586-61-8

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C9H11Br/c1-7(2)8-3-5-9(10)6-4-8/h3-7H,1-2H3

Upstream product

• 98-82-8 Isopropylbenzene 
• 108-86-1 bromobenzene 
• 540-54-5 1-Chloropropane 
• 75-29-6 isopropyl chloride 
• 6888-79-5 4-bromo-α-methylstyrene 
• 106-94-5 propyl bromide 
• 67-63-0 isopropyl alcohol 
• 75-26-3 isopropyl bromide 
• 7637-07-2 boron trifluoride 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 99-90-1 para-bromoacetophenone 

Downstream Products

• 6962-76-1 dihydroxy-(4-isopropenyl-phenyl)-borane 
• 536-66-3 p-isopropylbenzoic acid 
• 3172-11-0 4-bromocumene hydroperoxide 
• 18970-30-4 4,4' diisopropylbiphenyl 
• 18620-03-6 4-isopropylphenylmagnesium bromide 
• 33786-51-5 (Z)-4-(p-Isopropylphenyl)-3-hepten 
• 33786-52-6 (E)-4(p-Isopropylphenyl)-3-hepten 
• 16483-41-3 2,3-Di-(4-brom-phenyl)-2,3-dimethyl-butan 
• 17797-12-5 1-(4-bromophenyl)-1-methylethylamine 
• 57803-89-1 3-(4-isopropylphenyl)-1H-indene 
• 93741-44-7 1-((E)-3,7-Dimethyl-octa-2,6-dienyl)-4-isopropyl-benzene 
• 93741-51-6 1-(1,5-Dimethyl-hex-4-enyl)-4-isopropyl-benzene 
• 90900-81-5 1-Isopropyl-4-undec-10-enyl-benzene 
• 128881-97-0 1-((E)-5,9-Dimethyl-deca-4,8-dienyl)-4-isopropyl-benzene 

Relevant academic research and scientific papers

Cobalt-Catalyzed Hydrogenations via Olefin Cobaltate and Hydride Intermediates

Redox noninnocent ligands are a promising tool to moderate electron transfer processes within base-metal catalysts. This report introduces bis(imino)acenaphthene (BIAN) cobaltate complexes as hydrogenation catalysts. Sterically hindered trisubstituted alkenes, imines, and quinolines underwent clean hydrogenation under mild conditions (2-10 bar, 20-80 °C) by use of the stable catalyst precursor [(DippBIAN)CoBr2] and the cocatalyst LiEt3BH. Mechanistic studies support a homogeneous catalysis pathway involving alkene and hydrido cobaltates as active catalyst species. Furthermore, considerable reaction acceleration by alkali cations and Lewis acids was observed. The dinuclear hydridocobaltate anion with bridging hydride ligands was isolated and fully characterized.

Amine-Borane Dehydrogenation and Transfer Hydrogenation Catalyzed by α-Diimine Cobaltates

Anionic α-diimine cobalt complexes, such as [K(thf)1.5{(DippBIAN)Co(η4-cod)}] (1; Dipp=2,6-diisopropylphenyl, cod=1,5-cyclooctadiene), catalyze the dehydrogenation of several amine-boranes. Based on the excellent catalytic properties, an especially effective transfer hydrogenation protocol for challenging olefins, imines, and N-heteroarenes was developed. NH3BH3 was used as a dihydrogen surrogate, which transferred up to two equivalents of H2 per NH3BH3. Detailed spectroscopic and mechanistic studies are presented, which document the rate determination by acidic protons in the amine-borane.

Olefin-Stabilized Cobalt Nanoparticles for C=C, C=O, and C=N Hydrogenations

The development of cobalt catalysts that combine easy accessibility and high selectivity constitutes a promising approach to the replacement of noble-metal catalysts in hydrogenation reactions. This report introduces a user-friendly protocol that avoids complex ligands, hazardous reductants, special reaction conditions, and the formation of highly unstable pre-catalysts. Reduction of CoBr2 with LiEt3BH in the presence of alkenes led to the formation of hydrogenation catalysts that effected clean conversions of alkenes, carbonyls, imines, and heteroarenes at mild conditions (3 mol % cat., 2–10 bar H2, 20–80 °C). Poisoning studies and nanoparticle characterization by TEM, EDX, and DLS supported the notion of a heterotopic catalysis mechanism.

