4,5-Dibromo-1-methyl-1<i>H</i>-imidazole

Noland, Wayl­and E.; Cole, Kevin P.; Britton, Doyle

doi:10.1107/s1600536803005269

Cited by 3 publications

(4 citation statements)

References 8 publications

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“…Excess HOBr in brominated pools and spas could explain the formation of the trisubstituted imidazole vs mono- and dibrominated isomers. For example, in the synthesis of 4,5-dibromo-1-methyl-1 H -imidazole, the formation of the 2,4,5-tribromo-1-methyl-1 H -imidazole also occurs . Possible sources of imidazole precursors include the amino acid histidine, introduced via urine, and pharmaceuticals and skin-care products containing an imidazole group.…”

Section: Resultsmentioning

confidence: 99%

“…For example, in the synthesis of 4,5dibromo-1-methyl-1H-imidazole, the formation of the 2,4,5tribromo-1-methyl-1H-imidazole also occurs. 67 Possible sources of imidazole precursors include the amino acid histidine, introduced via urine, and pharmaceuticals and skin-care products containing an imidazole group. Some antibiotics, sedatives, and antifungal drugs contain an imidazole group in their structures.…”

Section: Environmental Science and Technologymentioning

confidence: 99%

See 1 more Smart Citation

Progressive Increase in Disinfection Byproducts and Mutagenicity from Source to Tap to Swimming Pool and Spa Water: Impact of Human Inputs

Daiber

DeMarini

Ravuri

et al. 2016

Environ. Sci. Technol.

124

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Pools and spas are enjoyed throughout the world for exercise and relaxation. However, there are no previous studies on mutagenicity of disinfected spa (hot tub) waters or comprehensive identification of disinfection byproducts (DBPs) formed in spas. Using 28 water samples from seven sites, we report the first integrated mutagenicity and comprehensive analytical chemistry of spas treated with chlorine, bromine, or ozone, along with pools treated with these same disinfectants. Gas chromatography (GC) with high-resolution mass spectrometry, membrane-introduction mass spectrometry, and GC-electron capture detection were used to comprehensively identify and quantify DBPs and other contaminants. Mutagenicity was assessed by the Salmonella mutagenicity assay. More than 100 DBPs were identified, including a new class of DBPs, bromoimidazoles. Organic extracts of brominated pool/spa waters were 1.8× more mutagenic than chlorinated ones; spa waters were 1.7× more mutagenic than pools. Pool and spa samples were 2.4 and 4.1× more mutagenic, respectively, than corresponding tap waters. The concentration of the sum of 21 DBPs measured quantitatively increased from finished to tap to pool to spa; and mutagenic potency increased from finished/tap to pools to spas. Mutagenic potencies of samples from a chlorinated site correlated best with brominated haloacetic acid concentrations (Br-HAAs) (r = 0.98) and nitrogen-containing DBPs (N-DBPs) (r = 0.97) and the least with Br-trihalomethanes (r = 0.29) and Br-N-DBPs (r = 0.04). The mutagenic potencies of samples from a brominated site correlated best (r = 0.82) with the concentrations of the nine HAAs, Br-HAAs, and Br-DBPs. Human use increased significantly the DBP concentrations and mutagenic potencies for most pools and spas. These data provide evidence that human precursors can increase mutagenic potencies of pools and spas and that this increase is associated with increased DBP concentrations.

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Section: Resultsmentioning

confidence: 99%

Section: Environmental Science and Technologymentioning

confidence: 99%

Progressive Increase in Disinfection Byproducts and Mutagenicity from Source to Tap to Swimming Pool and Spa Water: Impact of Human Inputs

Daiber

DeMarini

Ravuri

et al. 2016

Environ. Sci. Technol.

124

View full text Add to dashboard Cite

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“…For the structures of various related compounds, see: Delest et al (2008); Poverlein et al (2007); Panday et al (2000); Phillips et al (1997); Terinek & Vasella (2003); Mukai & Nishikawa (2010a,b); Noland et al (2003); Dou & Weiss (1992); Nagatomo et al (1995). For the use of diiodoimidazoles as starting compounds for ligand synthesis, see: Haruki et al (1965); Ito & Uedaira (2004); Kim et al (1999); Zhang et al (2006).…”

Section: Related Literaturementioning

confidence: 98%

4,5-Diiodo-2-phenyl-1H-imidazole

2012

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The structure of the title compound, C9H6I2N2, contains two symmetry-independent molecules. The interplanar angles between the imidazole and phenyl ring planes are 16.35 (3) and 17.48 (6)°. Molecules are connected via N—H⋯N hydrogen bonds to form zigzag chains along the b axis. The title compound is the first example of a structurally characterized 4,5-diiodoimidazole with an organic substituent in the 2-position and without protection on the N—H group of imidazole.

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“…Halogenated imidazoles exhibit insecticidal [11], parasiticidal [12], acaricidal [13], and herbicidal [14] activity. Only few crystal structures of partially brominated imidazole [15] and quaternary imidazolium salts [16][17][18] have been reported. A cobalt complex of 2,4,5-tribromoimidazole has been published [19].…”

Section: Introductionmentioning

confidence: 99%