93669-69-3

Basic information

• Product Name: 2,4-Pyrimidinediamine, 5-chloro-N,N',6-trimethyl-N,N'-diphenyl-
• CAS NO: 93669-69-3
• Molecular Formula: C19H19ClN4
• Molecular Weight: 338.84
• Mol File: 93669-69-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,4-Pyrimidinediamine, 5-chloro-N,N',6-trimethyl-N,N'-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pyrimidinediamine, 5-chloro-N,N',6-trimethyl-N,N'-diphenyl-(93669-69-3)
• EPA Substance Registry System: 2,4-Pyrimidinediamine, 5-chloro-N,N',6-trimethyl-N,N'-diphenyl-(93669-69-3)

Safety Data

• Hazardous Substances Data: 93669-69-3(Hazardous Substances Data)

Upstream product

• 6554-69-4 6-Methyl-2,4,5-trichloropyrimidine 
• 100-61-8 N-methylaniline 
• 16018-87-4 5-Chloro-6-methyluracil 

Relevant articles and documents

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.