Alkene Hydrogenations by Soluble Iron Nanocluster Catalysts

The replacement of noble metal technologies and the realization of new reactivities with earth-abundant metals is at the heart of sustainable synthesis. Alkene hydrogenations have so far been most effectively performed by noble metal catalysts. This study reports an iron-catalyzed hydrogenation protocol for tri- and tetra-substituted alkenes of unprecedented activity and scope under mild conditions (1–4 bar H2, 20 °C). Instructive snapshots at the interface of homogeneous and heterogeneous iron catalysis were recorded by the isolation of novel Fe nanocluster architectures that act as catalyst reservoirs and soluble seeds of particle growth.

Iron-catalyzed olefin hydrogenation at 1 bar H2 with a FeCl3-LiAlH4 catalyst

The scope and mechanism of a practical protocol for the iron-catalyzed hydrogenation of alkenes and alkynes at 1 bar H2 pressure were studied. The catalyst is formed from cheap chemicals (5 mol% FeCl3-LiAlH4, THF). A homogeneous mechanism operates at early stages of the reaction while active nanoparticles form upon ageing of the catalyst solution. This journal is

On the ionizing properties of supercritical carbon dioxide: Uncatalyzed electrophilic bromination of aromatics

Supercritical carbon dioxide (scCO2), a solvent with a zero dipole moment, low dielectric constant, and no hydrogen bonding behavior, is a suitable medium to perform the uncatalyzed electrophilic bromination of weakly activated aromatics with no interference of radical pathways. The ability of scCO2 to promote these reactions matches those of strongly ionizing solvents such as aqueous acetic and trifluoroacetic acids. Conversely, carbon tetrachloride, with similar polarity parameters to scCO2, leads exclusively to side chain functionalization. The strong quadrupole moment, and the acidic, but non basic, Lewis character of carbon dioxide, are proposed as key factors for the singular performance of scCO2 in reactions involving highly polar and ionic intermediates.

Metal and H2O2 free aerobic oxidative aromatic halogenation with [RNH3+] [NO3-]/HX and [BMIM(SO3H)][NO3)x(X)y] (X = Br, Cl) as multifunctional ionic liquids

Novel multifunctional ionic liquids (ILs) are generated by addition of HBr or HCl to alkylammonium nitrates ([RNH3+] [NO 3-]) and to 3-methyl-1-(butyl-4-sulfonyl)imidazolium nitrate ([BMIM(SO3H)][NO3]). The resulting [RNH 3+] [NO3-]/HX and mono (3-methyl-1-(butyl-4-sulfonyl)imidazolium) monohalogenide mononitrate ([BMIM(SO3H)][NO3)x(X)y] (X = Br, Cl)) systems act as solvent and promoter for aerobic oxidative halogenation of arenes under mild conditions in high yields that can be repeated over several cycles.

Bromination of alkylbenzenes in 1-butyl-3-methylimidazolium bromide and its dibromide complex

Alkylbenzenes were subjected to bromination with molecular bromine using 1-butyl-3-methylimidazolium bromide as solvent. A complex of 1-butyl-3-methylimidazolium bromide with bromine was synthesized. It ensured bromination of alkylbenzenes with no bromine and solvent. The results of bromination in binary solvents and ionic liquids, 1-butyl-3-methylimidazolium bromide and tribromide were compared. The bromination of ethylbenzene with 1-butyl-3-methylimidazolium tribromide was accompanied by formation of a considerable amount of α-bromoethylbenzene, which is not typical of electrophilic aromatic substitution process.

M -Azipropofol (AziP m) a photoactive analogue of the intravenous general anesthetic propofol

Propofol is the most commonly used sedative-hypnotic drug for noxious procedures, yet the molecular targets underlying either its beneficial or toxic effects remain uncertain. In order to determine targets and thereby mechanisms of propofol, we have synthesized a photoactivateable analogue by substituting an alkyldiazirinyl moiety for one of the isopropyl arms but in the meta position. m-Azipropofol retains the physical, biochemical, GABAA receptor modulatory, and in vivo activity of propofol and photoadducts to amino acid residues in known propofol binding sites in natural proteins. Using either mass spectrometry or radiolabeling, this reagent may be used to reveal sites and targets that underlie the mechanism of both the desirable and undesirable actions of this important clinical compound.

Induced bromination of aromatic hydrocarbons with alkali metal bromides in the presence of oxidants

The features of induced bromination of aromatic hydrocarbons in the NaBr(KBr)-HX-H2O2(NaOCl) system were studied. Pleiades Publishing, Inc., 2006.