2.4- Diamino-4 - azobenzene

Diamino-azobenzene, CgH. NiN.CgH (NH2)2- Called 2, 4-Di ami no-azobenzol 4-Benzolazo-phenylendiamin or Base des Chrysoidins in Ger. See Chrysordine, Vol... 

Nitro-2, 4-diamino-azobenzene or Nitro ebry so idine,... 

Dinitro-2, 4-diamino-azobenzene, 02N.CgH4.N N.CgH2(N02)(NH2)2 orn-color-ed powd, colors acetate rayon a golden yel, was prepd by coupling 4-nitro-l, 3-diamino-benzene with 4-nitroaniline (Ref 1)... 

NOTE Higher nitrated derivs of Diamino-azobenzene were not found in Beil or in CA thru 1961... 

The development of the "sulfa drugs,"a c derivatives of sulfanilamide, originated with studies of the staining of protozoal parasites by Paul Erhlich. In 1932 it was shown that the red dye 2,4-diamino-azobenzene-4 -sulfonamide (Prontosil) dramatically cured systemic infections by gram-positive bacteria. Subsequent studies revealed that bacteria converted... 

Chahidi C, Giraud M, Aubailly M, Valla A, Santus R. 2,4-Diamino-6-pteridinecarboxyaldehyde and an azobenzene derivative are produced by UV photodegradation of methotrexate. Photochem Photobiol 1986 44 ... 

Berg et al. synthesized peptide oligomers that incorporated 4-cyanoazobenzene for erasable holographic data storage [168]. The oligomer is a diamino acid-N -substituted peptide (DNO) repeat unit, compound 4, with an azobenzene side chain... 

Chry sordine (Di amino azobenzene or 4-Phenylazo -m-phenylene diamine Hydrochloride) [called 2,4 -Diamino-azobenzol 4-Benzolazo-phenylenediamin -(I.3) or Base des Chrysoidins in Ger]. C Hg. NiN.CgHgOSfHj) mw 212.25. N 26.40% yel ndls (from hot w), mp 117.5° s l rlc, eth, chlf, benz or aniline si sol in hot w. It forms numerous salts which are cryst comds. The Hydrochloride (also called Chrysoidine Y or Chrysoidine Extra), Cl H 2 4 HCl, red-bm powd or large, black shiny crysts having a green luster, is the commercial product. The Dibydrochloride, col crysts (from ale), dec at 222°. Other props methods of prepn are given in Ref 1... 

Nitro-2, 4 diamino-azobenzene, above formula, red-gtn shiny ndls (from Nitrobenz or benzene homologes), mp 230° readily sol in acet, pyridine glacial AcOH si sol in ale eth (Ref 2). Kul berg Sc Ivanova (Ref 5) detd the color reaction of this compd in Mg salts... 

Dinitro-4, 4 -diamino-azobenzene, H2N.(02N).C(5H3.N N.C6H3(N02).NH2 red plates or orn ndls (from phenol + ethanol), rap 340-41° was obtd by hydrolysis with H2SO4 of 4, 4 -diacetamido-3, -dinitro-azobenzene, itself obtd by coupling of 2-nitro-4-nitrosoacetanilide 4-amino-2-nitroacetanilide in acetic acid (Ref 2)... 

This approach requires that the polymer or an additive contains a chromophore that changes the wavelength of its absorption maximum as the reactive processing proceeds. In one well-studied example of the addition of a low concentration of a probe molecule, />,/> -diamino azobenzene (DAA - Scheme 3.2), to an epoxy resin, the probe actually participates in the... 

The />,/> -diamino azobenzene (DAA) reactivity probe, described in the previous section, has been demonstrated to form reaction products with DGEBA-based epoxy resins that have a greater fluorescence intensity than does DAA itself. By examining model adducts with phenyl glycidyl ether, the intensity enhancement varied from 1400 times to 9 times depending on whether the DAA reacted at a crosslink or a chain end, respectively... 

The dyes of this class are derived from aromatic azo compounds, such as azobenzene, CeHs—N = N—CeHs. They are prepared by treating a diazonium salt with an amine or a phenol. Thus, if a solution of m-phenylene diamine is added to a dilute solution of benzene-diazonium chloride, the hydrochloride of diamino-azobenzene, which is the dye chrysoidine, is formed —... 

Diamino-4 -(4-nitrophenyl-diazenyl)azobenzene 4-(4 -Nitrophenyl-diazenyl)phenyl-l,3-diamine... 

The synthesis and gelation properties of compounds 52-55, containing aromatic chromophores, were reported (Scheme 21). The central unit A of gela-tor 52 is based on two azobenzene chromophores that are connected by a central flexible diamino chain [76]. This compound was observed to gelate various organic solvents, such as 1-hexanol, 1-octanol, toluene, m-xylene, and p-xylene, under 1.0-5.0wt%. As observed in the case of ALS systems, CD spectroscopy pointed to the chiral orientation of 52 molecules within the gel aggregate and TEM photographs showed the occurrence of helical fibers. 

Of all the compounds prepared before 1909, product No. 606 proved to be particularly effective against syphilis. It was marketed as Salvarsan in Europe, and was known as Arsphenamine in the U SA. It was originally thought that this compound was an arsenic analog of azobenzene it was represented as 1, a dimer with an -As=As- double bond and designated as 3,3 -diamino-4,4 -dihydroxy-arsenobenzene (Scheme 1.4). 

---