2-tert-Butyl-5*methylphenol

SYNS BIS(3-tert-BU1TL-4-HYDROXY-6-METHYL-PHENYL) SULFIDE BIS(4-HYDROXY-5-tert-BUTyL-2-METHYLPHENYL) sulfide DISPERSE MB-61 SANTONOX SANTOVC HITE CRYSTALS THIOALKOFEN BM 4 4,4 -THIOBIS(2-tert-BUTYL-5-METHYLPHENOL) 4,4 -THIOBIS(6-tert-BUTYL-3-METHYLPHENOL) 4,4 -THIOBIS(3-METHYL-6-tert-BUTYLPHENOL) l,l -THIOBIS(2-METHYL-4-HYDRO-XY-5-tert-BUTYLBENZENE) USAFB-15 YOSHINOX S... 

Cl 1HI403 2-hydroxy-3-methyl-6-isopropylbenzoic acid 4389-53-1 22.07 1.0913 2 22402 Cl1 HI 60 2-tert-butyl-5-methylphenol 88-60-8 80.00 0.9220 1... 

C11H15N02 m-cumenol methylcarbamate 64-00-6 489.15 42.843 2 22402 C11H160 2-tert-butyl-5-methylphenol 88-60-8 486.71 37.361 2... 

Dioctadecyl 3,5-di-tert-butyl-4-(hydroxybenzyl)phosphonate, 2 == 2,6-Bis(2-octadecyl)-4-methylphenol, 3 = 2,6-Di-tert-butylphenol, 4 = Pentaerythritol tetra-kis[3-[3,5-di-tert-butyl-4-(hydroxyphenyl)Jpropoinate], 5 = 2-tert-Butyl-4,6-dimeth-ylphenol, 6 = 2-tert-Butylphenol, 7 = 2,6-Diisopropylphenol, 8 = 1,3,5-Tris[3,5-di-tert-butyl-4-(hydroxybenzyl)]-2,4,6-trihydroxytriazine, 9 = l,3,5-Trimethyl-2,4,6-tris[3,5-di-tert-butyl-4-(hydroxybenzyl)]benzene, 10 == Methyl 3-[3,5-di-tert-hutyl-4-(hydroxyphenyl)jpropionate, 11 = Monoethyl 3,5-di-tert-butyl-4-(hydroxybenzyl)-vhosphonate, nickel salt, 12 = 2-tert-Butyl-5-methylphenol, 13 = 4,4 -Methylene-bis(2,6-di-tert-butylphenol), 14 = 2-tert-Butyl-6-methylphenol, 15 = Alkylated 2-tert-butyl-5-methylphenol, 16 = 2-tert-Butyl-4-ethylphenol, 17 = Methyl 3-[3-tert-butyl-4-(hydroxyphenyl)]propionate, 18 = 2,4-Di-tert-butylphenol. 

IMINES, CYCLIC] (Vol 14) 2,2y-Thiobis(6-tert-butyl-4-methylphenol) [90-66-4]... 

Commercial appHcation of this type of reaction is used to produce 2,2 -methylenebis(6-/ f2 -butyl-4-methylphenol) (R = tert — butyl = methyl R = H) and 2,2 -ethylidenebis(4,6-di-/ /f-butylphenol) R = R = tert — butyl R = CH ). 

Di-tert-butyl-p-cresol (2,6-di-tert-butyl-4-methylphenol, butylatedhydroxytoluene, BHT) [128-37-0] M 230.4, m 71.5 , pK 12.23. Dissolved in n-hexane at room temperature, then cooled with rapid stirring, to -60°. The ppte was separated, redissolved in hexane, and the process was repeated until the mother liquor was no longer coloured. The final product was stored under N2 at 0° [Blanchard J Am Chem Soc 82 2014 7960]. Also crystd from EtOH, MeOH, benzene, n-hexane, methylcyclohexane or pet ether (b 60-80°), and dried under vacuum. 

Figure 10.9 Cliromatogi ams of foitified coconut oil obtained by using (a) normal-phase HPLC and (b) GPC/noimal-phase HPLC. Peak identification is as follows 1 (a,b), DL-a-toco-pheryl acetate, 2 (b), 2,6-di-tert-butyl-4-methylphenol 2 (a) and 3 (b), retinyl acetate 3 (a) and 4 (b), tocol 4 (a) and 5 (b), ergocalciferol. Reprinted from Analytical Chemistry, 60, J. M. Brown-Thomas et al., Determination of fat-soluble vitamins in oil matrices by multidimensional liigh-peiformance liquid cliromatography , pp. 1929-1933, copyright 1988, with permission from the American Chemical Society.

SCHEME 9.9 Reversible alkylation of deoxynucleotides by a metabolite of 2,6,-di-tert-butyl-4-methylphenol. 

Meier, B. W. Gomez, J. D. Kirichenko, O. V. Thompson, J. A. Mechanistic basis for inflammation and tumor promotion in lungs of 2,6-di-tert-butyl-4-methylphenol-treated mice electrophilic metabolites alkylate and inactivate antioxidant enzymes. Chem. Res. Toxicol. 2007, 20, 199-207. 

Figure III.1 Product sheet of the phenolic antioxidant 2,2 -methylene-bis-(6-tert-butyl-4-methylphenol). After Gijsman [1], Reproduced by permission of P. Gijsman...

BHT (2,6-di-tert-butyl-4-methylphenol), a phenolic antioxidant, on reaction with NO under neutral conditions, results in scavenging of the potentially harmful NO via radical reactions [143]. Sodium phenolate under basic conditions undergoes a Traube-type reaction at the ortho-position to produce a cupferron derivative [144]. When the ortho-positions are sterically blocked and the para-position does not bear a proton, cyclohexadienone diazeniumdiolates may be formed (Scheme 3.12) [145]. 

Analogously, 5-tributylstannylimidazole 29 was easily obtained from the regioselective deprotonation of 1,2-disubstituted imidazole 28 at C(5) followed by treatment with tributyltin chloride [24]. In the presence of 2.6 equivalents of LiCl, the Stille reaction of 29 with aryl triflate 30 afforded the desired 1,2,5-trisubstituted imidazole 31 with 2,6-di-tert-butyl-4-methylphenol (BHT) as a radical scavenger. Reversal of the nucleophile and electrophile of the Stille reaction also provided satisfactory results. For example, the coupling reaction of 5-bromoimidazole 33, derived from imidazole 32 via a regioselective bromination at C(5), and vinylstannane 34 produced adduct 35 [24],... 

Di-tert-butyl-4-methylphenol, production from butylenes, 4 425... 

Gitchell A, Simonaitis R, Heicklen J. 1974. The inhibition of photochemical smog II. Inhibition by hexafluorobenzene, nitrobenzene, naphthalene, and 2,6-tert-butyl-4-methylphenol. J Air Pollut Control Assoc 24 772-775. 

The remarkably high isotope effects found in Reactions 10 and 10a are almost as embarrassing as was our discovery of an isotope effect of about 15 in the reaction with phenols referred to above. [For 2,6-di-tert-butyl-4-methylphenol in oxidizing styrene at 65°C. we obtained an isotope effect kH/kD = 10.6 (11). We have since carefully measured the isotope effect for 2,4,6-tri-ferf-butylphenol under the same conditions and have obtained a value 15. In these cases, hydrogen bonding to the solvent is relatively unimportant (6, 12). Similarly, DaRooge and Mahoney (9) have reported that for the reaction of 2,4,6-tri-tert-butylphenoxy radicals with 4-phenylphenol kH/kD 7.5.] Although... 

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