Sulfonic acids, 2-amino

Naphthol-7-sulfonic acid, 2-amino-6-(2-hydroxy-6-nitro-... 

Thiazoles, vinyl-radical polymerization, 6, 278 Thiazole-5-sulfonic acid, 2-amino-synthesis, 6, 255-256 Thiazole-2-sulfonic acids reactions, 5, 104 6, 291 Thiazole-5-sulfonic acids synthesis, 6, 255 Thiazole-5-thione, 2-phenyl-tautomerism, 6, 249 Thiazolethiones reactivity, 6, 250 Thi azole-2-thiones reactions, 5, 102 tautomerism, 5, 367 Thiazolidine, 2-alkyl-occurrence, 6, 327 Thiazolidine, 2-arylimino-X-ray analysis, 6, 238 Thiazolidine, 4-imino-mesoionic didehydro derivative nomenclature, 1, 34 nomenclature, 1, 34... 

AI3-28529 2-Amino-5-chloro-4-methylbenzenesulf-onic acid 3-Amino-6-chlorotoluene-4-sulfonic acid 5-Amino-2-chlorotoluene-4-sulphonic xid Benzene-sulfonic acid, 2-amino-5-chlotxj-4-methyl- ... 

AI3-18307 Aminoethanesulfonic acid 2-Aminoethane-sulfonic acid p-Aminoethylsulfonic acid 2-Aminoethyl-sulfonic acid CCRIS 4721 EINECS 203-483-8 Ethane-sulfonic acid, 2-amino- FEMA No. 3813 NCI-C60606 NSC 32428 0-Due 2-Sulfoethylamine Tauphon Taurina Taurine L-Taurine Taurinum. Used in biochemical research, pharmaceuticals, wetting agents. Crystals mp = 328 (dec) very soluble in H2O (6.5 g/100 ml), insoluble in organic solvents, Chemisphere Lancaster Synthesis Co. Mitsui Toatsu Penta Mfg. Tanabe U.S.A. Inc. 

Amino-1-phenol-4-sulfonic acid. See2-Aminophenol-4-sulfonic acid 2-Aminophenol-4-sulfonic acid CAS 98-37-3 EINECS/ELINCS 202-662-8 Synonyms 3-Amino-4-hydroxy benzenesulfonic acid 3-Amino-4-hydroxy sulfonic acid 2-Amino-1-phenol-4-sulfonic acid o-Aminophenyl-p-sulfonic acid Empirical C6H7NO4S Formula C6H3OHNH2SO3H Properties Brn. rhombic cryst. or bik. powd. very... 

In these compounds the following substituents can be present alkyl,alkenyl,aryl, halogen,sulfonic acid, amino, hydroxyalkyl, acyl, and carboxyl. The cleavages of 5,5 - (109) and 3,5 -diisoxazolyl (111) proceed similarly both isoxazole rings are cleaved in the former (109—> 110). ... 

Amino-4-(3-(b-hydroxyethylsulfonyl-phenylamino))anthraquinone-2-sulfonic acid [39582-26-8... 

Amino-3-hydroxy-7-nitro-l-naphthalene-sulfonic acid [6259-63-8]... 

Esters. Most acryhc acid is used in the form of its methyl, ethyl, and butyl esters. Specialty monomeric esters with a hydroxyl, amino, or other functional group are used to provide adhesion, latent cross-linking capabihty, or different solubihty characteristics. The principal routes to esters are direct esterification with alcohols in the presence of a strong acid catalyst such as sulfuric acid, a soluble sulfonic acid, or sulfonic acid resins addition to alkylene oxides to give hydroxyalkyl acryhc esters and addition to the double bond of olefins in the presence of strong acid catalyst (19,20) to give ethyl or secondary alkyl acrylates. 

Stilben-4-yl)naphthotriazoles (2) are prepared by diazotization of 4-amino-stilbene-2-sulfonic acid or 4-amino-2-cyano-4 -chlorostilbene, coupling with an ortho-coupling naphthylamine derivative, and finally, oxidation to the triazole. 

Ethyleneimine reacts rapidly with sulfurous acid to give taurine [107-35-7] in high yield, a reaction of importance not only for the preparation of this amino sulfonic acid but also for the decontamination of ethyleneimine solutions (130). 

