4,4 -diaminodiphenyl =• benzidine

In the presence of acids, hydrazobenzene rearranges to give about 0 per cent, of benzidine (4 4 -diaminodiphenyl) and about 30 per cent, of diphenyline (2 4 -diaminodiphenyl) ... 

The conversion of a hydrazobenzene into a diaminodiphenyl upon treatment with acid is termed the benzidine rearrangement. The following mechanism for the formation of benzidine from hydrazobenzene appears reasonable ... 

Historically, bladder tumors have been associated with exposures in the aniline dye industry. However, conclusive evidence for any one particular exposure could not be obtained in these studies since the workers were exposed to many chemicals within the same work area. For example, Case et al. (1954) investigated the incidence of bladder tumors among British workers in the chemical dye industry. In addition to aniline, the workers were exposed to other aromatic amines, including a- and P-naphthylamine, benzidine, and auramine. Although exposures could not be quantified, there was insufficient evidence to suggest that aniline was a cause of bladder cancers. More recent studies indicate that P-naphthylamine, 4-aminodiphenyl, 4-nitrodiphenyl, 4,4-diaminodiphenyl, or o-toluidine may be involved in increased cancers in the dye industry (Ward et al. 1991 Benya and Cornish 1994). 

Numerous linear diamines, such as many of those in the survey mentioned above, have been evaluated as potential replacements for benzidine, an inexpensive and highly versatile intermediate that was banned in the 1970s because it posed a carcinogenic threat. Two trisazo dyes have been synthesised recently using 4,4, diaminodiphenyl thioether instead of the benzidine component of Cl Direct Black 38 (3.112 X = Y = NH2) and Cl Direct Green 1 (3.112 X = OH, Y = H). These new dyes exhibited higher substantivity and fastness to washing than the two traditional products on cellulosic fibres [119]. 

Synonyms AI3-00140 Azoic diazo component 112 Benzidine base p-Benzidine Benzioine 4,4 -Bianiline p,//-Bianiline (l,l -Biphenyl)-4,4 -diamine 4,4 -Biphenyldiamine p,//-Biphenyl-diamine 4,4 -Biphenylenediamine p,//-Biphenylenediamine BRN 0742770 CCRIS 71 C.I. 37225 C.I. azoic diazo component 112 4-Diaminodiphenyl jo-Diaminodiphenyl 4,4 -Diamino-biphenyl p,//-Diaminobiphenyl 4,4 -Diamino-l,l -biphenyl 4,4 -Diaminodiphenyl p.p -Di-aminodiphenyl 4,4 -Dianiline p,/y-Dianiline 4,4 -Diphenylenediamine p,//-Diphenylenedi-amine EINECS 202-199-1 Fast corinth base B NCI-C03361 NSC 146476 RCRA waste number U021 UN 1885. 

Developer 13, see p-Phenylenediamine Developer P, see 4-Nitroaniline Developer PF, see p-Phenylenediamine Devicarb, see Carbaryl Devikol, see Dichlorvos Devol orange B, see 2-Nitroaniline Devol orange R, see 3-Nitroaniline Devol orange salt B, see 2-Nitroaniline Devol red GG, see 4-Nitroaniline Devoran, see Lindane Devoton, see Methyl acetate Diacetone, see Diacetone alcohol Diacetonyl alcohol, see Diacetone alcohol Diakon, see Methyl methacrylate Dialene 6, see 1-Hexene 1,4-Diaminobenzene, see p-Phenylenediamine p-Diaminobenzene, see p-Phenylenediamine 4-Diaminodiphenyl, see Benzidine p-Diaminodiphenyl, see Benzidine 4,4 Diaminobiphenyl, see Benzidine p,p -Diaminobiphenyl, see Benzidine 4,4 -Diamino-l,l -biphenyl, see Benzidine 4,4 -Diamino-3,3 -dichlorobiphenyl, see 3,3 -Dichloro-benzidine... 

