bromine

Summary

Summary: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.

Top Publications

  1. Rasolofonjatovo E, Provot O, Hamze A, Bignon J, Thoret S, Brion J, et al. Regioselective hydrostannation of diarylalkynes directed by a labile ortho bromine atom: an easy access to stereodefined triarylolefins, hybrids of combretastatin A-4 and isocombretastatin A-4. Eur J Med Chem. 2010;45:3617-26 pubmed publisher
    ..The cooperative ortho-effect of a labile bromine atom in the regioselective hydrostannation of unsymmetrical diarylalkynes leading to stereodefined triarylolefins ..
  2. Waldmann C, Schober O, Haufe G, Kopka K. A closer look at the bromine-lithium exchange with tert-butyllithium in an aryl sulfonamide synthesis. Org Lett. 2013;15:2954-7 pubmed publisher
    ..A key step is the well-known bromine-lithium exchange reaction of an aryl bromide with tert-butyllithium (t-BuLi)...
  3. Riley K, Murray J, Fanfrlík J, Rezac J, Solá R, Concha M, et al. Halogen bond tunability I: the effects of aromatic fluorine substitution on the strengths of halogen-bonding interactions involving chlorine, bromine, and iodine. J Mol Model. 2011;17:3309-18 pubmed publisher
    ..It is also shown that aromatic fluorine substitutions affect the optimal geometries of the halogen-bonded complexes, often as the result of secondary interactions...
  4. Cuyckens F, Balcaen L, De Wolf K, De Samber B, Van Looveren C, Hurkmans R, et al. Use of the bromine isotope ratio in HPLC-ICP-MS and HPLC-ESI-MS analysis of a new drug in development. Anal Bioanal Chem. 2008;390:1717-29 pubmed publisher
    ..R207910 contains one bromine atom, allowing the detection by ICP-MS...
  5. Kippo T, Hamaoka K, Ryu I. Bromine radical-mediated sequential radical rearrangement and addition reaction of alkylidenecyclopropanes. J Am Chem Soc. 2013;135:632-5 pubmed publisher
    b>Bromine radical-mediated cyclopropylcarbinyl-homoallyl rearrangement of alkylidenecyclopropanes was effectively accomplished by C-C bond formation with allylic bromides, which led to the syntheses of 2-bromo-1,6-dienes...
  6. Romarís Hortas V, Moreda Piñeiro A, Bermejo Barrera P. Microwave assisted extraction of iodine and bromine from edible seaweed for inductively coupled plasma-mass spectrometry determination. Talanta. 2009;79:947-52 pubmed publisher
    ..of edible seaweed samples by tetramethylammonium hydroxide (TMAH) has been investigated to extract iodine and bromine. Inductively coupled plasma-mass spectrometry (ICP-MS) has been used as a multi-element detector...
  7. Allen J, McClean M, Stapleton H, Webster T. Linking PBDEs in house dust to consumer products using X-ray fluorescence. Environ Sci Technol. 2008;42:4222-8 pubmed
    ..We used a portable X-rayfluorescence (XRF) analyzer to nondestructively quantify bromine concentrations in consumer goods...
  8. Ito T, Ishikawa E, Matsuda Y, Tanoue A, Fujimoto M, Matsuo H, et al. Elevated serum levels of bromine do not always indicate pseudohyperchloremia. Clin Exp Nephrol. 2010;14:431-5 pubmed publisher
    ..Hyperchloremia is known to be able to reveal existing bromism, but the fact that bromine (Br(-)) influences chloride (Cl(-)) in assays that use ion electrode machines is not widely known.
  9. Wan Y, Jones P, Wiseman S, Chang H, Chorney D, Kannan K, et al. Contribution of synthetic and naturally occurring organobromine compounds to bromine mass in marine organisms. Environ Sci Technol. 2010;44:6068-73 pubmed publisher
    ..An extraction, separation, and purification method was developed for the identification and quantification of total bromine (TBr), extractable organobromine (EOBr), and five classes of identified EOBrs...

