Phenyl-l,3,5-triazine

Other amino resins besides MF resins are used to a lesser degree in coatings. Urea—formaldehyde resins are used in some coatings for wood furniture because these resins cross-link at lower temperatures than MF resins and the higher water resistance and exterior durabiUty that can be obtained using MF resins are not needed. Ethers of formaldehyde derivatives of 6-phenyl-l,3,5-triazine-2,4-diamine [91-76-9] (benzoguanamine resins) give... 

Scheme 6.266 Synthesis of 4,6-diamino-2,2-dimethyl-l,2-dihydro-l-phenyl-l, 3,5-triazines.

Phenylguanamine (2,4-diamino-6-phenyl-l,3,5-triazine) is synthesized from benzonitrile and dicyanamide ... 

The stronger stabilizing effect of a y-aza relative to an a-aza atom is confirmed by the behavior of pyridazine and pyrimidine, which preferably form adducts 29 and 30, respectively. Phenyl substituents discourage ipso attack by NH2", as shown by the observation that in the reactions with 4,6-diphenyIpyrimidine, 2-phenyl-l,3,5-triazine, or 2,4-diphenyl-l,3,5-triazine only CH adducts are detected. However, indirect evidence for adducts resulting from attack at CPh positions is provided by a study of the reaction products from diphenyltriazine and related substrates, unequivocally showing that such adducts are transiently formed along an SN (ANRORC) pathway. 

Phenyl-l,3,5-triazine has fewer sterically hindered positions of attack, and therefore can undergo amination by an Sjv(ANRORC) process. Indeed, Simig and van der Plas investigated the reaction by 1H NMR and showed that it does occur partially (ca. 55%) by this mechanism (76RTC125). 

Like acetonitrile, benzonitrile is a powerful solvent fnr many inorganic and organic materials including some polymers. It can be converted to a large number and variety of derivatives by simple syntheses e.g.. by hydrolysis, it can be converted to either benzoic acid nr benzamicle. The most important reaction is with dicyandiamide to produce 2,4-diamino-6-phenyl-l,3,5-triazine (benzogunnamine) ... 

Chemical Name N-Phenyl-l,3,5-triazine-2,4-diamine monohydrochloride Common Name Amanozine, Amenozine Structural Formula ... 

This explains the formation of various products like benzonitrile, 3-phenyl-l,2,4-thiadiazole 103, 2-phenyl-l,3,5 triazine 105a/b, and diphenyl 1,3,5-triazine 104a/b in the photolysis of 5-phenyl-l,2,4-thiadiazole 97. 

The interaction of perfluoro-5-azanon-4-ene with amidines and 2-amino-benzimidazole occurs with formation of a six-membered heterocycle, giving 2,4-bis(heptafluoropropyl)-6-phenyl-[l,3,5]triazine, 2,4-bis(hep-tafhioropropyl)-6-methyl-[l,3,5]triazine, and a tricyclic compound—2,4-bis(heptafhioropropyl)benz-[4,5]imidazo[l,2-tf][l,3,5]triazine (01IZY457). 

The ANRORC mechanism was first observed upon amination of phenyl-1,3,5-triazine (26) with potassium amide in liquid ammonia (76RTC125). When 26 was treated with excess potassium amide in liquid ammonia at -33°C for 40 hr, a low yield (9%) of 4-amino-2-phenyl-l,3,5-triazine (27)... 

Nitrophenyl)-6-phenyl-l,3,5-triazin-2-aiiiine (14, R1 = 4-02NC6H4 R1 = Ph) Typical Procedure 364... 

Aza-l-chloro-l,3-bis(dimethylamino)-3-phenylpropenylium perchlorate (9) reacts with several amidines to yield the corresponding JV,jV-dimethyl-4-phenyl-l,3,5-triazin-2-amines 10 in 20 to 90% yield.415... 

Amino-6-phenyl-l,3,5-triazin-2-ol (2, R = Ph) from Acyldicyanodiamides 1 Typical Procedure 444,4,45... 

When 2-phenyl-l,3,5-triazine (8) is aminated with potassium amide in liquid ammonia at - 33 C a very slow Chichibabin reaction occurs, partly via the Sn(ANRORC) mechanism and partly via the SNAE process (ratio ca. 55 45). H NMR and l5N-labelling studies have demonstrated that in solution an equilibrium exists between the starting triazine, amine adducts, open-chain amidines and triazine product 9.53... 

Acylation occurs at N-1 of 6-(dimethylamino)-4-phenyl-l,3,5-triazine-2(l/ )-thione as shown in Scheme 5 <89AKZ407>. 

Tokui T, Brozovich, F, Ando S, Ikebe M (1996) Enhancement of smooth muscle contraction with protein phosphatase inhibitor 1 Activation of inhibitor 1 by cGMP dependent protein kinase. Biochem Biophys Res Commun 220 777-783 Tdrbk K, Trentham DR (1994) Mechanism of 2-chloro-(epsilon-amino-Lys75)-[6-[4-(Nd -diethylamino)phenyl]-l,3,5-triazin-4-yl]calmodulin interactions with smooth muscle myosin light chain kinase and derived peptides. Biochemistry 33 12807-12820... 

Various copolymers of 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(2-hydroxy-3-[2-methylpropenoyloxy])propoxy-phenyl]-l,3,5-triazine, with styrene, methyl methacrylate, and methacrylic acid have been synthesized by radical polymerization. Their absorption spectra in the long-wavelength UV region appear unchanged compared to those of the monomeric UV absorbers, indicating that the stabilizer chromophore remains unimpaired in the course of the polymerization. 

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