Benzenesulfonic 4-amino-2-

Schwarz, n. slop-padded aniline black. -SI, n. aniline oil. -rot, n. aniline red. -salz, n. aniline salt, -schwarz, n. aniline black, -soifoskure, /. anilinesulfonic acid (amino-benzenesulfonic acid), -tinte,/. aniline ink. -vergiftung, /. aniline poisoning. 

Briliant Blue FCF (E 133, FD C Blue No. 1, Cl Food Blue 2) is a triarylmethane dye disodium 3-[N-ethyl-N-[4-[[4-[N-ethyl-N-(3-sulfonatobenzyl)-amino] phenyl] (2-sulfonatophenyl)methylene]-2,5-cyclohexadiene-l-ylidene]ammoniome-thyl] benzenesulfonate (or disodium (4-(N-ethyl-3-sulfonato-benzylamino) phenyl)-a-(4-N-ethyl-3-sulfonatobenzylamino)cyclohexa-2,5-dienylidene)-toluene-2-sul-... 

Plant Chlorsulfuron is metabolized by plants to hydroxylated, nonphytotoxic compounds including 2-chloro-7V-(((4-methoxy-6-methyl-l,3,5-triazin-2-yl)amino)carbonyl)benzenesulfon-amide (Duke et al., 1991). Devine and Born (1985) and Peterson and Swisher (1985) reported that the uptake of chlorsulfuron in Canada thistle leaves ranged from 23 to 43% after 2 d. The uptake in roots is higher under slightly acidic conditions. Fredrickson and Shea (1986) reported 12% of C-chlorsulfuron was taken up in the roots at soil pH 5.9. 

In 2006, Akiyama and coworkers established an asymmetric Brpnsted acid-catalyzed aza-Diels-Alder reaction (Scheme 36) [59]. Chiral BINOL phosphate (R)-3o (5 mol%, R = 2,4,6- Pr3-CgH2) bearing 2,4,6-triisopropylphenyl groups mediated the cycloaddition of aldimines 94 derived from 2-amino-4-methylphenol with Danishefsky s diene 95 in the presence of 1.2 equivalents of acetic acid. Piperidinones 96 were obtained in good yields (72 to >99%) and enantioselectivi-ties (76-91% ee). While the addition of acetic acid (pK= 4.8) improved both the reactivity and the selectivity, the use of benzenesulfonic acid (pK= -6.5) as an additive increased the yield, but decreased the enantioselectivity. A strong achiral Brpnsted acid apparently competes with chiral phosphoric acid 3o for the activation of imine 94 and catalyzes a nonasymmetric hetero-Diels-Alder reaction. The role of acetic acid remains unclear. 

A second example is the yellow pyrazolone salt, Pigment Yellow 191 [129423-54-7]. It is the calcium salt of diazotized 2-amino-4-chloro-5-methyl-benzenesulfonic acid coupled with 3-methyl-1-[3 —sulfophenyl]-5-pyrazolone and provides a reddish yellow pigment for use in plastics applications. It shows very good heat stability and excellent resistance to nonpolar solvents and commonly used plasticizers (qv). It finds applications in high density polyethylene, polystyrene, and ABS, and shows satisfactory lightfastness. 

Formation of quinuclidine-3-carboxylic acid derivatives (68) from these reactions was conclusive proof of saponification of the ethoxy-carbonyl group at position 2 of the diester (61). A similar reaction takes place with diethyl quinuclidine-2,3-dicarboxylate.100 This is in agreement with the known principle of easier saponification of a- than j8-amino acid esters. Some 3-(j8-acyloxyethyl)-2-diethylaminomethyl-quinuclidines (69, 70)123 on distillation at atmospheric pressure cyclize with loss of ester and formation of a new tricyclic system, quinuclidino[2,3-c]piperidine (72). The same reaction takes place by heating the corresponding amino alcohol (71) with phthalic anhydride in the presence of benzenesulfonic acid.123... 

Methylation of 7-amino-l,2,3-triazolo[4,5-d]pyrimidine (8-azaadenine) (140) with dimethyl sulfate afforded the N-3 and N-9 methylated isomers 141 and 142, respectively, which upon further methylation with methyl iodide or benzenesulfonic acid methyl ester gave 3,7- and l,9-dimethyl-8-azaadeninium salts 144 and 145, respectively. Thermal decomposition of the dimethyl derivatives led to a transmethylation to give 6-methylamino-9-methyl-8-azapurine (143), whose methylation afforded 1- and 7-methyl-6-methylamino-9-methyl-8-azapurinium salts 146 and 147 (80ZOR2204) (Scheme 28). 

