7116-96-3

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Intermediates of Liquid Crystals

General Description

The orientational relaxation and spectral diffusion of 4-pentyl-4′-thiocyanobiphenyl (5SCB) in 4-pentylbiphenyl (5B) at various temperatures was studied.

InChI:InChI=1/C17H20/c1-2-3-5-8-15-11-13-17(14-12-15)16-9-6-4-7-10-16/h4,6-7,9-14H,2-3,5,8H2,1H3

Upstream product

• 42916-73-4 1-[1,1'-biphenyl]-4-yl-1-pentanone 
• 121219-12-3 (4-pentylphenyl)boronic acid 
• 106-40-1 4-bromo-aniline 
• 540-37-4 p-aminoiodobenzene 
• 92-52-4 biphenyl 
• 51554-95-1 4-pentylbromobenzene 
• 98-80-6 phenylboronic acid 
• 613-37-6 4-methoxylbiphenyl 
• 3814-99-1 pentylmagnesium iodide 
• 78322-97-1 phenyl [1,1′-biphenyl]-4-carboxylate 
• 308796-10-3 (1-pentyl)zinc(II) bromide 
• 188114-77-4 [1,1'-biphenyl]-4-yl pivalate 
• 324-74-3 4-fluoro-biphenyl 
• 693-25-4 n-pentylmagnesium bromide 

Downstream Products

• 63619-59-0 4-(4-pentylphenyl)bromobenzene 
• 69971-79-5 4-iodoo-4'-n-pentylbiphenyl 
• 42916-73-4 1-[1,1'-biphenyl]-4-yl-1-pentanone 
• 1325242-76-9 4-(α-benzoyloxypentyl)biphenyl 
• 1443253-85-7 4S-[2-fluoro-4-(2-methyl-1-butyl)phenyl]ethynyl-4'-pentylbiphenyl 
• 1443253-86-8 4S-[2,6-difluoro-4-(2-methyl-1-butyl)phenyl]ethynyl-4'-pentylbiphenyl 
• 56741-21-0 4'-pentyl-1,1'-biphenyl-4-carbaldehyde 
• 40817-08-1 4-cyano-4'-pentyl-1,1'-biphenyl 

Relevant academic research and scientific papers

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

Suzuki-Miyaura Cross-Coupling of Sulfoxides

The utilization of diphenyl sulfoxides as versatile electrophilic coupling partners for the Suzuki-Miyaura reaction via C-S bond cleavage was successfully developed under palladium-N-heterocyclic carbene catalysis. The reactions showed good functional group compatibility, proceeded well under mild conditions, and provided biaryls in yields of up to 96%. A wide range of useful functional groups, such as fluoro, chloro, ether, hydroxyl, amide, cyano, keto, trimethylsilyl (TMS), and ester were tolerated under the reaction conditions; however, the use of phenylboronic anhydride and arylboronic acid pinacol esters generally would lead low yields. Good regioselectivity for the electron-poor phenyl group was achieved when unsymmetrical diphenyl sulfoxides were used. The protocol is applicable at the gram scale even with half the amount of catalyst. Density functional theory calculations were performed to investigate the reaction mechanism, indicating that the reaction occurred through oxidative addition, transmetalation, and reductive elimination to provide the final coupling product.

C-F activation for C(sp2)-C(sp3) cross-coupling by a secondary phosphine oxide (SPO)-nickel complex

A secondary phosphine oxide (SPO)-nickel catalyst allowed the activation of otherwise inert C-F bonds of unactivated arenes in terms of challenging couplings with primary and secondary alkyl Grignard reagents. The C-F activation is characterized by mild reaction conditions and high levels of branched selectivity. Electron-rich and electron-deficient arenes were suitable electrophiles for this transformation. In addition, this strategy also proved suitable to heterocycles and for the activation of C-O bonds under slightly modified conditions.

Nickel-Catalyzed Csp2-Csp3 Bond Formation via C-F Bond Activation

A nickel-catalyzed cross coupling of aryl fluorides via C-F bond activation has been developed. The alkylation method allows selective replacement of aryl fluorides by alkyl groups and enables the synthesis of diverse and otherwise difficult to access scaffolds in good yields.

Alkylimidazole-Based Phosphines as Efficient Ligands for Palladium-Catalyzed Suzuki Reactions

Two series of alkylimidazole-based phosphines were conveniently synthesized in one step from the corresponding alkylimidazole by selective deprotonation and quenching with chlorodiphenylphosphine. The novel ligands are easily tunable and exhibit good-to-excellent performance in the palladium-catalyzed Suzuki coupling reaction.

Nickel-Catalyzed C-O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains

Two efficient protocols for the nickel-catalyzed aryl-alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C-O and aryl C-O bonds and allow the aryl-alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C-O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.

New low polar tolane cholesterics designed for infrared applications

We have designed, synthesized and evaluated the physical properties of new fluorinated phenyltolane based chiral liquid crystal materials with 2-methylbutyl terminal chain. The 2- or 2,6-fluorosubstitution in combination with the phenyltolane core brings surprising improvement of mesomorphic properties. The investigated compounds are characterized by a broad temperature range of the cholesteric (chiral nematic N?) phase, very low melting temperatures and easy thermal control of selective reflection in the near infrared region. The moderate helical twisting power β, high optical anisotropy and source of a blue phase make these compounds attractive for cholesteric mixture formulations.

Nickel-catalyzed alkylative cross-coupling of anisoles with grignard reagents via C-O bond activation

We report nickel-catalyzed cross-coupling of methoxyarenes with alkylmagnesium halides, in which a methoxy group is eliminated. A wide range of alkyl groups, including those bearing β-hydrogens, can be introduced directly at the ipso position of anisole derivatives. We demonstrate that the robustness of a methoxy group allows this alkylation protocol to be used to synthesize elaborate molecules by combining it with traditional cross-coupling reactions or oxidative transformation. The success of this method is dependent on the use of alkylmagnesium iodides, but not chlorides or bromides, which highlights the importance of the halide used in developing catalytic reactions using Grignard reagents.

Catalytic activity of 1-methylimidazole-based phosphine ligands in the palladium-catalyzed Suzuki coupling reaction

The catalytic activities of three N-methylimidazole-based phosphine ligands in the Suzuki coupling reaction were tested using PdCl2 as the catalyst. The results showed all three phosphine ligands exhibited excellent activity towards the Suzuki reaction, and the catalytic activity decreased with increasing number of imidazole groups.

The synthesis of chiral fluorinated 4-alkyl-4′-[(4-alkylphenyl) ethynyl]biphenyls

We have designed, synthesized, and evaluated the physical properties of new fluorinated phenyltolane based chiral liquid crystal materials with 2-methylbutyl chains. This type of fluoro-substitution in chemical combination with a phenyltolane core brings a surprising improvement to the mesomorphic properties. The investigated compounds exhibit broad temperature ranges for the N* phase and very low melting points. All homologues exhibited Blue Phase. We have applied a Cu-catalyzed cross-coupling reaction between aryl Grignard reagents and alkyl bromides for the synthesis of the products.