More Information

Publications62

  1. Behrens S, Lösekann T, Pett Ridge J, Weber P, Ng W, Stevenson B, et al. Linking microbial phylogeny to metabolic activity at the single-cell level by using enhanced element labeling-catalyzed reporter deposition fluorescence in situ hybridization (EL-FISH) and NanoSIMS. Appl Environ Microbiol. 2008;74:3143-50 pubmed publisher
    ..Fluorine or bromine atoms were introduced into cells via 16S rRNA-targeted probes, which enabled phylogenetic identification of ..
  2. Zhu P, Chen Y, Wang L, Qian G, Zhou M, Zhou J. A new technology for separation and recovery of materials from waste printed circuit boards by dissolving bromine epoxy resins using ionic liquid. J Hazard Mater. 2012;239-240:270-8 pubmed publisher
    ..Thermal analyses combined with infrared ray spectra (IR) observed that the solid residues were bromine epoxy resins...
  3. Barrett K, Miller S. Enantioselective synthesis of atropisomeric benzamides through peptide-catalyzed bromination. J Am Chem Soc. 2013;135:2963-6 pubmed publisher
    ..Finally, the products of these reactions may be subjected to regioselective metal-halogen exchange and trapping with I(2), setting the stage for utility...
  4. Hua G, Reckhow D. Evaluation of bromine substitution factors of DBPs during chlorination and chloramination. Water Res. 2012;46:4208-16 pubmed publisher
    b>Bromine substitution factor (BSF) was used to quantify the effects of disinfectant dose, reaction time, pH, and temperature on the bromine substitution of disinfection byproducts (DBPs) during chlorination and chloramination...
  5. Küpper F, Carpenter L, Leblanc C, Toyama C, Uchida Y, Maskrey B, et al. In vivo speciation studies and antioxidant properties of bromine in Laminaria digitata reinforce the significance of iodine accumulation for kelps. J Exp Bot. 2013;64:2653-64 pubmed publisher
    The metabolism of bromine in marine brown algae remains poorly understood...
  6. McCall A, Cummings C, Bhave G, Vanacore R, Page McCaw A, Hudson B. Bromine is an essential trace element for assembly of collagen IV scaffolds in tissue development and architecture. Cell. 2014;157:1380-92 pubmed publisher
    b>Bromine is ubiquitously present in animals as ionic bromide (Br(-)) yet has no known essential function...
  7. Gustafson J, Lim D, Miller S. Dynamic kinetic resolution of biaryl atropisomers via peptide-catalyzed asymmetric bromination. Science. 2010;328:1251-5 pubmed publisher
    ..A mechanistic model is advanced that accounts for the basis of selectivity observed...
  8. Yang M, Xu Y, Wang J. Lab-on-valve system integrating a chemiluminescent entity and in situ generation of nascent bromine as oxidant for chemiluminescent determination of tetracycline. Anal Chem. 2006;78:5900-5 pubmed
    ..immobilized microcolumn was incorporated in one port of the LOV for in situ oxidation of KBr and generation of bromine as oxidant for the bromine-hydrogen peroxide-tetracycline (TC) chemiluminescent reaction...
  9. Feiters M, Leblanc C, Küpper F, Meyer Klaucke W, Michel G, Potin P. Bromine is an endogenous component of a vanadium bromoperoxidase. J Am Chem Soc. 2005;127:15340-1 pubmed
  10. Li M, Kinzer J. Structural analysis of oligosaccharides by a combination of electrospray mass spectrometry and bromine isotope tagging of reducing-end sugars with 2-amino-5-bromopyridine. Rapid Commun Mass Spectrom. 2003;17:1462-6 pubmed
    ..model oligosaccharides was revealed with little ambiguity via the diagnostic unique twin peaks arising from the bromine isotopes, for both the molecular ions of the derivatized oligosaccharides and their fragments...
  11. Rose M, Miller P, Baxter M, Appleton G, Crews H, Croasdale M. Bromine and iodine in 1997 UK total diet study samples. J Environ Monit. 2001;3:361-5 pubmed
    Concentrations of bromine and iodine were analysed in samples from the 1997 UK Total Diet Study (TDS) using ICP-MS. The data has been used to estimate dietary exposures of UK consumers to these elements from the typical UK diet...