Reaction LI. (a) Action of Acids on the non-para substituted Hydrazo Compounds. (A., 270, 330 287, 97 B 26, 681, 688, 99.)—When hydrazobenzene is treated with mineral acids, an intermolecular rearrangement to benzidine (pj-pg-diaminodiphenyl) takes place. 

Primary disazo dyes of the type K <—D —>K2 (Ki = K2 or K i K2). This series includes many milling dyes because of the molecular size achieved (group C). Depending on the type of coupling components Ki and K2, which may be phenols, pyrazolones, acetoacetic acid arylamides, or naphtholsulfonic acids, clear yellow to red shades are obtained. For a long time the preferred diazo components were diaminodiphenyl derivatives, such as benzidine, o-tolidine and o-anisidine. They are now of no further importance because of their carcinogenic potential. 

Benzidine (4,4-Biphenyldiamine, 4,4-Diaminobiphenyl, p-Diaminodiphenyl) Molecular formula NH2C6H4NH2... 

Benzidine acetate (0-05 %). Dissolve 0 05 g benzidine (4-4/-diaminodiphenyl), H2N.C6H4.C6H4.NH2, in 100ml of 2m acetic acid. (DANGER THE REAGENT IS CARCINOGENIC.)... 

The benzidine rearrangement involves the action of strong mineral acids on hydrazobenzene to form 4,4 -diaminodiphenyl, or benzidine. 

The benzidine rearrangement was employed recently for the preparation of unique bridged diaminodiphenyls 130 and 131227,228. An unprecedented [9,9]-sigmatropic shift was discovered in the acid-catalyzed benzidine rearrangement of bis[4-(2-furyl)phenyl]... 

Synonyms/Trade Names Benzidine-based dyes 4,4 -Bianiline 4,4 -Biphenyldiamine 1,r-Biphenyl-4,4 -diamine 4,4 -Diaminobiphenyl p-Diaminodiphenyl [Note Benzidine has been used as a basis for many dyes] ... 

Benzidine, 3,3 -dimethoxy. See Dianisidine Benzidine, 2,2 -disulfo-. See 2,2 -Benzidinedisulfonic acid 2,2 -Benzidinedisulfonic acid CAS 117-61-3 EINECS/ELINCS 204-200-0 Synonyms Benzidine, 2,2 -disulfo- Benzidine-2,2 -disulfonic acid 6,6 -Bimetanilic acid (1,1 -Biphenyl)-2,2 -disulfonic acid, 4,4 -diamino- 2,2 -Biphenyldisulfonic acid, 4,4 -diamino-4,4 -Biphenyldisulfonic acid, 2,2 -diamino- 2,2 -Diamino-4,4 -biphenyldisulfonic acid 4,4 -Diamino-(1,1 -biphenyl)-2,2 -disulfonic acid 4,4 -Diaminobiphenyl-2,2 -disulfonic acid 4,4 -Diaminodiphenyl-2,2 -disulfonic acid 2,2 -Disulfobenzidine 2,2 -Disulfo-4,4 -diaminobiphenyl Empirical C12H12N2O6S2... 

Benzidine dihydrochloride hardener, PWB laminates 4,4 -Diaminodiphenyl sulfone hardener, resins... 

Bedekar and co-workers [4] characterised a series of polyaromatic diamines including polymers of o-chloroaniline, benzidine, 4,4 diaminodiphenyl ether and diaminodiphenyl methane using a variety of techniques including X-ray photoelectron spectroscopy, Fourier transform infrared (FTIR) spectroscopy, and elemental analysis. They found that polymers of diamine compounds had an additional S and O in the form of sulfate ions in the polymer matrix. 

Polyimides are manufactured from diamines and dianhydrides. The created polymer structure causes differences in hydrolysis resistance, while thermal resistances are comparable. Thus, polyimides made from pyromellitic acid-dianhydride (PMDA) and diaminodiphenyl ether (ODA) or diaminodiphenyl thioether (SDA), respectively exhibit excellent hydrolysis resistance, while polyimides made from PMDA and m-phenylenediamine (MPD), p-phenylenediamine (PPD), or benzidine have very poor resistance and were therefore not developed further [723]. 

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