halogenated hydrocarbons


Summary: Hydrocarbon compounds with one or more HYDROGEN atoms substituted with HALOGENS.

Top Publications

  1. Meng X, Zeng E, Yu L, Mai B, Luo X, Ran Y. Persistent halogenated hydrocarbons in consumer fish of China: regional and global implications for human exposure. Environ Sci Technol. 2007;41:1821-7 pubmed
    Concentrations of persistent halogenated hydrocarbons (PHHs) were determined in 13 consumer fish species (a total of 390 individuals) collected from a major fish-farming region of China...
  2. Gunnare S, Vidali M, Lillienberg L, Ernstgård L, Sjögren B, Hagberg M, et al. Non-positive autoimmune responses against CYP2E1 in refrigeration mechanics exposed to halogenated hydrocarbons. Sci Total Environ. 2007;383:90-7 pubmed
    ..Serum from 44 Swedish men, occupationally exposed to halogenated hydrocarbons, was screened for antibodies against CYP2E1 with enzyme-linked immunosorbent assay...
  3. Hagmar L, Bjork J, Sjodin A, Bergman A, Erfurth E. Plasma levels of persistent organohalogens and hormone levels in adult male humans. Arch Environ Health. 2001;56:138-43 pubmed
    ..High consumption of organohalogen-polluted fish did not appear to affect plasma concentrations of pituitary, thyroid, or testosterone hormone levels in male adults. ..
  4. Kasai A, Hiramatsu N, Meng Y, Yao J, Maeda S, Kitamura M. Fast-track DRESSA: a bioassay for fast, sensitive, and selective detection of halogenated and polycyclic aromatic hydrocarbons. Anal Biochem. 2005;337:84-8 pubmed
    ..Because of its time-saving property and easiness, sensitiveness, and specificity, the fast-track DRESSA would be advantageous for high-throughput screening of dioxin and dioxin-like compounds in environmental samples. ..
  5. Kirkegaard M, Sonne C, Leifsson P, Dietz R, Born E, Muir D, et al. Histology of selected immunological organs in polar bear (Ursus maritimus) from East Greenland in relation to concentrations of organohalogen contaminants. Sci Total Environ. 2005;341:119-32 pubmed
  6. Brown Woodman P, Hayes L, Huq F, Herlihy C, Picker K, Webster W. In vitro assessment of the effect of halogenated hydrocarbons: chloroform, dichloromethane, and dibromoethane on embryonic development of the rat. Teratology. 1998;57:321-33 pubmed
    b>Halogenated hydrocarbons are widely used in industry, the laboratory, and in the home...
  7. Zhang Z, Huang J, Ma B, Kishi Y. Further improvement on sulfonamide-based ligand for catalytic asymmetric 2-haloallylation and allylation. Org Lett. 2008;10:3073-6 pubmed publisher
    ..The new ligand has an appealing advantage over the first generation ligand; its high crystallinity allows effective recovery of the ligand from a reaction in a pure form. ..
  8. Schultz I, Reed S, Pratt A, Skillman A. Quantitative oral dosing of water soluble and lipophilic contaminants in the Japanese medaka (Oryzias latipes). Comp Biochem Physiol C Toxicol Pharmacol. 2007;145:86-95 pubmed
    ..3-3 h depending on HAA. PBDE-47 was more slowly absorbed with peak levels occurring by 18 h and very slowly eliminated with an elimination half-life of 281 h. ..
  9. Cahiez G, Habiak V, Duplais C, Moyeux A. Iron-catalyzed alkylations of aromatic grignard reagents. Angew Chem Int Ed Engl. 2007;46:4364-6 pubmed

Scientific Experts

More Information


  1. Lee L, Kreutter K, Pan W, Crysler C, Spurlino J, Player M, et al. 2-(2-Chloro-6-fluorophenyl)acetamides as potent thrombin inhibitors. Bioorg Med Chem Lett. 2007;17:6266-9 pubmed
    ..The aminopyridine P1s also provided an increase in potency. ..
