6269-92-7

Usage

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 4135, 1991 DOI: 10.1016/S0040-4039(00)79884-4

InChI:InChI=1/C8H16Br2/c1-2-3-4-5-6-8(10)7-9/h8H,2-7H2,1H3

Upstream product

• 111-66-0 oct-1-ene 
• 67-56-1 methanol 
• 873-55-2 sodium benzenesulfonate 
• 75-05-8 acetonitrile 
• 71-36-3 butan-1-ol 
• 75-62-7 Bromotrichloromethane 
• 124-38-9 carbon dioxide 
• 2984-50-1 1,2-Epoxyoctane 
• 629-05-0 n-octyne 

Relevant academic research and scientific papers

Dibrominated addition and substitution of alkenes catalyzed by Mn2(CO)10

A practical method for the dibromination of alkenes without using molecular bromine is consistently appealing in organic synthesis. Herein, we report Mn-catalyzed dibrominated addition and substitution of alkenes only with N-bromosuccinimide, producing a variety of synthetically valuable dibrominated compounds in moderate to high yields. This journal is

Crystal structure, characterization, Hirshfeld surface analysis and DFT studies of two [propane 3-bromo-1-(triphenyl phosphonium)] cations containing bromide (I) and tribromide (II) anions: The anion (II) as a new brominating agent for unsaturated compounds

In this study, propane 3-bromo-1- (triphenyl phosphonium) bromide, I, and propane 3-bromo-1- (triphenyl phosphonium) tribromide, II, (II as a new brominating agent) were synthesized and characterized by 1H NMR, 13C NMR, 31P NMR, FT-IR, spectroscopy, Thermogravimetric Analysis, Differential thermal analysis, Differential scanning calorimetry and single crystal X-ray analysis. Density functional theory calculations (energy, structural optimization and frequencies, Natural Bond Orbital, absorption energy and binding energy) were performed by using B3LYP/6-311 G++ (d, p) level of theory. Hirshfeld surface analysis and fingerprint plots were utilized to investigate the role of bromide and tribromide anions on the crystal packing structures of title compounds. The results revealed that the change of accompanying anionic moiety can affect the directional interactions of C-H?Br hydrogen bonds between anionic and cationic units in which the H?Br with a proportion of 53.8% and 40.9% have the major contribution in the stabilization of crystal structures of I and II, respectively. Furthermore, the thermal stability of new brominating agent II with tribromide anion was compared with compound I with bromide anion. Nontoxicity, short reaction time, thermal stability, simple working up and high yield are some of the advantages of these salts.

Dibromination of alkenes with LiBr and H2O2 under mild conditions

Electron-rich and electron-poor alkenes, and alkenes bearing protecting groups can be efficiently and stereoselectively converted to trans-dibromides using LiBr/H2O2 and AcOH as a proton source in 1,4-dioxane. For most substrates addition of 0.1 mol% of PhTeTePh enhances the reaction rate and the yield of the products. Experimental data suggest that the brominating agent prepared in situ is molecular bromine and that LiBr assists the activation of H2O2 allowing bromination to occur using AcOH as a mild proton source in uncatalyzed experiments. Scale-up is feasible: 10.0 mmol of 1-octene was quantitatively converted to 1,2-dibromooctene in one hour of reaction at room temperature.

One-Pot Strategy for Thiazoline Synthesis from Alkenes and Thioamides

A convenient synthesis of a privileged pharmaceutical motif, thiazoline is accomplished. This reaction utilizes simple and readily available alkene and thioamide substrates in an intermolecular fashion via a simple one-pot procedure. A wide range of functional groups is tolerated, and the thiazoline product has been further utilized for the synthesis of the corresponding β-aminothiol and thiazole from routine hydrolysis and oxidation protocols.

Complexes of cis-dioxomolybdenum(VI) with a chiral tetradentate tripodal-like ligand system: Syntheses, structures and catalytic activities

Racemic complexes with the general formula cis-[MoO2(bzacLn)] (1–4) (H2bzacLn?=?2-((4/5-R-2-hydroxyphenylamino)(pyridin-2-yl)methyl)-1-phenylbutane-1,3-dione, where n?=?1–4 for R?=?H, 5-Me, 5-Cl and 4-Me, respectively and 2Hs represent the dissociable phenolic proton and the active tertiary CH proton) have been synthesized in 75–82% yields by reacting [MoO2(bzac)2] (Hbzac?=?benzoylacetone) with the potentially N2O-donor 5,5-membered fused chelate rings forming Schiff bases 4/5-R-2-(2-pyridylaldimine)phenols (HLn; n?=?1–4 for R?=?H, 4-Me, 4-Cl and 5-Me, respectively) in hot methanol. The chiral ligand system (bzacLn)2?in 1–4 is formed via metal assisted Mannich-type addition of benzoylacetonate methine to the azomethine fragment of HLn. All four complexes have been characterized by elemental (CHN) analysis, solution conductivity, magnetic susceptibility, spectroscopic (IR, UV–Vis and NMR) and electrochemical measurements. The molecular structures of 1–3 have been established by single crystal X-ray crystallography. In each complex, the chiral (bzacLn)2?acts as a tetradentate, N2O2-donor, tripodal-like ligand system and along with the two mutually cis oxo groups forms a distorted octahedral N2O4coordination environment around the molybdenum(VI) center. All four complexes are diamagnetic and non-electrolytic. The infrared spectra are generally consistent with the structural formulas of 1–4. The electronic spectra of 1–4 in dimethylformamide display two strong absorption bands in the range 245–300?nm. The cyclic voltammograms of 1–4 in dimethylformamide exhibit a metal centered one-electron reduction response within ?0.64 to ?0.74?V. All these complexes (1–4) and the analogous cis-[MoO2(acacL1–4)] (5–8) synthesized from [MoO2(acac)2] (Hacac?=?acetylacetone) and HL1–4have been evaluated for their bromoperoxidase activities.

