Halogenation Halogen benzoic acids

Gerritse J, BJ van der Woude, JC Gottschal (1992) Specific removal of chlorine from the ortho-position of halogenated benzoic acids by reductive dechlorination in anaerobic enrichment cultures. FEMS Microbiol Lett 100 273-280. 

Muccini, M., Layton, A.C., Sayler, G.S., and Schultz, T.W. Aquatic toxicities of halogenated benzoic acids to Tetrahymena pyriformis, Bull. Environ. Contam. Toxicol, 62(5) 616-622, 1999. 

Of the several methods described for the production of thiosalicylic acid, only the following are of preparative interest heating of o-halogenated benzoic acids with an alkaline hydrosulfide at i50-200° in the presence of copper or copper salts,1 5 or by substitution of sodium sulfide at 200° 2 by reduction of dithiosalicylic add with glucose,3 or metals 4,5 in alkaline solution. The dithiosalicylic add is prepared by treating diazo-tized anthranilic acid with sodium disulfide in alkaline solution.4... 

D and 2,4,5-T (Fig. 3) are among the most widely known and used phenoxy alkanoic acids. Teratogenic (fetus deforming) effects on rats and mice were reported for 2,4,5-T and the isooctyl ester of 2,4-D, while mortality and physical abnormalities were shown to increase in chick embryos of gamebird eggs sprayed with 2,4-D at rates commonly used in field applications [92,100]. The most extensively used halogenated benzoic acid herbicides are Chloramben and Dicamba. 

Under photostimulation conditions, o-halogenated benzoic acid has been doubly car-bonylated to give phthalonic acid catalyzed by cobalt carbonyl complex. ... 

In addition to the examples described previously, a tremendous variety of compounds have been prepared using palladium-catalyzed cross-coupling reactions due to the broad functional group tolerance. The combination of copper and palladium complexes have been used to promote the formation of borane-protected arylphosphines [298]. Palladium acetate catalyzed the coupling of halogenated benzoic acid derivatives leading to the formation of water-soluble phosphine ligands [299]. Aryl triflates have also been used in the phosphination reaction [300]. Functionalized tyrosine derivatives were converted... 

Contains Halogen.—Halogen compounds may be n/ly/em aryl or add haUdc tQ ha/oyru aethylene bromide, btomoben/ene, benzoyl cbloiide, oi rhloio-benzoic acid). 

By introducing reasonable values (about 2 for nitrogen, 4 for oxygen) for the electron affinity parameter relative to carbon, 8, and for the induced electron affinity for adjacent atoms (32/8i = Vio), we have shown that the calculated permanent charge distributions for pyridine, toluene, phenyltrimethylammonium ion, nitrobenzene, benzoic acid, benzaldehyde, acetophenone, benzo-nitrile, furan, thiophene, pyrrole, aniline, and phenol can be satisfactorily correlated qualitatively with the observed positions and rates of substitution. For naphthalene and the halogen benzenes this calculation does not lead to results... 

Benzoic acid and esters of p-hydroxybenzoic acid Bronopol Chlorhexidine Formaldehyde Glutaraldehyde Halogens Hexachlorophane Mercurials... 

Hughes DE (1965) The metabolism of halogen-substituted benzoic acids by Pseudomonas fluorescens. Biochem J 96 181-188. 

Reineke W, H-J Knackmuss (1978) Chemical structure and biodegradability of halogenated aromatic compounds. Substituent effects on 1,2-dioxygenation of benzoic acid. Biochim Biophys Acta 542 412-423. 

Zr(allyl)3Br gives mainly, but not exclusively, a center of type (XV). This follows from the observation that reaction of Zr(allyl)3Br with silica gives two molecules of propene per metal atom and no halogen is liberated. Addition of excesses of n-butanol to the SiCb/Zrfallyl Br reaction product however gives one molecule of propene per metal atom and one molecule of HBr per metal atom is liberated with excess benzoic acid solution. The structure of (XVI) was determined in a similar manner. Chromium allyls give transition metal centers with structure (XVII). 

Maurer and Bohme62 reported that one mole of XIV, with acid chlorides in acid solution or with dry hydrogen chloride in ether, adds on halogen acid with the simultaneous production of two moles of benzoic acid per... 

Pigment Yellow 138,56300, has the chemical structure 138 with X = C1 [4], The synthesis of halogenated compounds (138), for instance P.Y.138, can also be achieved by stepwise heating of tetrachloro phthalic anhydride and 8-amino-chinaldine in molten benzoic acid from 125 to 140 and then to 160°C [5],... 

Regioselectivity in the exchange of formally equal halogens can be found also outside the heterocyclic series. Inductive effects appear to be the controlling factor. For example, 3,3, 5-tribromodibenzyl ether (l,3-dibromo-5-[(3-bromophenyhnethoxy)methyl]benzene 5) is exclusively converted into 3-bromo-5-[(3-bromophenylmethoxy)methyl]benzoic acid (equation 3) when treated consecutively with butyUithium in tetrahydrofuran at —75 °C and dry ice. 

---