8-Hydroxy-7- -5-sulfo

Pyridin 3-Hydroxy-5-hydroxy-methyl-4-(hydroxy-sulfo-me-... 

All salts and buffer components, as well as poly-D,L-lysine (PL), CBZ-protected PL, diethylene triamine penta-acetic acid (DTPA) and its anhydrides, water-soluble carbodiimide (l-ethyl-3-(dimethylaminopropyl)-carbodiimide, EDC), (SPDP), SMCC, dithiothreithol, succinic anhydride, trinitrobenzene sulfonic acid, triethylamine, bovine serum albumin (BSA), and IV-hydroxy sulfo-succinimide (HSSI) are available from Sigma (St. Louis, MO). 

The classic preparation method of sulfo betaines utilizes the conversion of tertiary amines with propane sultone. Hydroxy sulfo betaines amino oxides are obtained from tertiary amines and chloro hydroxypropane sulfonic acid [32-34]. 

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). 

Naphthol AS Coupling Components. Naphthol AS components are the aryhdes of either o-hydroxyarylcarboxycHc acids or acylacetic acids. They are free of sulfo and carboxyl groups, but form salts with bases these salts dissolve in water to give colloidal solutions, which couple with diazo components to form colored pigments. The whole class derives from the anilide of 3-hydroxy-2-naphthoic acid [92-70-6] Naphthol AS (85) (Cl Azoic Coupling Component 2). 

Calcon carboxylic acid [3-hydroxy-4-(2-hydroxy-4-sulfo-l-napbtbylazo)napbtbalene-2-carboxylic acid] [3737-95-9] M 428.4, m 300°, X,max 560nm, pKj 1.2, pK2 3.8, PK3 9.26, PK4 13.14. Purified through its p-toluidinium salt. The dye was dissolved in warm 20% aq MeOH and treated with p-toluidine to ppte the salt after cooling. Finally recrystd from hot water. [Itoh and Ueno Analyst (London) 95 583 1970.] Patton and Reeder (Anal Chem 28 1026 1956) indicator and complexes with Ca in presence of Mg and other metal ions. 

For arene- and heteroarenediazonium ions with substituents that are subject to their own acid-base equilibria the situation is more complex. For example, the hydroxy group of the 4-hydroxybenzenediazonium ion has a pAfa value of 3.40 (Lewis and Johnson, 1959) whereas the 2-hydroxy-5-sulfo-benzenediazonium zwit-terion has a pATa value of only —0.04 (Jermini et al., 1970). The 0 group of the conjugate base greatly reduces the acidity of the diazonio group, as indicated by the mesomeric quinonediazide structure in Scheme 5-13. 

Hydroxy-naphthaline reagieren ausschlieBlich zu l-Arylazo-2-hydroxy-naph-thalinen(vgl. Band X/3, S. 276). Peri-standige Substituenten- besonders die Sulfo-Grup-pe - beeintrachtigen die Kupplung mit schwacher elektrophilen Diazonium-Salzen, wah-rend starker elektrophile Diazonium-Salze nicht beeinfluBt werden. 

Die Kinetik der Kupplung von 4-Nitro-phenyldiazonium-SaIzen in Gegenwart von Oberfliichen-aktiven Substanzen wurde untcrsucht1. Die Reaktionen von 2-Hydroxy- und 2-Hydroxy-6-sulfo-naphthalin waren mit 4-[(Dimethyl-hexadecyl-ammoniono)-methyl]-phenyldiazonium-dibromid t22 bzw. 244mal schneller (pH = 7) als mit der Vergleichsverbindung 4-(Dimethylamino-methyl)-phcnyldiazoniumbromid2. 

---