  2. Ko C, Hsung R, Al Rashid Z, Feltenberger J, Lu T, Yang J, et al. A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers. Org Lett. 2007;9:4459-62 pubmed
    ..A stereoselective halo-etherification of chiral enamides is described here. This work provides an approach to halogen containing cyclic ethers and reveals further mechanistic insights to the chemistry of chiral enamides. ..
  3. Molander G, Fumagalli T. Palladium(0)-catalyzed suzuki-miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides. J Org Chem. 2006;71:5743-7 pubmed
    ..When stereodefined alkenyl bromides are employed, the resulting styrene derivatives are accessed stereospecifically. A variety of functional groups are tolerated in both coupling partners. ..
  4. Bonasoni P, Laj P, Angelini F, Arduini J, Bonafè U, Calzolari F, et al. The ABC-Pyramid Atmospheric Research Observatory in Himalaya for aerosol, ozone and halocarbon measurements. Sci Total Environ. 2008;391:252-61 pubmed
    ..With the name of "Nepal Climate Observatory-Pyramid" the station is now part of the Observatory program of the ABC project. ..
  5. Viel C, Labrude P. [Maurice Meslans (1862-1938), pharmacist student of Henri Moissan]. Rev Hist Pharm (Paris). 2008;55:473-84 pubmed
    ..After a short biography, the authors analyse the scientific work of Maurice Meslans, pharmacist and chemist, Henri Moissan's advanced student, pioneer of organofluorocompounds chemistry. ..
  6. Bengtson Nash S, Poulsen A, Kawaguchi S, Vetter W, Schlabach M. Persistent organohalogen contaminant burdens in Antarctic krill (Euphausia superba) from the eastern Antarctic sector: a baseline study. Sci Total Environ. 2008;407:304-14 pubmed publisher
  7. Moncomble A, le Floch P, Gosmini C. Cobalt-catalyzed formation of symmetrical biaryls and its mechanism. Chemistry. 2009;15:4770-4 pubmed publisher
    ..Preliminary DFT calculations have shown that the involvement of a Co(I)/Co(III) couple is realistic at least in the case of 1,3-diazadienes as ligands (FG = functional group). ..
  8. Kull T, Cabrera J, Peters R. Catalytic asymmetric synthesis of trans-configured beta-lactones: cooperation of Lewis acid and ion pair catalysis. Chemistry. 2010;16:9132-9 pubmed publisher
    ..The utility was further demonstrated by nucleophilic ring-opening reactions that provide highly enantiomerically enriched anti-aldol products. ..
  9. Anderson K, Buchwald S. General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water. Angew Chem Int Ed Engl. 2005;44:6173-7 pubmed
  10. Miltner R, Speth T, Richardson S, Krasner S, Weinberg H, Simmons J. Integrated disinfection by-products mixtures research: disinfection of drinking waters by chlorination and ozonation/postchlorination treatment scenarios. J Toxicol Environ Health A. 2008;71:1133-48 pubmed publisher
  11. Inés B, Moreno I, Sanmartin R, Domínguez E. A nonsymmetric pincer-catalyzed Suzuki-Miyaura arylation of benzyl halides and other nonactivated unusual coupling partners. J Org Chem. 2008;73:8448-51 pubmed publisher
    ..Most of the reported reactions are achieved in aqueous media, with all of the advantages implied. ..
  12. Surdo E, Cussler E, Novak P, Arnold W. Geomembranes containing powdered activated carbon have the potential to improve containment of chlorinated aromatic contaminants. Environ Sci Technol. 2009;43:8916-22 pubmed publisher
    ..This flux reduction was achieved with less than a third of the carbon used in the HDPE case, an improvement that is likely the result of better solute uptake in the hydrophilic PVA layer. ..
