7033-42-3

Usage

Appearance

Yellow to orange crystalline powder

Solubility

Insoluble in water

Primary use

Photoinitiator in the production of printing inks, coatings, and adhesives

Additional use

Stabilizer in plastics and rubber to prevent degradation caused by UV radiation

Other applications

Synthesis of pharmaceuticals, dyes, and other organic compounds

Safety precautions

May be harmful if ingested, inhaled, or in contact with skin and eyes; should be handled with care

Upstream product

• 80357-53-5 (1,3-dimethyluracilate-C₅)HgCl 
• 65904-27-0 <1,3-Dimethyl-2,4(1H,3H)-dioxopyrimidin-5-yl>mercuric acetate 
• 17237-74-0 (4aR*,4bS*,8aS*,8bR*)-1,3,6,8-tetramethylhexahydrocyclobuta[1,2-d:4,3-d']dipyrimidine-2,4,5,7(3H,6H)-tetraone 
• 17237-74-0 trans,syn-1,1',3,3'-Tetramethyluracil cyclobutadipyrimidine 
• 874-14-6 1,3-dimethyluracil 
• 85199-75-3 1,3-dimethyl-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

C-H trifluoromethylations of 1,3-dimethyluracil and reactivity of the products in C-H arylations

Diverse electrophilic, nucleophilic and radical C-H trifluoromethylations of 1,3-dimethyluracil were systematically studied in order to prepare either 5- or 6-(trifluoromethyl)uracil derivatives. Electrophilic reagents led only to dimeric bis-uracil products, whereas the radical trifluoromethylation by CF 3SO2Na in presence of t-BuOOH gave 1,3-dimethyl-5- (trifluoromethyl)uracil (2) in good yield. The 6-(trifluoromethyl)uracil derivative 3 was only prepared in low yield and in a mixture with 2 by Ir-catalyzed borylation followed by treatment with the Togni's reagent. Attempted Pd-catalyzed C-H arylations of 2 in the presence of Cs 2CO3 gave mixtures of de-trifluoromethylated products, whereas the reaction with 4-iodotoluene in the presence of CsF gave the desired 6-aryl-5-trifluoromethyluracil derivative 8 in moderate yield and the reaction was not general for other aryl halides.

Palladium(II)-catalyzed oxidative homo-coupling of 1,3-dimethyluracil derivatives

A palladium-catalyzed oxidative homo-coupling of 1,3-dimethyluracil was examined. Two types of uracil dimer, C5-C5′ linked dimer and C5-C6′ linked dimer were obtained in variable yields depending on the conditions along with a low yield of C5-C5′ and C6-C

Oxidative cleavage of a cyclobutane pyrimidine dimer by photochemically generated nitrate radicals (no(3)*).

[reaction: see text] Photochemically generated nitrate radicals (NO(3)(*)) cleave the stereoisomeric N,N-dimethyl-substituted uracil cyclobutane dimers 1a-d into the monomeric uracil derivative 2 as the major reaction pathway. A preferred splitting of the syn dimers 1a,b was observed. The reaction is expected to proceed through initial one-electron oxidation with formation of an intermediate cyclobutane radical cation 11. In addition to cycloreversion, competing reaction steps of 11, which lead to the observed byproducts, are suggested.