29536-28-5

Usage

Uses

Used in Lubricant Industry:
Benzene, 1,3,5-trihexylis used as a component in the preparation of lubricating oil and hydraulic fluid. Its hydrophobic nature and low polarity make it suitable for reducing friction and wear in mechanical systems.
Used in Pharmaceutical Industry:
Benzene, 1,3,5-trihexylis used as an inhibitor of the interaction between a steroid receptor coactivator and estrogen receptor α. This interaction plays a crucial role in the regulation of gene expression and cellular processes. By inhibiting this interaction, Benzene, 1,3,5-trihexylcan potentially be used in the development of drugs targeting hormone-related diseases and conditions.

Upstream product

• 108-70-3 1,3,5-trichlorobenzene 
• 3761-92-0 n-hexylmagnesium bromide 
• 61285-50-5 N-(1-methylheptylidene)benzeneamine 
• 62-53-3 aniline 
• 111-13-7 hexyl-methyl-ketone 
• 629-05-0 n-octyne 
• 6975-99-1 6-dodecyne 
• 111-25-1 1-bromo-hexane 
• 15226-74-1 dicobalt octacarbonyl 
• 201230-82-2 carbon monoxide 
• 4068-02-4 2,2-dimethyl-3-morpholino-3-oxopropanal 
• 100-47-0 benzonitrile 
• 79887-11-9 4-hexylphenylacetylene 
• 3223-40-3 3-oxo-octanal 

Downstream Products

• 155802-08-7 1,3,5-tri-N-hexyl-2,4,6-triiodobenzene 

Relevant academic research and scientific papers

Selective cyclotrimerization of acetylenes via tantalum-alkyne complexes

Tantalum-alkyne complexes from internal acetylenes and low-valent tantalum (TaCl5 and Zn) in DME and benzene react with terminal diynes in presence of THF and pyridine to give tetrasubstituted benzene derivatives in good to excellent yields.

H-BPin/KOtBu Promoted Activation of Cobalt Salt to a Heterotopic Catalyst for Highly Selective Cyclotrimerization of Alkynes

A mixture of HBPin with KOtBu was found to activate cobalt salt to form a heterotopic cobalt species that is highly active for catalytic intermolecular trimerization of alkynes. This protocol affords 1,2,4-regioisomers in good yields with high regioselectivities under mild conditions. These salient features, together with the operational simplicity and high efficiency, as well as obviating the use of any costly and/or air sensitive ligands, renders the protocol promising for practical applications.

Hydrogen-Bonding Controlled Nickel-Catalyzed Regioselective Cyclotrimerization of Terminal Alkynes

Herein we report a hydrogen-bonding controlled nickel-catalyzed regioselective cyclotrimerization of terminal alkynes in moderate to excellent yields with high regioselectivities toward 1,3,5-trisubstituted benzenes. This method features a cheap catalyst, mild reaction conditions, and excellent functional group compatibility. The Ni-B(OH)2 complex in situ generated from NiCl2·DME and tetrahydroxydiboron might act as an active catalyst. After three consecutive cis-additions of terminal alkynes, internal migratory insertion cyclization, and β-boron elimination induced aromatization, 1,3,5-trisubstituted benzenes were selectively established.

Synthesis method of 1,3,5-trisubstituted aryl compound

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of a 1,3,5-trisubstituted aryl compound. The method is carried out according to a process route as described in a formula (III). In the formula (III), R, R and R are any substituent group, X is C-R, and R is H or any other substituent group. The invention provides the novel method for synthesizing the 1,3,5-trisubstituted aryl compound. The large-scale production and application of the 1,3,5-trisubstituted aryl compound are greatly promoted.

Combined Photoredox and Iron Catalysis for the Cyclotrimerization of Alkynes

Successful combinations of visible-light photocatalysis with metal catalysis have recently enabled the development of hitherto unknown chemical reactions. Dual mechanisms from merging metal-free photocatalysts and earth-abundant metal catalysts are still in their infancy. We report a photo-organo-iron-catalyzed cyclotrimerization of alkynes by photoredox activation of a ligand-free Fe catalyst. The reaction operates under very mild conditions (visible light, 20 °C, 1 h) with 1–2 mol percent loading of the three catalysts (dye, amine, FeCl2).

Three-Coordinate Iron(0) Complexes with N-Heterocyclic Carbene and Vinyltrimethylsilane Ligation: Synthesis, Characterization, and Ligand Substitution Reactions

