Tribromoisocyanuric Acid Research Articles

The use of tribromoisocyanuric acid to distinguish among primary, secondary and tertiary alcohols

Primary, secondary and tertiary alcohols can be easily distinguished due to their reactivity towards tribromoisocyanuric acid (TBCA). The test is performed by adding TBCA to the alcohol in a test tube heated in a boiling water bath. Orange color develops in the tube containing the primary alcohol, light yellow is observed in the tube containing the secondary alcohol while the tertiary alcohol results in a colorless mixture.

Casein kinase 2 inhibitor reduces androgen receptor function and cell proliferation in prostate cancer cells

Objective To investigate the role of casein kinase 2 (CK2) selective inhibitor tribromoisocyanuric acid (TBCA) in androgen receptor (AR) transactivation,cell proliferation and viability in prostate cancer cell lines,and explore a new chemotherapy for prostate cancer.Methods Prostate cancer cell lines were prepared.With TBCA treatment,Alamar-blue assay was performed to assess cell proliferation and viability in C4-2 cells and flow cytometry was performed for cell cycle analysis in C4-2 and 22Rvl cells; while immunofluorescence staining was performed to determine AR nuclear translocationin in PC-3/AR cells with R1881 pretreatment,and luciferase gene reporter assay was performed to determine AR transactivation in LNCaP cells; Reverse transcription-polymerase chain reaction (RT-PCR) was performed to evaluate the mRNA level of prostate specific antigen (PSA).Results With TBCA treatment,Alamar-blue reading decreased in a dose-dependent manner,and the 50％ inhibitory concentration ( IC50 ) was around 25 mol/L.Significant G2/M arrest was detected in C4-2 and 22Rvl cells.R1881-induced AR nuclear localization was reduced significantly ( P ＜ 0.01 ).R1881 -stimulated ARE-LUC reporter activity in LNCaP cells decreased with reduced level of PSA mRNA,which was an AR endogenous target( P ＜ 0.05 ).Conclusion The selective CK2 inhibitor TBCA can dramatically inhibite cell proliferation and cause a G2/M phase arrest in prostate cancer cells. Key words: Casein kinase 2; Prostate cancer; . Androgen receptor; Cell proliferation; Tribromoisocyanuric acid

Unexpected ring contraction and oxidation rearrangement reactions of securinine

The bromination and oxidation of securinine were studied. An interesting and surprising rearrangement was observed during the reaction of securinine with tribromo-isocyanuric acid or 1,3-dibromo-5,5-dimethylhydantoin in methanol, yielding a stereoselective ring contraction norsecurinine derivative. Meanwhile two oxidation rearrangement products were also reported. Some preliminary discussions on the reactivity of securinine were conducted from these rearrangements; it is believed to be induced by alkaline nitrogen atom of the molecule.

Tribromoisocyanuric Acid (TBCA)

This paper provides a description of tribromoisocyanuric acid (TBCA), a new reagent used as a source of electrophilic bromine (Br+) in organic synthesis, including in Green Chemistry procedures. Its applications embrace the bromination of alkenes, β-dicarbonyl compounds and deactivated arenes, as well as oxidations of urazoles, bisurazoles, and thiols.

Superelectrophilic bromination of deactivated aromatic rings with tribromoisocyanuric acid—an experimental and DFT study

The reaction of deactivated arenes with tribromoisocyanuric acid (TBCA) in 98% H 2SO 4 produced bromoarenes in good yields. The acidity of the medium controls the strength of the brominating agent and the amount of polybrominated products. DFT calculations at B3LYP/6-311++G ∗∗ level showed that the protonated TBCA (a superelectrophilic species) can easily transfer Br + to deactivated arenes, in order to decrease internal charge–charge repulsion.

Tribromoisocyanuric Acid and DABCO-Br as Efficient Catalysts for the Silylation of Hydroxyl Groups with Hexamethyldisilazane

Many primary, secondary, tertiary alcohols, and phenolic hydroxyl groups were effectively converted to their corresponding trimethylsilyl ethers using hexamethyldisilazane in the presence of catalytic amounts of tribromoisocyanuric acid and DABCO-bromine under mild conditions at room temperature with short reaction times in good to excellent yields. Excellent chemoselective silylation of hydroxyl groups in the presence of other functional groups were also observed.

Tribromoisocyanuric Acid (TBCA) and Oxone®‐MX Systems as Oxidizing Agents: Oxidative Coupling of Thiols to Their Corresponding Disulfides under Mild and Heterogeneous Conditions

AbstractTribromoisocyanuric acid (TBCA) and Oxone®‐MX systems were used as effective oxidizing agents for the oxidation of thiols to their corresponding disulfides under mild conditions at room temperature with good to excellent yields.

Tribromoisocyanuric Acid: A New Reagent for Regioselective Cobromination of Alkenes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Tribromoisocyanuric Acid: A New Reagent for Regioselective Cobromination of Alkenes

A simple one-step method for the preparation of tribromoisocyanuric acid in good yield (87%) has been developed. The reaction of tribromoisocyanuric acid with alkenes in presence of nucleophilic solvents (MeOH, i-PrOH, AcOH and a mixture of H 2 O-acetone, 1:5) led to the corresponding β-bromoethers, p-bromoacetates and bromohydrins, in high regioselectivity and good yields (73-98%).

A New Regioselective Bromination of Activated Aromatic Rings

An efficient and highly regioselective bromination of activated aromatic rings promoted by tribromoisocyanuric acid by in situ generation of Br+ has been developed. A range of aromatic compounds were reacted with tribromoisocyanuric acid and trichloroisocyanuric acid and sodium bromide.