  12. Choi J, Park H, Jung H, Chung H, Jung J, Choi W. A cyclohexanonyl bromophenol from the red alga Symphyocladia latiuscula. J Nat Prod. 2000;63:1705-6 pubmed
    ..The bromophenol was found to be a scavenger of 1,1-diphenyl-2-picrylhydrazyl radical...
  13. Burns M, Linden C. Another hot tub hazard. Toxicity secondary to bromine and hydrobromic acid exposure. Chest. 1997;111:816-9 pubmed
    ..Additional findings were present and suggested that exposure to a corrosive agent was responsible. Bromine and hydrobromic acid generated from a widely used water disinfectant were implicated as the underlying cause...
  14. Ellis K, Wong W. Human hydrometry: comparison of multifrequency bioelectrical impedance with 2H2O and bromine dilution. J Appl Physiol (1985). 1998;85:1056-62 pubmed
    ..We used multifrequency bioelectrical impedance spectroscopy (BIS), 2H2O dilution, and bromine dilution to assess TBW, ECW, and ICW in 469 healthy subjects (248 males, 221 females) aged 3-29 yr...
  15. Raimondi M, Cascioferro S, Schillaci D, Petruso S. Synthesis and antimicrobial activity of new bromine-rich pyrrole derivatives related to monodeoxypyoluteorin. Eur J Med Chem. 2006;41:1439-45 pubmed
    ..The insertion of a keto or methylene spacer between the phenol group and the pyrroloyl moiety of brominated 2-(2'-hydroxybenzoyl)pyrroles leads to a decrease of the antibacterial activity...
  16. Krow G, Lee Y, Lester W, Liu N, Yuan J, Duo J, et al. 2-Azabicyclo[2.1.1]hexanes. 2. Substitutent effects on the bromine-mediated rearrangement of 2-azabicyclo[2.2.0]hex-5-enes. J Org Chem. 2001;66:1805-10 pubmed
    ..2.0]hexenes 6c-e from 2-methyl- and 2-phenyl-1,2-dihydropyridines 5c-e. Products formed upon addition of bromine to 3-endo-, 4-, and 5-methyl- and 3-endo-phenyl-substituted N-(ethoxycarbonyl)-2-azabicyclo[2.2...
  17. Westerhoff P, Chao P, Mash H. Reactivity of natural organic matter with aqueous chlorine and bromine. Water Res. 2004;38:1502-13 pubmed
    While both aqueous bromine (HOBr/OBr(-)) and chlorine (HOCl/OCl(-)) react with natural organic matter (NOM) during water treatment, limited direct parallel comparison of bromine versus chlorine has been conducted...
  18. Lammel G, Röhrl A, Schreiber H. Atmospheric lead and bromine in Germany: post-abatement levels, variabilities and trends. Environ Sci Pollut Res Int. 2002;9:397-404 pubmed
    Abatement measures since the 1970s have depleted lead and bromine levels in the atmosphere over large parts of Europe...
  19. Fujii R, Yoshida H, Fukusumi S, Habata Y, Hosoya M, Kawamata Y, et al. Identification of a neuropeptide modified with bromine as an endogenous ligand for GPR7. J Biol Chem. 2002;277:34010-6 pubmed
    ..the purified endogenous ligand was a peptide with 29 amino acid residues and that it was uniquely modified with bromine. We subsequently determined that the C-6 position of the indole moiety in the N-terminal Trp was brominated...
  20. Yang X, Peng J, Chen B, Guo W, Liang Y, Liu W, et al. Effects of ozone and ozone/peroxide pretreatments on disinfection byproduct formation during subsequent chlorination and chloramination. J Hazard Mater. 2012;239-240:348-54 pubmed publisher
    ..These results suggest that O3 or O3/H2O2 pretreatments may provide some benefits for the chloramination process in controlling regulated and emerging DBPs in waters without high bromide content...
  21. Demir A, Emrullahoglu M, Pirkin E, Akca N. Darzens reaction of acyl phosphonates with alpha-bromo ketones: selective synthesis of cis- and trans-epoxyphosphonates. J Org Chem. 2008;73:8992-7 pubmed publisher
    ..Changing the base from Cs2CO3 to DBU changed the diastereomeric ratio (trans/cis) from 3/2 to 9/1. Moreover, the treatment of the trans isomer with DBU showed a complete conversion to the corresponding cis isomer...