Low-coordinate iron(0) species are implicated as intermediates in a range of iron-catalyzed organic transformations. Isolable iron(0) complexes with coordination numbers of less than four, however, are rarely known. In continuing with our interests in three-coordinate iron(0) complexes with N-heterocyclic carbene (NHC) and alkene ligation, we report herein the synthesis and ligand substitution reactivity of three-coordinate iron(0) complexes featuring monodentate alkene ligands, [(NHC)Fe(η2-vtms)2] (vtms = vinyltrimethylsilane, NHC = 1,3-bis(2′,6′-diisopropylphenyl)-imidazol-2-ylidene (IPr), 1; 1,3-bis(2′,6′-diisopropylphenyl)-4,5-tetramethylene-imidazol-2-ylidene (cyIPr), 2; 1,3-bis(2′,6′-diisopropylphenyl)-4,5,6,7-tetrahydro-1,3-diazepin-2-ylidene (7-IPr), 3). Complexes 1-3 were synthesized from the one-pot reactions of ferrous dihalides with the N-(2,6-diisopropylphenyl)-substituted NHC ligands, vtms, and KC8. Reactivity study of 1 revealed its facile ligand substitution reactions with terminal aryl alkynes, ketones, isocyanides, and CO, by which iron(0) complexes [(IPr)Fe(η2-HCCAr)] (Ar = Ph, 5; p-CH3C6H4, 6; 3,5-(CF3)2C6H3, 7), [(IPr)Fe(η2-OCPh2)2] (8), [(IPr)Fe(CNR)4] (R = 2,6-Me2C6H3, 9; But, 10), and (IPr)Fe(CO)4 (11) were prepared in good yields. These iron(0) complexes have been characterized by 1H NMR, solution magnetic susceptibility measurement, single-crystal X-ray diffraction study, 57Fe M?ssbauer spectroscopy, and elemental analysis. Characterization data and computational studies suggest S = 1 ground-spin states for three-coordinate iron(0) complexes 1-3 and 5-8 and S = 0 ground states for 9-11. Theoretical studies on the three-coordinate complexes 1, 6, and 8 indicated pronounced metal-to-ligand backdonation from occupied Fe 3d orbitals to the π* orbitals of the C= C, C=C, and C= O moieties of the πligands. In addition, 1 proved an effective precatalyst for the cyclotrimerization reaction of alkynes.

METHOD FOR PRODUCING BENZENE COMPOUND AND CATALYST FOR PRODUCING BENZENE COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing a benzene compound capable of performing production of various benzene compounds with low environmental load without generating waste as in the case of using benzene as a starting raw material and to provide a catalyst used for the production method. SOLUTION: There are provided: a method for producing a benzene compound from alkynes in the presence of a catalyst, wherein the catalyst is a PdAu supported catalyst obtained by supporting Pd and Au in a molar ratio of 1:1 to 1:10 on a carrier; and a catalyst used for the production method. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

One-pot synthesis of 2,3,5-substituted 1H-pyrroles via the reaction of terminal acetylenes with nitriles and EtAlCl2 catalyzed by Сp2TiCl2

A new one pot method for the synthesis of 2,3,5-substituted 1H-pyrroles in moderate to good yields (58–77%) based on multicomponent reaction of terminal acetylenes with nitriles and EtAlCl2 in the presence of Сp2TiCl2 cata

Concerted Catalysis by Adjacent Palladium and Gold in Alloy Nanoparticles for the Versatile and Practical [2+2+2] Cycloaddition of Alkynes

A Pd-Au alloy efficiently catalyzed the [2+2+2] cycloaddition of substituted alkynes. Whereas monometallic Pd and Au catalysts were totally ineffective, Pd-Au alloy nanoparticle catalysts with a low Pd/Au molar ratio showed high activity to give the corresponding polysubstituted arenes in high yields. A variety of substituted alkynes participated in various modes of cycloaddition under Pd-Au alloy catalysis. The Pd-Au alloy catalysts exhibited high air tolerance and reusability.

Rh(DPEPhos)-Catalyzed Alkyne Hydroacylation Using β-Carbonyl-Substituted Aldehydes: Mechanistic Insight Leads to Low Catalyst Loadings that Enables Selective Catalysis on Gram-Scale

The detailed mechanism of the hydroacylation of β-amido-aldehyde, 2,2-dimethyl-3-morpholino-3-oxopropanal, with 1-octyne using [Rh(cis-κ2-P,P-DPEPhos)(acetone)2][BArF4]-based catalysts, is described [ArF = (CF3)2C6H3]. A rich mechanistic landscape of competing and interconnected hydroacylation and cyclotrimerization processes is revealed. An acyl-hydride complex, arising from oxidative addition of aldehyde, is the persistent resting state during hydroacylation, and quaternary substitution at the β-amido-aldehyde strongly disfavors decarbonylation. Initial rate, KIE, and labeling studies suggest that the migratory insertion is turnover-limiting as well as selectivity determining for linear/branched products. When the concentration of free aldehyde approaches zero at the later stages of catalysis alkyne cyclotrimerization becomes competitive, to form trisubstituted hexylarenes. At this point, the remaining acyl-hydride turns over in hydroacylation and the free alkyne is now effectively in excess, and the resting state moves to a metallacyclopentadiene and eventually to a dormant α-pyran-bound catalyst complex. Cyclotrimerization thus only becomes competitive when there is no aldehyde present in solution, and as aldehyde binds so strongly to form acyl-hydride when this happens will directly correlate to catalyst loading: with low loadings allowing for free aldehyde to be present for longer, and thus higher selectivites to be obtained. Reducing the catalyst loading from 20 mol % to 0.5 mol % thus leads to a selectivity increase from 96% to ～100%. An optimized hydroacylation reaction is described that delivers gram scale of product, at essentially quantitative levels, using no excess of either reagent, at very low catalyst loadings, using minimal solvent, with virtually no workup.