Phthalocyanine sulfonic acids, which can be used as direct cotton dyes (1), are obtained by heating the metal phthalocyanines in oleum. One to four sulfo groups can be introduced in the 4-position by varying concentration, temperature, and reaction time (103). Sulfonyl chlorides, which are important intermediates, can be prepared from chlorosulfonic acid and phthalocyanines (104). The positions of the sulfonyl chloride groups are the same as those of the sulfonic acids (103). Other derivatives, eg, chlormethylphthalocyanines (105—107), / /f-butyl (108—111), amino (112), ethers (109,110,113—116), thioethers (117,118), carboxyl acids (119—122), esters (123), cyanides (112,124—127), and nitrocompounds (126), can be synthesized. 

Pigment Red 177 [4051-63-2] 65300 anthraquinone bimolecular debromination of l-amino-4-bromoanthraquiQone-2-sulfonic acid, foUowed by desulfonation... 

Sodium Bisulfite. Sodium bisulfite [7631-90-5] NaHSO, is occasionally used to perform simultaneous reduction of a nitro group to an amine and the addition of a sulfonic acid group. For example, 4-amino-3-hydroxyl-l-naphthalenesulfonic acid [116-63-2] C qH NO S, is manufactured from 2-naphthol in a process which uses sodium bisulfite (59). The process involves nitrosation of 2-naphthol in aqueous medium, followed by addition of sodium bisulfite and acidification with sulfuric acid. 

The history of the discovery of amino acids is closely related to advances ia analytical methods. Initially, quantitative and qualitative analysis depended exclusively upon crystallization from proteia hydrolysates. The quantitative precipitation of several basic amino acids including phosphotungstates, the separation of amino acid esters by vacuum distillation, and precipitation by sulfonic acid derivatives were developed successively duriag the last century. 

Anthraquinone can be sulfonated, nitrated, or halogenated. Sulfonation is of the greatest technical importance because the sulfonic acid group can be readily replaced by an amino or chloro group. Sulfonation with 20—25% oleum at a temperature of 130—135°C produces predominandy anthraquinone-2-sulfonic acid [84-48-0]. By the use of a stronger oleum, disulfonic acids are produced. The second sulfonic acid substituent never enters the same ring a mixture of 2,6- and 2,7-disulfonic acids is formed (Wayne-Armstrong rule). In order to sulfonate in the 1-, 1,5-, or 1,8-positions, mercury or one of its salts must be used as a catalyst. 

Taufine [107-35-7] (2-aminoethanesulfonic acid), is the only known naturally occurring sulfonic acid. The material is an essential amino acid for cats and is used extensively by Ralston Putina Company as a food supplement ia cat food manufacture. Approximately 5,000—6,000 t of tautine (synthetic and natural) were produced ia 1993 50% for pet food manufacture, 50% ia pharmaceutical appHcations (114). 

Technologically, the most important examples of such couplers are 1-naphthylamine, 1-naphthol, and sulfonic acid derivatives of 1-naphthol (Fig. 2). Of great importance in the dyestuff industry are derivatives of l-naphthol-3-sulfonic acid, such as H-acid (8-amino-l-naphthol-3,6-disulfonic acid [90-20-0])... 

J-acid (6-amino-l-naphthol-3-sulfonic acid [87-02-5]) (16), and gamma acid (7-amino-1-naphtho1-3-su1fonic acid [90-51-7]) (17). 

Diazophenols, ie, o-hydroxyaryldiazonium salts, couple to 1-naphthol in weaMy basic solution primarily in the para position, but as the hydroxyl ion concentration is increased, formation of the ortho isomer is favored and is frequentiy the sole product. Pyridine and pyridine derivatives, urea, and acetate, etc, used as buffers can also catalyze azo coupling reactions (28). l-amino-2-naphthol-4-sulfonic acid [116-63-2] (1,2,4-acid) and 1-naphthol yield the important Eriochrome Black A [3564-14-5] (18a, R = H) (Cl Mordant Black 3 Cl 14640) which is reportedly (20) a mixture of ortho and para isomers. 