  22. Gómez J, Gimeno M, Auqué L, Acero P. Characterisation and modelling of mixing processes in groundwaters of a potential geological repository for nuclear wastes in crystalline rocks of Sweden. Sci Total Environ. 2014;468-469:791-803 pubmed publisher
  23. Gatti M, Drinkel E, Wu L, Pusterla I, Gaggia F, Dorta R. Efficient ring-closing metathesis of alkenyl bromides: the importance of protecting the catalyst during the olefin approach. J Am Chem Soc. 2010;132:15179-81 pubmed publisher
    ..Efficient catalysis employing commercially available Grubbs II catalyst is possible through appropriate modification of the starting bromoalkene moiety...
  24. Inuki S, Oishi S, Fujii N, Ohno H. Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group. Org Lett. 2008;10:5239-42 pubmed publisher
    ..With this biscyclization as the key step, total synthesis of (+/-)-lysergic acid, (+/-)-lysergol, and (+/-)-isolysergol was achieved...
  25. Pathak T, Miller S. Site-selective bromination of vancomycin. J Am Chem Soc. 2012;134:6120-3 pubmed publisher
    ..Alternative site selectivity is observed as a function of solvent and replacement of the peptide with guanidine...
  26. Hossaini Z, Rostami Charati F, Soltani S, Mirzaei A, Berijani K. Multicomponent reactions of ammonium thiocyanate, acyl chlorides, alkyl bromides, and enaminones: a facile one-pot synthesis of thiophenes. Mol Divers. 2011;15:911-6 pubmed publisher
    ..The mild reaction conditions and high yields of the products exhibit the good synthetic advantage of these methods...
  27. Yu W, Li P, Xu F, Hu J, Zhang Q, Wang W. Quantum chemical and direct dynamic study on homogeneous gas-phase formation of PBDD/Fs from 2,4,5-tribromophenol and 3,4-dibromophenol. Chemosphere. 2013;93:512-20 pubmed publisher
    ..The present study shows that the formation of PBDDs dominates over the formation of PBDFs. The meta bromine facilitates the dimerization of bromophenoxy radicals (BPRs), whereas the para and ortho bromines suppress the ..
  28. Barrett K, Metrano A, Rablen P, Miller S. Spontaneous transfer of chirality in an atropisomerically enriched two-axis system. Nature. 2014;509:71-5 pubmed publisher
    ..The stereodynamics of these substrates provides an opportunity to observe a curious interplay of kinetics and thermodynamics intrinsic to a system of stereoisomers that is constrained to a situation of partial equilibrium...
  29. Heyda J, Hrobárik T, Jungwirth P. Ion-specific interactions between halides and basic amino acids in water. J Phys Chem A. 2009;113:1969-75 pubmed publisher
    ..Because interactions of halides with positively charged groups exhibit a local character and are not overwhelmingly strong, similar behavior will be observed (in an additive sense) as well at surfaces of hydrated proteins...
  30. Mukherjee C, Weyhermüller T, Bothe E, Chaudhuri P. Oxidation of an o-iminobenzosemiquinone radical ligand by molecular bromine: structural, spectroscopic, and reactivity studies of a copper(II) o-iminobenzoquinone complex. Inorg Chem. 2008;47:2740-6 pubmed publisher
    ..oxidation of the noninnocent ligand 2-anilino-4,6-di- tert-butylphenol, H2L, is readily oxidized by molecular bromine to a bis(o-iminobenzoquinone)copper(II) complex, 2...
  31. Parsons T, Ghellamallah C, Male L, Spencer N, Grainger R. Regioselective dibromination of methyl indole-3-carboxylate and application in the synthesis of 5,6-dibromoindoles. Org Biomol Chem. 2011;9:5021-3 pubmed publisher
    Treatment of methyl indole-3-carboxylate with bromine in acetic acid gives methyl 5,6-dibromoindole-3-carboxylate regioselectively, from which the parent 5,6-dibromoindole can be accessed via a one-pot, microwave-mediated ester ..
  32. Ceres G, Conte V, Mirruzzo V, Kolar J, Strlic M. Imidazolium-based ionic liquids for the efficient treatment of iron gall inked papers. ChemSusChem. 2008;1:921-6 pubmed publisher
    ..Furthermore, it does not lead to the yellowing of paper nor does it significantly affect the colour of the ink...