Without further drying, the potassium 4-chloro-3,5-dinitro-benzenesulfonate is recrystallized from 600 ml. of boiling water (Note 3). Insoluble material is removed by decantation and filtration of the hot solution. The solution is cooled to 5-10° for 12 hours, and the crystalline potassium salt is collected on a suction filter, pressed as dry as possible, and placed at once in a solution of 400 ml. of concentrated ammonium hydroxide (sp. gr. 0.90) in 400 ml. of water. The solution is boiled for 1 hour under a reflux condenser which has been connected to a gas absorption trap,2 and then is cooled at 5-10° for 12 hours. The orange, crystalline potassium 4-amino-3,5-dinitrobenzenesulfo-nate is filtered with suction and pressed as dry as possible on a 10-cm. Buchner funnel. 

Furfural (18) was oxidized to give the butenolide 19, which on Michael condensation with diethyl ethylmalonate afforded lactone 20. Hydrolysis of 20 yielded the dilactone 21. This was treated with ethanol in the presence of sulfuric acid. The isomer mixture obtained was separated by preparative thin-layer chromatography, yielding 4-ethoxy-3-ethoxycarbonylmethyl-2-ethyl-4-butanolide (22). Elimination of ethanol, with the aid of p-amino-benzenesulfonic acid, gave 2-(3//)-furanone 23 the 2-(5//)-furanone isomer 24 was obtained with the aid of orthophosphoric acid. Both isomeric esters gave the acid 25 after hydrolysis, which on catalytic hydrogenation afforded m-3-carboxymethyl-2-ethyl-4-butanolide 26, identical to homopilopic acid. This synthesis of homopilopic acid differs from earlier syntheses because the less stable cw-2,3-disubstituted butanolide (26) is formed in the last step. 

Pipecolic acid 2-Piperidinecarboxylic acid Sulfanilic acid Benzenesulfonic acid, 4-amino-... 

Eisen HN, Belman S, Carsten ME. The reaction of 2,4-dinitro-benzenesulfonic acid with free amino groups of proteins. J. Am. Chem. Soc. 1953 75 4583-4585. 

Bubnis, W.A. Ofner, C.M., III. The determination of 8-amino group in soluble and poorly soluble proteinaceous materials by a spectrophotometric method using trinitro-benzenesulfonic acid. Anal. Biochem. 1992, 207, 129-133. Liu, W.G. Yao, K.D. Wang, G.C. Li, H.X. Intrinsic fluorescence investigation on the change in conformation of cross-linked gelatin gel during volume phase transition. Polymer 2000, 41, 7589-7592. 

Reductive oxidation of />-nitrotoluene to -aminobenzaldehyde, 31, 6 Reformatsky reaction, 37, 38 Reissert s compound, 38, 58 Reissert reaction, 38, 58 Replacement, benzenesulfonate groups by bromine atoms, 31, 82 bromine, by a thiol group, 30, 35 by fluorine, 36, 40 chlorine, by an amino group, 31,45 by a thiol group, 32, 101 by iodine, 30, 11 by methoxyl, 32, 79 by nitrile, 36, 50 in an imido-chloride group by an anilino group, 31, 48 chlorine and nitro by ethoxyl radicals, 32,68... 

Although sulfonation resembles nitration and halogenation in many respects, there are certain important differences. The two most noticeable of these differences are the reversibility of sulfonation processes and the striking sensitivity of orientation to changes in the reaction temperature. Amino derivatives offer a further complication in that considerable amounts of ortho and para derivatives are often obtained. Thus at low temperatures, aniline gives a mixture of 0, m, and p-amino-benzenesulfonic acid,48 whereas dimethylaniline gives an almost equal... 

Attempts to improve selectivity and sensitivity of spectrophotometric measurements by using new chromogenic reagents, e.g. of 2-(5-nitro-2-pyridylazo)-5-(A -propyl-A-sulfopropylamino)phenol for flow-injection-spectrophotometric determination of trace V in river water [3], Af-butyl-A -(sodium p-amino benzenesulfonate) thiourea to determine Pd in minerals and catalysts [4], benzeneacetaldehyde-4-hydroxy-oxo-aldoxime to determine Co in pharmaceuticals, biological materials and steels [5], 2,6-dichloroarsenazo for the determination of Bi in copper alloys [6], lV-undecyl-A-(sodium p-aminobenzenesulfonate)-thiourea to identify and determine Cu in alloy, liver and wheat [7], dimethoxyhydroxyphenylflurone for the determination of trace amounts of Mo in steel and pure iron [8] and 5-(6-methoxy-2-benzothiazole-azo)-8-aminoquinoline for the detection of Co in drainage sediment and Ni in A1 alloy [9] have recently been reported. 

R = Me) (Lafont and Descotes 1988). The amino glycoside is then obtained by hydrazinolysis. Treatment of protected glycals with benzenesulfon-amide and iodonium dicollidine perchlorate gave compounds 10.49. Again, the corresponding aziridines were not isolated but the expected product of opening... 

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