Fig. 5. Direct red dyes, (a) Direct Red 81 described ia text (68) (b) Direct Red 2 (o-toLidiae coupled to two moles of naphthionic acid) (69) (c) Direct Red 23 (aniline coupled to 6,6 -ureylenebis-l-naplitliol-3-sulfonic acid with a second coupling with j aminoacetanilide) (70) and Direct Red 80 (2 mol 6-amino-3,4 -azobenzenedisulfonic acid coupled twice to 6,6 -ureylenebis-l-naphthol-3-sulfonic acid) (73). Direct Red 24 (4-aniino-y -toluenesulfonic acid coupled under acidic conditions to 6,6 -ureylenebis-l-naphthol-3-sulfonic acid followed by an alkaline coupling of o-anisidine) (71) (d) Direct Red 72 (Broenner s acid, ie, 6-artiino-2-naphthalenesulfonic acid coupled under acidic conditions to 6,6 -ureylenebis-l-naphthol-3-sulfonic acid followed by an...

The ring-chlorinated derivatives of toluene form a group of stable, industrially important compounds. Many chlorotoluene isomers can be prepared by direct chlorination. Other chlorotoluenes are prepared by indirect routes involving the replacement of amino, hydroxyl, chlorosulfonyl, and nitro groups by chlorine and the use of substituents, such as nitro, amino, and sulfonic acid, to orient substitution followed by their removal from the ring. 

In the anthraquinone series, apart from the special case of the amination of leucoquinizarin, sulfonic acid and nitro are the preferred leaving groups. 1-Aminoanthraquinone is manufactured from anthraquinone-l-sulfonic acid or 1-nitroanthraquinone, and 2-amino anthraquinone (betamine) from anthraquinone-2-sulfonic acid. 

Efforts to raise the alpha-selectivity have been made. Thus nitration of anthraquinone using nitrogen dioxide and ozone has been reported (17). l-Amino-4-bromoanthraquinone-2-sulfonic acid (bromamine acid) [116-81 -4] (8) is the most important intermediate for manufacturing reactive and acid dyes. Bromamine acid is manufactured from l-aminoanthraquinone-2-sulfonic acid [83-62-5] (19) by bromination in aqueous medium (18—20), or in concentrated sulfuric acid (21). l-Aminoanthraquinone-2-sulfonic acid is prepared from l-aminoanthraquinone by sulfonation in an inert, high boiling point organic solvent (22), or in oleum with sodium sulfate (23). 

In the first case (22), almost stoichiometric amounts of sulfuric acid or chlorosulfonic acid are used. The amine sulfate or the amine chlorosulfate is, first, formed and heated to about 180 or 130°C, respectively, to rearrange the salt. The introduction of the sulfonic acid group occurs only in the ortho position, and an almost quantitative amount of l-aminoanthraquinone-2-sulfonic acid is obtained. On the other hand, the use of oleum (23) requires a large excess of SO to complete the reaction, and inevitably produces over-sulfonated compound such as l-amino-anthraquinone-2,4-disulfonic acid. Addition of sodium sulfate reduces the byproduct to a certain extent. Improved processes have been proposed to make the isolation of the intermediate (19) uimecessary (24,25). 

The main by-products of the Ullmaim condensation are l-aniinoanthraquinone-2-sulfonic acid and l-amino-4-hydroxyanthraquinone-2-sulfonic acid. The choice of copper catalyst affects the selectivity of these by-products. Generally, metal copper powder or copper(I) salt catalyst has a greater reactivity than copper(Il) salts. However, they are likely to yield the reduced product (l-aniinoanthraquinone-2-sulfonic acid). The reaction mechanism has not been estabUshed. It is very difficult to clarify which oxidation state of copper functions as catalyst, since this reaction involves fast redox equiUbria where anthraquinone derivatives and copper compounds are concerned. Some evidence indicates that the catalyst is probably a copper(I) compound (28,29). 

A Methylanthrapyridone and Its Derivatives. 6-Bromo-3-methylanthrapyridone [81-85-6] (75) is an important iatermediate for manufacturiag dyes soluble ia organic solvents. These solvent dyes are prepared by replacing the bromine atom with various kiads of aromatic amines. 6-Bromo-3-methylanthrapyridone is prepared from 1-methyl amino-4-bromoanthra quin one (43) by acetylation with acetic anhydride followed by ring closure ia alkaU. The startiag material of this route is anthraquiaoae-l-sulfonic acid (16). 

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