  33. Peng C. Prediction of retention indices. VI: Isothermal and temperature-programmed retention indices, methylene value, functionality constant, electronic and steric effects. J Chromatogr A. 2010;1217:3683-94 pubmed publisher
    ..Examples of the influence of molecular electronic effects and steric effects on retention index are given and discussed...
  34. MCFARLAND E. Chemistry. Unconventional chemistry for unconventional natural gas. Science. 2012;338:340-2 pubmed publisher
  35. Yamagishi M, Okazaki J, Nishigai K, Hata T, Urabe H. Additive-free nucleophilic addition of imidazolines and imidazoles to haloacetylenes. Org Lett. 2012;14:34-7 pubmed publisher
    ..These reaction conditions are also valid for the similar addition of imidazoles...
  36. Serra A, Pineiro M, Rocha Gonsalves A, Abrantes M, Laranjo M, Santos A, et al. Halogen atom effect on photophysical and photodynamic characteristics of derivatives of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin. J Photochem Photobiol B. 2008;92:59-65 pubmed publisher
    ..5,10,15,20-Tetrakis(2-bromo-5-hydroxyphenyl)porphyrin showed the best cytotoxicity with values of IC(50) of 113 nM over WiDr cells and 52nM over A375 cells...
  37. Rogers J, Price J, Wendling M, Perry M, Reid F, Kiser R, et al. An assessment of transcriptional changes in porcine skin exposed to bromine vapor. J Biochem Mol Toxicol. 2011;25:252-62 pubmed publisher
    b>Bromine is an industrial chemical that can cause severe cutaneous burns. This study was a preliminary investigation into the effect of cutaneous exposure to bromine vapor using a weanling swine burn model and microarray analysis...
  38. Tupper J, Stratford M, Hill S, Tozer G, Dachs G. In vivo characterization of horseradish peroxidase with indole-3-acetic acid and 5-bromoindole-3-acetic acid for gene therapy of cancer. Cancer Gene Ther. 2010;17:420-8 pubmed publisher
    ..Treatment response could not be improved using different drug scheduling or drug vehicle, nor by combining HRP-directed gene therapy with fractionated radiotherapy...
  39. Flynn M. Analysis of exposure biomarker relationships with the Johnson SBB distribution. Ann Occup Hyg. 2007;51:533-41 pubmed
    ..A comparison with the usual two-parameter log-normal approach shows that in some cases the S(BB) distribution may offer advantages...
  40. Lei M, Wang N, Zhu L, Tang H. Peculiar and rapid photocatalytic degradation of tetrabromodiphenyl ethers over Ag/TiO2 induced by interaction between silver nanoparticles and bromine atoms in the target. Chemosphere. 2016;150:536-544 pubmed publisher
    ..Ag(0) exerted affinity interaction with bromine atoms, and the storing of electrons on Ag(0) increased the binding interaction, which elongated the C-Br bond of ..
  41. Bissember A, Levina A, Fu G. A mild, palladium-catalyzed method for the dehydrohalogenation of alkyl bromides: synthetic and mechanistic studies. J Am Chem Soc. 2012;134:14232-7 pubmed publisher
  42. Chiang W, Chen P, Nien P, Ho K. Amperometric detection of cholesterol using an indirect electrochemical oxidation method. Steroids. 2011;76:1535-40 pubmed publisher
    The indirect electrochemical oxidation method using bromine species in an organic media for measuring cholesterol was developed. The electrochemical behaviors of cholesterol were examined by cyclic voltammetry in a potential range of -0...
  43. Hermanson M, Isaksson E, Forsström S, Teixeira C, Muir D, Pohjola V, et al. Deposition history of brominated flame retardant compounds in an ice core from Holtedahlfonna, Svalbard, Norway. Environ Sci Technol. 2010;44:7405-10 pubmed publisher
    ..Average air mass trajectories over 10 years show >75% of atmospheric flow to Holtedahlfonna coming from Eurasia during haze periods (March and April)...
