilino)-6-methylpyrimidine were also formed in small amounts.The chlorination products from 5-chloro-6-methyluracil remained constant over 188 hours of reaction time. It appears that the Π electron distribution around the ring, as influenced by the substituents, controls the course of the chlorination and by-product formation.Since the amination by a tertiary amine is a type of Hoffmann reaction, the presence of the chlorine in 5 position of the ring adds steric hindrance and thus enhances the regiospecificity of the formation of by-products.