Copper(II) Bromide: A Simple and Selective Monobromination Reagent for Electron‐Rich Aromatic Compounds.

Bhatt, Suchitra; Nayak, Sandip K.

doi:10.1002/chin.200741040

Cited by 2 publications

(4 citation statements)

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“…Following the homopolymer and network syntheses, the resulting polymers were functionalized by bromination with a bromine solution in carbon tetrachloride or a milder bromination agent, copper(II) bromide in DMF. Bromination by CuBr 2 is known, but has not been reported for polymers such as PMAi and analogues. The obtained brominated polymers were capable of degrading hydrazines, pesticides such as malathion (2-(dimethoxyphosphinothioylthio)butanedioic acid diethyl ester), which is a good VX- mimicking agent, and 2-chloroethyl ethyl sulfide (CEES), often used as a simulant for the vesicant HD CWA.…”

Section: Introductionmentioning

confidence: 99%

Degradation of Chemical Threats by Brominated Polymer Networks

Bromberg

Pomerantz

Schreuder-Gibson

et al. 2014

Ind. Eng. Chem. Res.

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Poly(N-bromomaleimide) (PMAi-Br), poly(N-vinylpyrrolidone)-bromine adducts (PVP–Br), and poly(ethylene-alt-N-bromomaleimide) (PEMAi-Br) and their cross-linked networks are introduced as reactive, self-decontaminating components of protective barriers. Synthetic routes toward polymaleimides include free-radical copolymerization of maleimide with divinyl cross-linkers as well as amidation of poly(ethylene-alt-maleic anhydride) with urea. The polymers are brominated by bromine in carbon tetrachloride or by copper(II) bromide in dimethylformamide, with the active bromine contents up to and above 4 mequiv/g, or >30 wt %. The brominated polymer networks exhibit considerable swelling in water and possess reversible redox peak potentials in cyclic voltammetry experiments due to the redox reactions of the bromine present in the polymer structures. In acidic aqueous media, PVP–Br, PMAi-co-DVB-Br, and PEMAi-Br materials are able to degrade 100% of hydrazine, monomethylhydrazine, and 1,1-dimethylhydrazine down to concentrations below detectable levels of 0.15–0.25 mM. The hydrazine is converted to nitrogen gas. The insecticide malathion, tested as a simulant of a combat warfare agent VX, is efficiently and selectively oxidized to malaoxon in the presence of the brominated networks, whereas 2-(chloroethyl)ethyl sulfide (CEES), a simulant of the sulfur mustard agent, is rapidly oxidized, in both vapor and liquid states, into its less-toxic sulfone derivative, 1-chloro-2-(ethylsulfinyl)ethane (CEESO), with the only side product being 1,2-bis(ethylthio)ethane. The oxidation of CEES is proven to be selective, in that no toxic overoxidized CEES analogue, 1-chloro-2-(ethylsulfonyl)ethane, is formed. The developed brominated polymer networks are versatile materials with potential applications in coatings, filters, fabrics, and sorbents.

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Section: Introductionmentioning

confidence: 99%

Degradation of Chemical Threats by Brominated Polymer Networks

Bromberg

Pomerantz

Schreuder-Gibson

et al. 2014

Ind. Eng. Chem. Res.

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show abstract

“…This condensation is best conducted (see Table 1) in the presence of Pd(Ph 3 P) 4 , Ph 3 P, and triethylamine (TEA) as a base in dimethylformamide (DMF) at 95-100 °C with 80% E/Z 2:1) conversion. This crude product is purified by column chromatography to get the pure (E)-2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-phenyl)-acrylamide (HPLC purity >99%, mp 144.6-146.1 °C) [10] with moderate yield (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

“…Initially condensation was tried with bromo derivative 2 (R = H, NO 2 ) [10,11] and 2-cyano-N,N-diethylacrylamide 3, which is prepared according to literature procedure [12] with various Pd sources and bases at 80-150 °C but the reaction did not proceed (Scheme 1) to give Heck product 4.…”

Section: Resultsmentioning

confidence: 99%