  44. Stuart H, Ibarra C, Abdallah M, Boon R, Neels H, Covaci A. Concentrations of brominated flame retardants in dust from United Kingdom cars, homes, and offices: causes of variability and implications for human exposure. Environ Int. 2008;34:1170-5 pubmed publisher
    ..Significant negative correlation was observed in one room between concentrations of BDE-47, 99, and 153 and dust loading (g dust m(-2) floor), suggesting "dilution" occurs at higher dust loadings...
  45. Fu Y, Chen J, Xu H, Van Oosterwijck C, Zhang X, Dehaen W, et al. Fully-branched hyperbranched polymers with a diselenide core as glutathione peroxidase mimics. Macromol Rapid Commun. 2012;33:798-804 pubmed publisher
    ..The obtained polymer has demonstrated prominent GPx activity as desired, which could be attributed to the hydrophobic, densely branched and core-shell structure of the polymer surrounding the catalytic center...
  46. Wager K, Daniels M. Palladium-catalyzed cross-coupling of benzyl thioacetates and aryl halides. Org Lett. 2011;13:4052-5 pubmed publisher
    ..A one-pot protocol for forming benzyl aryl thioethers from a benzyl halide, potassium thioacetate, and an aryl bromide has also been demonstrated...
  47. Turina A, Quinteros G, Caruso B, Moyano E, Perillo M. Surface active benzodiazepine-bromo-alkyl conjugate for potential GABAA-receptor purification. Org Biomol Chem. 2011;9:5737-47 pubmed publisher
    ..be stabilize though London-type interactions within a phospholipidic coating layer and/or through halogen bonding with an electron-donor surface via its terminal bromine atom while GABA(A)-R might be recognized through the CNZ moiety.
  48. Wishkerman A, Gebhardt S, McRoberts C, Hamilton J, Williams J, Keppler F. Abiotic methyl bromide formation from vegetation, and its strong dependence on temperature. Environ Sci Technol. 2008;42:6837-42 pubmed
    ..Several plant samples with known bromine content, including ash (Fraxinus excelsior), saltwort (Batis maritima), tomato reference material (NIST-1573a), ..
  49. Ferraudi G, Piñero D, Chakraborty I, Raptis R, Lappin A, Berlin N. Mechanistic and energetic aspects of the thermal and photochemical redox chemistry of the octanuclear cubane complexes, Fe(III)(8)(mu(4)-O(4))(mu-pyrazolate)(12)X(4) (X = Cl or Br). J Phys Chem A. 2010;114:5702-9 pubmed publisher
    ..Quantum yields are limited by the rapid recombination of the photofragments. The charge transfer spectroscopy of the products was rationalized on the basis of parameters derived from the thermal electron transfer reactions...
  50. Mosselhi M, Neidlein R. Nucleosides 5(15): synthesis of novel 1,2,4-triazolo[3,4-c]-1,2,4-triazole nucleosides. Nucleosides Nucleotides Nucleic Acids. 2009;28:1095-103 pubmed publisher
    ..Reaction of 5 with aromatic aldehydes yielded the corresponding hydrazones 6, which cyclized under bromination in acetic acid to give 8. Debenzoylation of 8 afforded novel 1,2,4-triazolo[3,4-c]-1,2,4-triazole nucleosides 9...
  51. Martinelli E, Agostini S, Galli G, Chiellini E, Glisenti A, Pettitt M, et al. Nanostructured films of amphiphilic fluorinated block copolymers for fouling release application. Langmuir. 2008;24:13138-47 pubmed publisher
    ..The results are discussed in terms of the changes in surface structure caused by immersion and the effects such changes may have on the adhesion of the test organisms...
  52. Bubbico R, Mazzarotta B. Accidental release of toxic chemicals: influence of the main input parameters on consequence calculation. J Hazard Mater. 2008;151:394-406 pubmed
    ..In particular, the boiling temperature of the chemical has revealed to be the main parameter affecting the type of dependence of the impact distances on the input variables...
  53. Andra S, Makris K, Shine J, Lu C. Co-leaching of brominated compounds and antimony from bottled water. Environ Int. 2012;38:45-53 pubmed publisher
    ..Our focus was on leaching of antimony (Sb) and brominated compounds expressed by total soluble bromine (Br) measurements, including those of polybrominated diphenyl ethers (PBDE)...