L-Amino-6-naphthalenesulfonic acid

Another example of manufacture in this series is the sulfonation of an aminonaphthalenesulfonic acid, followed by selected desulfonation, to make 6-amino-l,3-naphthalenedisulfonic acid (21). Thus, 2-amino-l-naphthalenesulfonic acid made by amination of 2-hydroxy-1-naphthalenesulfonic acid is added to 20 wt % oleum at ca 35°C. At this temperature, 65 wt % oleum is added and the charge is stirred for 2 h, is then slowly heated to 100°C and is maintained for 12 h to produce 6-amino-l,3,5-naphthalenetrisulfonic acid. The mass is diluted with water and maintained for 3 h at 105°C to remove the sulfo group adjacent to the amino group. After cooling to ca 20°C and filtration, 6-amino-l,3-naphthalenedisulfonic acid is obtained in 80% yield (55). 

An infinite ID complex [Ag( 14)( 15) with a single-stranded helical chain structure was obtained through the reaction of 6-amino-1-naphthalenesulfonic acid (H-14) and 2-methylpyrazine (15) with Ag2CC>3.58 Furthermore, when tetra- and hexaethyleneglycol-spaced ligands, 1,1 l-(3,6,9-trioxaundecane)diyl-bis(nicotinate) (16) and l,17-(3,6,9,12,15-pentaoxaheptadecane)diyl-bis(nicotinate) (17), were reacted with silver salts, double-stranded helical complexes (as exhibited in Fig. 11.24) were formed.59... 

Direct dyes are defined as anionic dyes substantive to cellulosic fibers (cotton, viscose, etc), when applied from an aqueous bath containing an electrolyte. Before the discovery of Congo Red in 1884, only mordanted cotton could be dyed. Congo Red [573-58-0] (62) (Cl Direct Red 28 Cl 22120), a primary symmetrical disazo dye, which is made readily from bisdiazotized benzidine and naphthionic acid [84-86-6] (4-amino-l-naphthalenesulfonic acid), was the precursor of a most important line of dyes, including all shades, derived from benzidine and its homologues. Today, no benzidine dye is produced because benzidine is carcinogenic. 

Fig. 5. Direct red dyes, (a) Direct Red 81 described in text (68) (b) Direct Red 2 (o-tolidine coupled to two moles of naphthionic acid) (69) (c) Direct Red 23 (aniline coupled to 6,6,-ureylenebis-l-naphthol-3-sulfonic acid with a second coupling with />-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-amino-w-toluenesulfonic acid coupled under acidic conditions to 6,6,-ureylenebis-l-naphthol-3-sulfonic acid followed by an alkaline coupling of 0-anisidine) (71) (d) Direct Red 72 (Broenner s acid, ie, 6-amino-2-naphthalenesulfonic acid coupled under acidic conditions to 6,6 -ureylenebis-l-naphthol-3-sulfonic acid followed by an...

Sulfonation of / -naphthylamine leads to somewhat more precise orientation of the substituents. When special attention is paid to conditions such as temperature and S03 content of the sulfonation mixture, either 6- and 7-amino-l-naphthalenesulfonic acid or 6- and 7-amino-2-naphthylaminesulfonic acid can be obtained. When the concentration of S03 is increased, di- and tri-sulfonic acids of jS-naphthylamine are formed from the monosulfonic acids.151,152... 

A particularly important class of coupling components are the aminohydroxy-naphthalenesulfonic acids. Appropriate variation of the disazo component permits the development of shades ranging from orange to black. Orange and scarlet are achieved with I-acid (6-amino-l-hydroxy-naphthalene-3-sulfonic acid) and y-acid (7-amino-1-hydroxynaphthaIcne-3-sulfonic acid), whereas H-acid (8-amino-l-hydroxynaphthalene-3,6-disulfonic acid) and K-acid (8-amino-l-hydroxy-naphthalene-3,5-disulfonic acid) derivatives are useful for red to bluish-red hues. Extremely lightfast red shades are also accessible with disazo dyes ( brown dyes ). For chemical structures see Section 3.1.5). 

Although Barcelo et al. [129] focused on the performance of solid phase extraction materials, the analyte base of 22 aromatic sulfonates (e.g., benzenesul-fonate, 2-amino-1,5-naphthalenedisulfonate, 1,3-benzenedisulfonate, l-hydroxy-6-amino-3-naphthalenesulfonate, 2-napthalenesulfonate, diphenylamine-4-sulfonate) is extensive. Separation is achieved on a Cjg column using a complex 30-min 100/0 25/75 water (5mM triethylamine with 5mM acetic acid to pH 6.5)/... 

Amino-5-hydroxy-6-[ 2-hydroxy-3,5-dinitrophenyl)azo]-l-naphthalenesulfonic acid, 9CI. C.I. Mordant green 14. C.I. 17125. Chrome fast green GW. Metachrome green G... 

Hydroxy-4-[ 4-methylpheny[)amino]-6-[ 2,3,5-trichloro-6-hydroxyphenyl)azo]-l-naphthalenesulfonic acid. 8-p-Toluidino-2- 3,5,6-trichloro-2-hydroxyphenylazo)- 1-naphthol-5-sulfonic acid. Omega chrome blue green BL. Metomega chrome blue green BL. C.I. 17650... 

The naphthylamine is treated with a four- to eight-fold excess of sodium hydrogen sulfite in an aqueous medium at 90-150° for 6-30 hours, the time required varying from case to case this affords the l,2,3,4-tetrahydro-4-oxo-2-naphthalenesulfonic acid which is stable in an acid or neutral medium but decomposes in alkali to sulfite and the naphthol 565 yields are almost quantitative. Moreover, 5-quinolinamine has been converted into 5-quinolinol by this route.566 The reaction fails, however, if there is a sulfo group in the meta-position to the amino group. 

Amino-3-hydroxybutyric acid a-Amino-P-hydroxybutyric acid L-2-Amino-3-hydroxybutyric acid. See L-Threonine 6-Ami no-4-hydroxy-5-((a,a,a-trifluoro-o-tolyl) azo)-2-naphthalenesulfonic acid, monosodium salt. See Acid red 337... 

Naphthalenesulfonic acid, 6-amino-4-hydroxy-5-((2-(trifluoromethyl) phenyl) azo)-, monosodium salt. See Acid red 337 Naphthalenesulfonic acid, bis-(l-methylethyl)-, sodium salt. See Sodium isopropyl naphthalene sulfonate... 

On Cleve s acid (l-amino-6-naphthalenesulfonic acid). tOn nerolin (2-methoxynaphthalene). 

Iodoacetyl)amino]ethyl]aminoj-1 -naphthalenesulfonic acid, 1-00038 2-Iodo-A -1 -pyrenylacetamide, 1-00051 2-Iodo-A -(2, 4, 5, 7 -tetrabromo-3, 6 -dihydroxy-3-oxospiro[isobenzofuran-l(3/0 9 [9//]xanthen]-5-yl)acetamide, 1-00054... 

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