D-Toluidine

When d-toluidines are heated with thionyl chloride in xylene, this ring is formed in good yield. 

Burkett, D. D. Toluidine blue O in vivo stain composition, process of manufacture, and methods of use to identify dysplastic tissue. PCT Int. Appl. WO 9925388, 1999 Chem. Abstr. 1999,130, 349378. 

Figure 12.14 Chromatographic analysis of aniline (a) Precolumn chromatogram (the compound represented by the shaded peak is solvent flushed) (b) main column chromatogram without cryotrapping (c) main column chromatogram with ciyottapping. Conditions DCS, two columns and two ovens, with and without ciyottapping facilities columns OV-17 (25 m X 0.32 mm i.d., 1.0 p.m d.f.) and HP-1 (50 m X 0.32 mm, 1.05 p.m df). Peak identification is as follows 1, benzene 2, cyclohexane 3, cyclohexylamine 4, cyclohexanol 5, phenol 6, aniline 7, toluidine 8, nittobenzene 9, dicyclohexylamine. Reprinted with permission from Ref. (20).

An unusual dimerization reaction was found to occur between anilines and l,4 3,6-dianhydro-D-fmctose 69 under acidic conditions. A 1 1 mixture of 69 with />-toluidine, stirred at room temperature with />-toluenesulfonic acid, rapidly gives the formal dimer, furofuroquinoline 70, as proved by single crystal X-ray diffraction <2005BML1821>. The proposed mechanism for this reaction is shown in Scheme 21. 

Goodman, D.G., J.M.Ward, and W.D.Reichardt. 1984. Splenic fibrosis and sarcomas in F344 rats fed diets containing aniline hydrochloride, p-chloroaniline, azobenzene, o-toluidine hydrochloride, 4,4 -sulfonyldianiline, or D C red no. 9. J. Natl. Cancer Inst. 73 265-273. 

Ward, E., A.Carpenter, S.Markowitz, D.Roberts and W.Halperin. 1991. Excess number of bladder cancers in workers exposed to ortho-toluidine and aniline. J. Natl. Cancer Inst. 83 501-506. 

Fig. 3.154. Electropherogram for the working solution of aromatic amines. Peaks 1 = 4,4 -diamin-odiphenylmethane 2 = 4,4 -oxidianiline 3 = benzidine 4 = aniline 5 = 2,4-diaminoanisole 6 = 2,4 -toluilendiamine 7 = o-toluidine 8 = 3,3 -dimethylbenzidine 9 = 3,3 -dimethoxyben-zidine 10 = p-cresidine 11 = 2-naphtylamine 12 = p-chloroaniline 13 = 4-aminodiphenyl 14 = 1-naphtylamine 15 = 4-chlorotoluidine all at 10 ng/jul. Conditions buffer = 50 mM phosphate 10 per cent methanol pH = 3.1 fused-silica capillary recovered with polyamide, 52 cm X 75 pm i.d. applied potential = +22 kV UV detection at 214 nm. Reprinted with permission from S. Borros et al. [195].

Zayed et al. (1983) studied the degradation of trifluralin by the microbes Aspergillus carneus, Fusarium oxysporum, and Thchoderma viride. Following an inoculation and incubation period of 10 d in the dark at 25 °C, the following metabolites were identified a,a,a-trifluoro-2,6-dinitro-A -propyl-jO-toluidine, a,a,a-trifluoro-2,6-dinitro-p-toluidine, 2-amino-6-nitro-a,a,a-trifluoro-p-toluidine, and 2,6-dinitro-4-trifluoromethylphenol. The reported half-life in soil is 132 d (Jury et al., 1987). 

Aminopropane, see Isopropylamine Amino-2-pyridine, see 2-Aminopyridine a-Aminopyridine, see 2-Aminopyridine o-Aminopyridine, see 2-Aminopyridine 2-Aminotoluene, see o-Toluidine o-Aminotoluene, see o-Toluidine Ammonia anhydrous, see Ammonia Ammonia gas, see Ammonia Amoxone, see 2,4-D... 

Those degradation products which have been identified in our investigations are 1-naphthol from carbaryl, 2,4-D acid and 2,4-dichlorophenol from 2,4-D ester, 2-chloro-2, 6 -diethylacetanilide from alachlor, o,o,oe-trifluro-2-nitro-6-amino-N,N-dipropyl-p-tolu-idine and o,o,o-trifluro-2,6-diamino-N,N-dipropyl-p-toluidine from trifluralin, and a variety of phenols and acids from the degradation of the aromatic solvents used in the formulation of the liquid pesticides as emulsifiable concentrates (41,42). 

The reaction that occurs with Gly-OEt, 3,5,6-tri-O-methyl-D-glucose, p-toluidine, and phenacyl bromide to give 48 (or its regioisomer) represents a particular case (920PP665). 

Cheever, K.L., Richards, D.E. Plotnick, H.B. (1980) Metabohsm of ortho-, meta-, and para-toluidine in the adnlt male rat. Toxicol, appl. Pharmacol, 57, 361-369 Cheever, K.L., DeBord D.G, Sweaiengin, T.F. Booth-Jones, A.D. (1992) ortho-Toluidine blood protein addnets HPLC analysis with fluoreseenee deteetion after a single dose in the adult male rat. Fundam. appl Toxicol, 18, 522-531 Chemfinder (2000) ortiho-Toluidine Hydrochloride [http //www.ehemfinder.com/result.asp] Chemieal Information Serviees (1999) Directory of World Chemical Producers (Version 99.1.0) [CD-ROM], Dallas, TX... 

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