  13. Sayavedra Soto L, Gvakharia B, Bottomley P, Arp D, Dolan M. Nitrification and degradation of halogenated hydrocarbons--a tenuous balance for ammonia-oxidizing bacteria. Appl Microbiol Biotechnol. 2010;86:435-44 pubmed publisher
    ..These and other biosensors may help to preserve the tenuous balance that exists when nitrification occurs in waste streams containing alternative AOB substrates such as halogenated hydrocarbons.
  14. Mangas Sánchez J, Busto E, Gotor Fernández V, Gotor V. Straightforward synthesis of enantiopure 2,3-dihydrobenzofurans by a sequential stereoselective biotransformation and chemical intramolecular cyclization. Org Lett. 2010;12:3498-501 pubmed publisher
    ..These novel compounds have been prepared in enantiopure form and in good overall yield through a straightforward route. ..
  15. Douvas M, Hogan K, Ji Y, Hollenback D, Bonham L, Singer J, et al. Effect of lysophosphatidic acid acyltransferase-beta inhibition in acute leukemia. Leuk Res. 2006;30:1027-36 pubmed
    ..These data suggest that CT-32228 may have potential in the treatment of acute leukemias, but that efficacy is more directly related to the degree of cell proliferation rather than to the level of LPAAT-beta expression or activity. ..
  16. Tsydenova O, Sudaryanto A, Kajiwara N, Kunisue T, Batoev V, Tanabe S. Organohalogen compounds in human breast milk from Republic of Buryatia, Russia. Environ Pollut. 2007;146:225-32 pubmed
    ..Although high EDIs raise concern for possible toxic effects of OCs, women in Buryatia are recommended to breastfeed due to numerous advantages of breastfeeding for mother and child. ..
  17. Stiefelhagen P. [Pimples and pustules have various causes. Acne reveals the muscle builder]. MMW Fortschr Med. 2006;148:14-5 pubmed
  18. Mann M, Mkwananzi H, Antunes E, Whibley C, Hendricks D, Bolton J, et al. Halogenated monoterpene aldehydes from the South African marine alga Plocamium corallorhiza. J Nat Prod. 2007;70:596-9 pubmed
    ..The structures of the new compounds were determined by interpretation of their spectroscopic data and synthesis and mass spectrometric analysis of their pentafluorobenzyloxime (PFBO) derivatives...
  19. Su Y, Zhu Y. Transport mechanisms for the uptake of organic compounds by rice (Oryza sativa) roots. Environ Pollut. 2007;148:94-100 pubmed
    ..For LIN and TCB, apoplastic transport pathway plays major roles in the first 2h of uptake, then symplastic transport pathway dominates uptake. ..
  20. Miller B, Weiss R, Salameh P, Tanhua T, Greally B, Mühle J, et al. Medusa: a sample preconcentration and GC/MS detector system for in situ measurements of atmospheric trace halocarbons, hydrocarbons, and sulfur compounds. Anal Chem. 2008;80:1536-45 pubmed publisher
  21. Waldo J, Zhang X, Shi F, Larock R. Efficient synthesis of fluoren-9-ones by the palladium-catalyzed annulation of arynes by 2-haloarenecarboxaldehydes. J Org Chem. 2008;73:6679-85 pubmed publisher
    ..Fluoren-9-ones and derivatives are readily prepared in good yields by the annulation of in situ generated arynes by 2-haloarenecarboxaldehydes in the presence of a palladium catalyst. ..
  22. Bentzen T, Muir D, Amstrup S, O Hara T. Organohalogen concentrations in blood and adipose tissue of Southern Beaufort Sea polar bears. Sci Total Environ. 2008;406:352-67 pubmed publisher
    ..Although correlation between OHC concentrations in blood and adipose tissue was examined, the predictability of concentrations in one matrix for the other was limited. ..
