Ortho-Toluidine

NB Other relevant data taken into consideration in making the overall evaluation) Tetrachloroethylene [127-18-4] (Vol. 63 1995) ortho-Toluidine [95-53-4] (Vol. 27, Suppl. 7, Vol. 77 2000)... 

Acylation of ortho-toluidine with 2-bromopropionyl bromide Ifords the haloamide (73). Displacement of the halogen by ii uns of butylamine affords prilocaine (74). ... 

Inorganic nickel compounds arising during the refining of nickel Ortho-toluidine... 

Hexamethylene tetramine Mercapto benzo thiazole Ortho-toluidine Para-toluidine... 

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. 

Sellers C, Markowitz S Reevaluating the carcinogenicity of ortho-toluidine a new... 

N-METHYL-ORTHO-TOLUIDINE N-METHYl-PARA-TOLUIDINE N, N-DIME PHYL-ORTHO-a OLUIDINE 2.4-XYLIDINE N, N-... 

The use of activated anthranihc acid derivatives facUitates the preparation of the amides in those cases where the amines are either umeactive or difficult to obtain. Thus, reaction of (87-1) with phosgene gives the reactive the isatoic anhydride (89-1). Condensation of that with ortho-toluidine leads to the acylation product (89-2) formed with a simultaneous loss of carbon dioxide. This is then converted to the quinazolone (89-3) by heating with acetic anhydride. Reaction with sodium borohydride in the presence of aluminum chloride selectively reduces the double bond to yield the diuretic agent metolazone (89-4) [99]. 

Reacting ort/20-chlorotoluene with sodium in liquid ammonia generates a mixture of 67% ort/to-toluidine and 33% raeta-toluidine (Lin Krishnamurti, 1993). ortho-Toluidine can also be produeed by reduction of ort/zo-nitrotoluene or obtained mixed with / ara-toluidine by reduetion of erude nitrotoluene (Lewis, 1993). 

Information available in 1999 indicated that ort/jo-toluidine was manufactured by 16 companies in China, 11 companies in India, six companies in the United States, three companies each in Germany and Russia, two companies each in Japan and Poland, and one company each in Brazil, France, Italy, Mexico, Romania and Spain, and that ortho-toluidine hydrochloride was manufactured by one company each in Germany and India (Chemical Information Services, 1999). 

According to the 1981-83 National Occupational Exposure Survey (NOES, 1999), as many as 30 000 workers in the United States were potentially exposed to ortho-toluidine and its hydrochloride salt (see General Remarks). Occupational groups included workers in the chemical industry, laboratory workers, machine operators and cleaners and janitors. Ninety laboratory workers, health-care workers and university teachers were identified as exposed to ort/20-toluidine or its salts in the Finnish Register of Employees Exposed to Carcinogens in 1997 (Savela et a/., 1999). National estimates of workers exposed were not available from other countries. 

A bladder cancer incidence study was conducted among workers exposed to ortho-toluidine at a plant manufacturing rubber chemicals in New York State, United States. The study was initiated at the request of the union representing workers at the plant, who had noted a number of bladder cancers among workers in a department where an... 

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... 

Environmental Protection Agency (1984) Chemical Hazard Information Profile ortho-Toluidine, ortho-Toluidine Hydrochloride, Washington DC, Office of Pesticide Program and Toxic Substances... 

Sellers, C. Markowitz, S. (1992) Reevaluating the carcinogenicity of ortho-toluidine a new conclusion and its implications. Regul. Toxicol. Pharmacol., 16, 301-316 de Serres, F.J. Ashby, J., eds (1981) Progress in Mutation Research, Volume 1, Evaluation of Short-Term Tests for Carcinogens. Report of the International Collaborative Program, Amsterdam, Elsevier... 

Prilocaine is an amide-type LA with a rapid onset and an intermediate duration of action associated with a low toxicity. However, metabolism to ortho-toluidine can cause oxidation of the ferric form of hemoglobin to the ferrous form, creating methemoglobin. In most cases the methemoglobuniemia is benign, but sometimes tissue hypoxia is observed (Eriksson, 1966). 

Povidone-iodine gives a positive reaction with an ortho-toluidine reagent used to detect blood in the urine, for example Hematest reagent tablets or dipsticks (SEDA-11, 488 47). 

One mol of a-bromopropio-ortho-toluidine is mixed with a solution of 3 mols of n-propylamine in 500 ml of water-free benzene and the reaction mixture is heated in an autoclave to 80°C for 8 hours. After cooling the reaction mixture is treated as described above. The base is obtained as a colorless oil. BP 159°-162°C/0.1 mm. Yield 55%. The base is then converted to the hydrochloride by reaction with HCI. 

D.G. DeBord et al., Binding characteristics of ortho-toluidine to rat hemoglobin... 

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