Effective bromo and chloro peroxidation catalysed by tungsten(vi) amino triphenolate complexes

Amino triphenolate tungsten(vi) complexes have been prepared and they proved to be efficient catalysts in haloperoxidation reactions using hydrogen peroxide as a terminal oxidant and inorganic sources of halides. In particular, interesting results have been obtained in the challenging chloroperoxidation reactivity (catalyst loading down to 0.05% with TONs up to 900). A comparison among three different metal complexes bearing the same ligand (vanadium(v), molybdenum(vi) and tungsten(vi)) showed much better performances of the last complex both on bromo and chloro peroxidations.

Trihaloisocyanuric Acid/Triphenylphosphine: An Efficient System for Regioselective Conversion of Epoxides into Vicinal Halohydrins and Vicinal Dihalides under Mild Conditions

A new synthetic method has been developed for the regioselective conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides by reaction with the system trihaloisocyanuric acid/tri?phenylphosphine in acetonitrile under mild and neutral conditions. The reactions proceed smoothly in high yield at room temperature and at reflux, respectively, over a short time.

Cis-Dioxomolybdenum(VI) complexes with unsymmetric linear tetradentate ligands: Syntheses, structures and bromoperoxidase activities

Reactions of [MoO2(acetylacetonate)2], 2-((2-(2-hydroxyethylamino)ethylamino)methyl)-4-R-phenols (H2Ln, n = 1-5 for R = H, Me, OMe, Cl and Br, respectively) and KOH in 1:1:2 mole ratio in methanol afford a series of complexes having the general formula cis-[MoO2(Ln)] (1, 2, 3, 4, 5) in 81-86% yields. The complexes have been characterized using elemental analysis, spectroscopy (infrared, UV-visible, and 1H NMR, 13C NMR and 13C-DEPT NMR) and electrochemical measurements. The molecular structures of 1, 2, 3, 4 have been determined using single-crystal X-ray crystallography. In each of 1, 2, 3, 4, the ONNO-donor 6,5,5-membered fused chelate rings forming (Ln)2- and the two mutually cis oxo groups assemble a distorted octahedral N2O4 coordination sphere around the metal centre. In the crystal lattice, each of 1, 2, 3, 4 forms a one-dimensional infinite chain structure via intermolecular N-H...O hydrogen bonding interactions. In cyclic voltammograms, the diamagnetic complexes display an irreversible metal-centred reduction in the potential range -0.73 to -0.88 V (vs Ag/AgCl). The physicochemical data are consistent with a very similar gross molecular structure for all of 1, 2, 3, 4, 5. All the complexes exhibit decent bromoperoxidase activities and are also able to effectively catalyse benzoin and methyl(phenyl)sulfide oxidation reactions.

Bromination of olefins with HBr and DMSO

A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.

Synthesis and oxidation catalysis of a Ti-substituted phosphotungstate, and identification of the active oxygen species

In this paper, we report the synthesis of a Ti-substituted phosphotungstate, TBA6[(γ-PW10O36)2Ti4(μ-O)2(μ-OH)4] (I, TBA = tetra-n-butylammonium), and its application to H2O2-based oxidation. Firstly, an organic solvent-soluble dilacunary phosphotungstate precursor, TBA3[γ-PW10O34(H2O)2] (PW10), has been synthesized. By the reaction of PW10 and TiO(acac)2 (acac = acetylacetonate) in an organic medium (acetonitrile), I can be obtained. Compound I possesses a tetranuclear Ti core which can effectively activate H2O2 and shows high catalytic performance for several oxidation reactions, such as epoxidation of alkenes, oxygenation of sulfides, oxidative bromination of unsaturated compounds, and hydroxylation of anisole, giving the corresponding oxidation products with high efficiencies and selectivities. The catalytic performance of I is much superior to those of previously reported Ti-substituted polyoxometalates. In addition, I is highly durable during catalysis and can be reused several times while keeping its high catalytic performance. Furthermore, we have successfully isolated the truly catalytically active species for the present I-catalyzed oxidation, TBA6[(γ-PW10O36)2Ti4(μ-η2:η2-O2)4] (II), and its anion structure has been determined by X-ray crystallographic analysis. All of the four Ti2-μ-η2:η2-peroxo species in II are active for stoichiometric oxidation (without H2O2), and II is included in the catalytic cycle for I-catalyzed oxidation.