  23. Fillion E, Wilsily A, Fishlock D. Probing persistent intramolecular C-H...X (X = O, S, Br, Cl, and F) bonding in solution using benzyl Meldrum's acid derivatives. J Org Chem. 2009;74:1259-67 pubmed publisher
    ..Further understanding of intramolecular C-H...X bonds was gained by characterization of benzyl Meldrum's acids in the solid state, by X-ray analysis, and by the conformation correlated to the observations made in solution. ..
  24. Fabjan E, Hulzebos E. An evaluation of selected valid and mechanistically based SARs for skin sensitisation. Toxicol In Vitro. 2008;22:468-90 pubmed
    ..For substances which fit within the boundaries of the proposed alerts, it is assumed that they would be classified as sensitising in accordance with EU classification and labelling rules. ..
  25. Kalyani D, Dick A, Anani W, Sanford M. A simple catalytic method for the regioselective halogenation of arenes. Org Lett. 2006;8:2523-6 pubmed
    ..These transformations have been applied to a wide array of substrates and can provide products that are complementary to those obtained via conventional electrophilic aromatic substitution reactions. [reaction: see text] ..
  26. Jimenez J, Vansach T, Yoshida W, Sakamoto B, Porzgen P, Horgen F. Halogenated fatty acid amides and cyclic depsipeptides from an eastern Caribbean collection of the cyanobacterium Lyngbya majuscula. J Nat Prod. 2009;72:1573-8 pubmed publisher
    ..Compounds 1-4 and 6 were assessed for general cell toxicity in human embryonic kidney (HEK293) cells. Only itralamide B (4) displayed significant cytotoxicity, showing an IC(50) value of 6 +/- 1 muM. ..
  27. Korivi R, Cheng C. Protecting-group-free total synthesis of isoquinoline alkaloids by nickel-catalyzed annulation of o-halobenzaldimine with an alkyne as the key step. Chemistry. 2010;16:282-7 pubmed publisher
    ..The synthesis requires four steps from o-bromobenzaldehyde derivatives. Transformations of these alkaloids to the other alkaloids in this family are also discussed herein. ..
  28. Billingsley K, Buchwald S. Highly efficient monophosphine-based catalyst for the palladium-catalyzed suzuki-miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters. J Am Chem Soc. 2007;129:3358-66 pubmed
    ..Specific factors that govern the efficacy of the transformation for certain heterocyclic motifs were also investigated. ..
  29. Eggink M, Wijtmans M, Ekkebus R, Lingeman H, De Esch I, Kool J, et al. Development of a selective ESI-MS derivatization reagent: synthesis and optimization for the analysis of aldehydes in biological mixtures. Anal Chem. 2008;80:9042-51 pubmed publisher
    ..Finally, of all aldehydes, pentanal and hexanal were detected at elevated levels in pooled healthy human urine samples. ..
  30. Tiseni P, Peters R. Catalytic asymmetric formation of delta-lactones from unsaturated acyl halides. Chemistry. 2010;16:2503-17 pubmed publisher
    ..In addition, various synthetic transformations of 6-CCl(3)- or 4-silyl-substituted alpha,beta-unsaturated delta-lactones, giving access to a number of valuable delta-lactone building blocks, were investigated. ..
  31. Zhang X, Larock R. Palladium-catalyzed annulation of arynes by 2-halobenzaldehydes: synthesis of fluoren-9-ones. Org Lett. 2005;7:3973-6 pubmed
    ..reaction: see text] ..
  32. Dohi T, Morimoto K, Maruyama A, Kita Y. Direct synthesis of bipyrroles using phenyliodine bis(trifluoroacetate) with bromotrimethylsilane. Org Lett. 2006;8:2007-10 pubmed
    ..This straightforward synthesis could provide 2,3'-bipyrrole by the choice of a N-substituent of pyrrole. Mechanistic consideration of the present reaction is also described. ..
