Triazines 2,4,6-trichloro

Cyanuric chloride (2,4,6-trichloro-sym-l,3,5-triazine chloro-triazine trichloro-cyanidine). This is widely available. A high-purity (99%) compound should be used. It is a very reactive compound, and must be stored at 2-8°C in an anhydrous environment. It should be recrystallized in petroleum ether (see Note 1). Hazards Poison, lachrymator, and irritant to eyes, skin and respiratory system. May be harmful if swallowed. Toxicity data LD50 485 mg/kg oral, rat. Should be handled in a fume hood with safety glasses and gloves, and treated as a possible cancer hazard. 

G.J. Kearley, J. Tomkinson, A. Navarro, J.J. L6pez-Gonzdlez, M. Femandez-Gomez (1997). Chem. Phys., 216, 323-335. Symmetrised quantum-mechanical force-fields and INS spectra s-triazine, trichloro-s-triazine and pyrazine. 

Trichloro-s-triazine Trichloro-s-triazine sym-Trichlorotriazine Tricyanogen chloride... 

Trichlorotriazine 2,4,6-Trichlorotriazine 2,4,6-Trichloro-1,3,5-triazine 2,4,6-Trichloro-s-triazine Trichloro-s-triazine sym-Trichlorotriazine. See Cyanuric chloride... 

Trifluoro-l5355-Triazine. Cyanuric fluoride can be produced from 2,4,6-trichloro-j -l,3,5-triaziae [108-77-0] (cyanuric... 

Oligomeric hindered amine light stabilizers are effective thermal antioxidants for polypropylene. Thus 0.1% of A[,Af-bis(2,2,6,6-tetramethyl-4-piperadinyl)-l,6-hexanediamine polymer, with 2,4,6-trichloro-l,3,5-triazine and 2,4,4-trimethyl-2-pentaneainine [70624-18-9] (35) (Fig. 5), protects polypropylene multifilaments against oxidation when exposed at 120°C in a forced-air oven (22) for 47 days. 3,5-Di-/ l -butyl-4-hydroxytoluene [128-37-0] (0.1%) affords protection for only 14 days. 

Organic Derivatives. Although numerous mono-, di-, and trisubstituted organic derivatives of cyanuric and isocyanuric acids appear in the hterature, many are not accessible via cyanuric acid. Cyanuric chloride 2,4,6-trichloro-j -triazine [108-77-0], is generally employed as the intermediate to most cyanurates. Trisubstituted isocyanurates can also be produced by trimerization of either aUphatic or aromatic isocyanates with appropriate catalysts (46) (see Isocyanates, organic). Alkylation of CA generally produces trisubstituted isocyanurates even when a deUberate attempt is made to produce mono- or disubstituted derivatives. There are exceptions, as in the production of mono-2-aminoethyl isocyanurate [18503-66-7] in nearly quantitative yield by reaction of CA and azitidine in DMF (47). 

Cyanuric chloride (TCT, 2,4,6-trichloro-l,3,5-triazine) [108-77-0] M 184.4, m 146-149 , 154 , h 190 . Crystd from CCI4 or pet ether (b 90-100°), and dried under vacuum. Recrystd twice from anhydrous benzene immediately before use [Abuchowski et al.J Biol Chem 252 3582 1977]. 

Chemical Designations - Synonyms Trichloroiminoisocyanuris acid Trichloroisocyanuric acid Trichloro-s-Triazine-2,4,6-(lH,3H,5H)-trion Trichlorotriazinetrion 1,3,5- Trichloro- 2,4,6-trioxo-1,3,5-triazine Chemical Formula Cl3(NCO)3. 

Direct bromination readily yields the 6-bromo derivative (111), just as with uracil. Analogous chlorination and iodination requires the presence of alkalies and even then proceeds in low yield. The 6-chloro derivative (113) was also obtained by partial hydrolysis of the postulated 3,5,6-trichloro-l,2,4-triazine (e.g.. Section II,B,6). The 6-bromo derivative (5-bromo-6-azauracil) served as the starting substance for several other derivatives. It was converted to the amino derivative (114) by ammonium acetate which, by means of sodium nitrite in hydrochloric acid, yielded a mixture of 6-chloro and 6-hydroxy derivatives. A modified Schiemann reaction was not suitable for preparing the 6-fluoro derivative. The 6-hydroxy derivative (115) (an isomer of cyanuric acid and the most acidic substance of this group, pKa — 2.95) was more conveniently prepared by alkaline hydrolysis of the 6-amino derivative. Further the bromo derivative was reacted with ethanolamine to prepare the 6-(2-hydroxyethyl) derivative however, this could not be converted to the corresponding 2-chloroethyl derivative. Similarly, the dimethylamino, morpholino, and hydrazino derivatives were prepared from the 6-bromo com-pound. ... 

On reaction with aged phosphoroxychloride, 6-azauracil formed 3,5-dichlorotriazine (117) in only a 10% yield. " A somewhat higher yield (30%) was obtained from the reaction of 6-bromodioxotriazine which gave 3,5,6-trichloro-l,2,4-triazine. Similar reactions take place much more readily with uracil and in better yield. " Thus,... 

Trichloro-l,2,4-triazine was reacted with menthanol and subsequently crystallized from w ater to yield 5-chloro-6-azauracil. A chloro-dimethoxy derivative appears to be an intermediate product, this being further cleaved by hydrogen chloride. No 2,4-dimethoxy derivatives have been prepared so far. 

The high reactivity of trichloro-s-triazine and tetrachloropyrimi-dine, the ease of replacement of the first chlorine atom from these compounds with several types of nucleophiles (amines, alcohols, etc.) and, finally, the important role of these reactions in dye chemistry have stimulated many investigations dealing with substituents of the general types RZ and R2Z, where Z is an electron-donor atom or group (NH, 0, S, N). 

The diazomethyl group in 165, formed from 2,4,6-trichloro-s-triazine and diazomethane, deactivates (relative to chloro) the remaining chloro groups towards diazomethane, ammonia, and methoxide ion. 

The highly activated 2,4,6-trichloro-s-triazine with excess amines at... 

Substituents in the 6-position (cf. 267) show appreciable reactivity. 6-Bromo-as-triazine-3,5(2j, 4j )-dione (316) undergoes 6-substitution with secondary amines or hydrazine, with mercaptide anions or thiourea (78°, 16 hr), with molten ammonium acetate (170°, 24 hr, 53% yield), and with chloride ion during phosphorous oxychloride treatment to form 3,5,6-trichloro-as-triazine. The latter was characterized as the chloro analog of 316 by treatment with methanol (20°, heat evolution) and hydrolysis (neutral or acid) to the dioxo compound. The mercapto substituent in 6-mercapto-as-triazine-3,5(2iI,4if)-dione is displaced by secondary... 

Dichloro-s-triazine and its 6-alkyl analogs are as easily hydrolyzed by water as trichloro-s-triazine and, on suspension in aqueous ammonia (25°, 16 hr), the first is diaminated in good yield. 2,4-Bistrichloromethyl-6-methyl- and -6-phenyl-s-triazines (321) require a special procedure for mono-alkoxylation (0-20°, 16 hr, alcoholic triethylamine) disubstitution occurs at reflux temperature (8 hr). Aqueous triethylamine (100°, 3 hr) causes complete hydroxy-lation of 2,4,6-tris-trichloromethyl-s-triazine which can be mono-substituted with ammonia, methylamine, or phenoxide ion at 20°. 

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