Cloreto isocianúrico e cloreto cianúrico: aspectos gerais e aplicações em síntese orgânica

Cunha, Anna C.; Paixão, Fernanda Menezes da; Souza, Maria Cecília B. V. de; Ferreira, Vı́tor F.

doi:10.1590/s0100-40422006000300021

Cited by 7 publications

(8 citation statements)

References 28 publications

(37 reference statements)

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“…Este reagente, largamente aplicado na desinfecção de águas de piscinas e no tratamento de águas em geral, conhecido comercialmente como Simclosene, Genclor, Cloreal ou ACL-85 3 , é barato e tem se mostrado um agente eficaz de cloração de núcleos aromáticos 5,6 . Neste trabalho descreve-se a preparação de para-cloroanilina a partir de anilina, usando o ácido tricloroisocianúrico como agente halogenante, em condições brandas.…”

Section: Introductionunclassified

Preparo da para-cloroanilina: um experimento simples, rápido e barato

et al. 2008

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Recebido em 21/11/06; aceito em 21/6/07; publicado na web em 19/12/07 PREPARATION OF para-CHLOROANILINE: A SIMPLE, FAST AND INEXPENSIVE EXPERIMENT. Experiments simple, short and efficient for experimental disciplines in undergraduate courses in Chemistry are an excellent opportunity for students to consolidate the learning of theoretical concepts in classical chemical transformations. The use of a safe reagent, of low cost and easy access is the motivation for this communication, that describes the use of trichloroisocyanuric acid -a chlorinating agent used in the treatment of swimming pool water -for the chlorination of acetanilide, an intermediate in the preparation of para-chloroaniline.Keywords: chlorination; para-chloroaniline; trichloroisocyanuric acid. INTRODUÇÃONos últimos anos é cada vez maior, nos cursos de Química e áreas afins, a preocupação com a não agressão ao meio ambiente. Nestes cursos vem se procurando, sempre que possível, introduzir nas disciplinas experimentais práticas nas quais os estudantes manipulem reagentes químicos de baixa toxidez, baratos, que levem a bons rendimentos nas reações onde são empregados, que não envolvam o uso de solventes orgânicos, principalmente clorados, e que não gerem resíduos, ou os gerem em pequenas quantidades 1 . Neste artigo propõe-se o uso do ácido tricloroisocianúrico (1) para a cloração da acetanilida. Em revisões recentes Barros2 , Cunha e colaboradores 3 e Rodrigues e colaboradores 4 descreveram aplicações do ácido tricloroisocianúrico -ATCI em síntese orgânica. Este reagente, largamente aplicado na desinfecção de águas de piscinas e no tratamento de águas em geral, conhecido comercialmente como Simclosene, Genclor, Cloreal ou ACL-85 3 , é barato e tem se mostrado um agente eficaz de cloração de núcleos aromáticos 5,6 . Neste trabalho descreve-se a preparação de para-cloroanilina a partir de anilina, usando o ácido tricloroisocianúrico como agente halogenante, em condições brandas. Este reagente, por ser sólido, de baixo custo e de fácil manuseio, tem diversas vantagens sobre outros agentes de halogenação, principalmente o cloro, devido à toxicidade deste gás e sobre outros agentes de cloração como a Nclorosuccinimida e N-clorosacarina 7 , por estes serem reagentes importados e mais caros.A cloração de compostos orgânicos utilizando cloro em fase gasosa é bastante trabalhosa e perigosa. Como descrito por Vogel 8

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Section: Introductionunclassified

Preparo da para-cloroanilina: um experimento simples, rápido e barato

et al. 2008

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“…The presence of chlorine, an indication of possible residue from trichloroisocyanuric acid, was detected only in trace amounts in some of the analytes and should not interfere with the spectra of the analytes (the presence of chlorine was verified using very sensitive Feigl tests). 23 On the one hand, the results from the 13 C NMR spectra of a group of analytes in solution described in this paper showed that they had only one peak with practically equal chemical shifts. On the other hand, the bar infrared data of the respective solid analytes differ quite massively.…”

Section: Nmr Of the White Precipitatesmentioning

confidence: 76%

“…A prompt answer was provided by obtaining 13 C NMR spectra of the analytes dissolved in DMSO. The chemical shifts recorded for these analytes are presented in Table 2.…”

Section: Nmr Of the White Precipitatesmentioning

confidence: 99%

“…The spectra of solid 13 C NMR for the complete set of analytes in this paper are more complex, and the discussion of these spectra will be presented in another publication jointly with other data.…”

Section: Nmr Of the White Precipitatesmentioning

confidence: 99%

“…7 This compound is extensively used as a disinfectant agent for swimming pools (algicide and bactericide). 8 Presently, TCI is also widely employed as an effective chlorinating reagent for various chemical reactions, such as the α-chlorination of carbonyl derivatives, 9 the production of nitriles from amines, 10 the halogenation and epoxidation of alkenes, 11 and the chlorination of aromatic systems, 5,12 among others; extensive reviews on the reactions of TCI have been offered by Tilstan and Weinmann, 4 Cunha and Ferreira 13 and Mendonça and Mattos. 14 Figure 1 shows the chemical structures of these molecules.…”

Section: Introductionmentioning

confidence: 99%

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Using Bar Infrared Spectra and Coincidence Indexes to Study the Diversity of Solid Cyanuric Acid Structures

Nilo¹,

Simões²,

Neto³

2018

J. Braz. Chem. Soc.

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A general method was developed for studying the diversity of individuals in a population based on the diversity of infrared spectra of solid cyanuric acid analytes obtained from various reactions of trichlorocyanuric acid. This method first generates infrared bar spectra for the analytes and then measures the coincidence and continence among pairs of the spectral peaks via confrontation matrices. Class markers are established to characterize analyte classes. Possible correlations among the employed reaction conditions and the nature of the produced solids, which are based on their infrared bar spectra, are discussed. The method of coincidence may be useful for characterizing polymorphs, particularly those of active pharmaceutical ingredients (APIs). The method may also be extended to define the homogeneity of solid analytes. The ANALIN module of the ANALOR software suite running on a dBase platform is used to generate the bar infrared spectra and to handle all calculations.

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Room‐Temperature Electrophilic 5‐endo‐dig Chlorocyclization of Alk‐3‐yn‐1‐ones with the Use of Pool Sanitizer: Synthesis of 3‐Chlorofurans and 5‐Chlorofuropyrimidine Nucleosides

et al. 2008

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The 5-endo-dig chlorocyclization of 1,4-disubstituted alk-3-yn-1-ones (propargylic ketones) with the use of trichloro-striazinetrione (trichloroisocyanuric acid, TCCA; 0.4 equiv.) in toluene, at room temperature, in the absence of base, provides 2,5-disubstituted 3-chlorofurans in high yields (79-96 %). The reaction can be accomplished by using commercially available swimming pool sanitizer. Selected 3-chlo-

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Cloreto isocianúrico e cloreto cianúrico: aspectos gerais e aplicações em síntese orgânica

Cited by 7 publications

References 28 publications

Preparo da para-cloroanilina: um experimento simples, rápido e barato

Preparo da para-cloroanilina: um experimento simples, rápido e barato

Using Bar Infrared Spectra and Coincidence Indexes to Study the Diversity of Solid Cyanuric Acid Structures

Room‐Temperature Electrophilic 5‐endo‐dig Chlorocyclization of Alk‐3‐yn‐1‐ones with the Use of Pool Sanitizer: Synthesis of 3‐Chlorofurans and 5‐Chlorofuropyrimidine Nucleosides

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