  33. Cimino P, Pavone M, Barone V. Halogen bonds between 2,2,6,6-tetramethylpiperidine-N-oxyl radical and CxHyFzI species: DFT calculations of physicochemical properties and comparison with hydrogen bonded adducts. J Phys Chem A. 2007;111:8482-90 pubmed
  34. Giwercman A, Rylander L, Rignell Hydbom A, Jonsson B, Pedersen H, Ludwicki J, et al. Androgen receptor gene CAG repeat length as a modifier of the association between persistent organohalogen pollutant exposure markers and semen characteristics. Pharmacogenet Genomics. 2007;17:391-401 pubmed
    ..Other studies regarding this matter are warranted. ..
  35. Polkowska Z, Kozłowska K, Mazerska Z, Gorecki T, Namiesnik J. Volatile organohalogen compounds in human urine: the effect of environmental exposure. Chemosphere. 2006;62:626-40 pubmed
    ..VOX levels in the urine of subjects not exposed to them in the workplace were significantly lower. Their presence in the organisms was most probably related to consumption of tap water produced by chlorination of surface waters. ..
  36. Viña D, Del Olmo E, López Pérez J, San Feliciano A. Regioselective synthesis of 1-alkyl- or 1-aryl-1H-indazoles via copper-catalyzed cyclizations of 2-haloarylcarbonylic compounds. Org Lett. 2007;9:525-8 pubmed
    ..Ligands commonly employed as catalysts for intermolecular amination were shown to be ineffective for this cyclization. ..
  37. Giwercman A, Rignell Hydbom A, Toft G, Rylander L, Hagmar L, Lindh C, et al. Reproductive hormone levels in men exposed to persistent organohalogen pollutants: a study of inuit and three European cohorts. Environ Health Perspect. 2006;114:1348-53 pubmed
    ..90 nmol/L; 95% CI, -0.04 to 1.9 nmol/L). Gonadotropin levels and SHBG seem to be affected by POP exposure, but the pattern of endocrine response is the subject of considerable geographic variation. ..
  38. Kucklick J, Schantz M, Pugh R, Porter B, Poster D, Becker P, et al. Marine mammal blubber reference and control materials for use in the determination of halogenated organic compounds and fatty acids. Anal Bioanal Chem. 2010;397:423-32 pubmed publisher
  39. Zhang X, Larock R. Synthesis of spiro[4.5]trienones by intramolecular ipso-halocyclization of 4-(p-methoxyaryl)-1-alkynes. J Am Chem Soc. 2005;127:12230-1 pubmed
    ..ICl, I2, and Br2 are all effective electrophiles for this process under carefully optimized reaction conditions. ..
  40. Zhu L, Cheng L, Zhang Y, Xie R, You J. Highly efficient copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides. J Org Chem. 2007;72:2737-43 pubmed
    ..The protocol could also be applicable to other pi-electron-rich nitrogen heterocycles (pyrrole, pyrazole, indole, benzimidazole, and triazole), affording the N-arylazoles in good to excellent yields. ..
  41. Wichard T, Pohnert G. Formation of halogenated medium chain hydrocarbons by a lipoxygenase/hydroperoxide halolyase-mediated transformation in planktonic microalgae. J Am Chem Soc. 2006;128:7114-5 pubmed
    ..This adds a fundamentally new pathway to the limited set of halogenating enzymatic activities known from nature. ..
  42. Morales Suarez Varela M, Olsen J, Johansen P, Kaerlev L, Guénel P, Arveux P, et al. Occupational exposures and mycosis fungoides. A European multicentre case-control study (Europe). Cancer Causes Control. 2005;16:1253-9 pubmed
    ..The JEM included aromatic and/or halogenated hydrocarbons (AAHs), chrome (VI) and its salts, electromagnetic radiations, silica and pesticides...
  43. Takigami H, Suzuki G, Hirai Y, Sakai S. Brominated flame retardants and other polyhalogenated compounds in indoor air and dust from two houses in Japan. Chemosphere. 2009;76:270-7 pubmed publisher
    ..Furthermore, a preliminary estimation was made of the likely magnitude of inhabitants' exposure to PHCs via inhalation and dust ingestion in the two houses. ..
  44. Qu G, Mao Z, Niu H, Wang D, Xia C, Guo H. Straightforward and highly efficient catalyst-free one-step synthesis of 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates, and 6-methylpurines through S(N)Ar-based reactions of 6-halopurines with ethyl acetoacetate. Org Lett. 2009;11:1745-8 pubmed publisher
    ..No metal catalyst and ligand were required. ..
  45. Malarvannan G, Kunisue T, Isobe T, Sudaryanto A, Takahashi S, Prudente M, et al. Organohalogen compounds in human breast milk from mothers living in Payatas and Malate, the Philippines: levels, accumulation kinetics and infant health risk. Environ Pollut. 2009;157:1924-32 pubmed publisher
    ..A few individuals accumulated CHLs close to or even higher than the tolerable daily intake guidelines proposed by Health Canada. ..
  46. Okazaki T, Laali K. Probing the intermediates of halogen addition to alkynes: bridged halonium versus open halovinyl cation; a theoretical study. J Org Chem. 2005;70:9139-46 pubmed
    ..With the CF3 derivative (when X = F), a formal F shift results in polyfluoroallyl cation generation from fluorovinyl cation as starting geometry. ..
  47. Li J, Ma M, Wang Z. A two-hybrid yeast assay to quantify the effects of xenobiotics on thyroid hormone-mediated gene expression. Environ Toxicol Chem. 2008;27:159-67 pubmed
    ..The results are further evidence of thyroid-related effects of environmentally relevant PHAHs. ..
  48. Baycan N, Thomanetz E, Sengul F. Influence of chloride concentration on the formation of AOX in UV oxidative system. J Hazard Mater. 2007;143:171-6 pubmed
    ..Treatment was followed by TOC and AOX measurements. Approximately 98% and 95% TOC removal efficiencies were obtained for the treatment of acetone and ABS containing wastewaters, respectively. ..
  49. Frische M, Garofalo K, Hansteen T, Borchers R, Harnisch J. The origin of stable halogenated compounds in volcanic gases. Environ Sci Pollut Res Int. 2006;13:406-13 pubmed
    ..Recommendation and Outlook. Our results suggest that the investigated volcanoes do not constitute a significant natural source for CFCs, HFCs, HCFCs, halons, CF4, SF6 and NF3. ..
  50. Mühlebach S, Karlaganis G, Honegger U. Kinetic assessment of persistent halogenated xenobiotics in cell culture models: comparison of mono- and poly-halogenated compounds. Chemosphere. 2006;62:1838-45 pubmed
    ..Well-defined cell culture systems, especially the sectorial model, are appropriate to screen for bioaccumulation and cytotoxicity of (unknown) chemical entities in vitro. ..
  51. Everson D, Shrestha R, Weix D. Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides. J Am Chem Soc. 2010;132:920-1 pubmed publisher
    ..The reaction appears to avoid the formation of intermediate organomanganese species, and a synergistic effect was found when a mixture of two ligands was employed. ..
  52. Evans T. Rapid elimination of field colonies of subterranean termites (Isoptera: Rhinotermitidae) using bistrifluron solid bait pellets. J Econ Entomol. 2010;103:423-32 pubmed
    ..The use of a mound building species demonstrated clearly colony level effects before and after termites stopped foraging in bait stations. ..
  53. Olsman H, Engwall M, Kammann U, Klempt M, Otte J, Bavel B, et al. Relative differences in aryl hydrocarbon receptor-mediated response for 18 polybrominated and mixed halogenated dibenzo-p-dioxins and -furans in cell lines from four different species. Environ Toxicol Chem. 2007;26:2448-54 pubmed
    ..Although the REP factors exhibited species-specific differences, overall resembling rank orders of dioxin-like potency were obtained. ..