192865-77-3

Usage

Uses

Used in Organic Synthesis:
[1,1'-Biphenyl]-4-carboxylic acid, 4'-(dimethylamino)-, ethyl ester is used as a building block in the synthesis of various organic compounds. Its unique structure and functional groups make it a valuable component in creating a wide range of molecules for different applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, [1,1'-Biphenyl]-4-carboxylic acid, 4'-(dimethylamino)-, ethyl ester is used as a potential candidate for drug discovery and development. Its dimethylamino group and ester functional group contribute to its potential pharmacological properties, making it a promising compound for further research and development into new medications.
Used in Chemical Research:
[1,1'-Biphenyl]-4-carboxylic acid, 4'-(dimethylamino)-, ethyl ester is also utilized in chemical research to study its properties and interactions with other molecules. Understanding its reactivity and behavior can lead to the development of new synthetic methods and applications in various scientific fields.

Upstream product

• 5798-75-4 Ethyl 4-bromobenzoate 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 131379-16-3 4-(ethoxycarbonyl)phenylzinc iodide 
• 10287-53-3 ethyl p-dimethyaminolbenzoate 
• 1394949-85-9 C₁₂H₁₈NO₂⁽¹⁺⁾*Br^(1-) 
• 93296-10-7 (4-(dimethylamino)phenyl)zinc(II) chloride 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 28611-39-4 4-(dimethylamino)benzene-boronic acid 
• 121-69-7 N,N-dimethyl-aniline 
• 28276-32-6 ethyl p-mercaptobenzoate 

Relevant academic research and scientific papers

Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents

Cross-coupling of (hetero)arylthiols with arylzinc reagents via C-S cleavage was performed under transition-metal-free conditions. The reaction displays a wide scope of substrates and high functional-group tolerance. Electron-rich and -deficient (hetero)arylthiols and arylzinc reagents can be employed in this transformation. Mg2+ and Li+ ions were demonstrated to facilitate the reaction.

Boron-Catalyzed Aromatic C-H Bond Silylation with Hydrosilanes

Metal-free catalytic C-H silylation of a series of aromatic compounds such as N,N-disubstituted anilines with various hydrosilanes has been achieved for the first time using commercially available B(C6F5)3 as a catalyst. This protocol features simple and neutral reaction conditions, high regioselectivity, wide substrate scope (up to 40 examples), Si-Cl bond compatibility, and no requirement for a hydrogen acceptor.

New hydrogen halide salt

PROBLEM TO BE SOLVED: To provide novel substances excellent in water solubility and available as luminescent substrates in firefly bioluminescent systems.SOLUTION: There are provided hydrogen halide salts of compounds represented by the specified general formula (I) or the specified general formula (II).

Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore

New firefly luciferin analogs of the 4,4′-substituted biphenyl-type were synthesized. One analog with a 4′-dimethylamino group possessed bioluminescence activity, emitting near-infrared biological window light at 675 nm suitable for deep-site bioimaging of living animals. The chemiluminescence light-emission maximum of the corresponding methyl ester of the bioluminescence active analog was 500 nm, implying that biphenyl and thiazolinone rings in the light emitter might be placed in a coplanar conformation at the polar luciferase active site.

Nickel complexes supported by quinoline-based ligands: Synthesis, characterization and catalysis in the cross-coupling of arylzinc reagents and aryl chlorides or aryltrimethylammonium salts

Lithium and nickel complexes bearing quinoline-based ligands have been synthesized and characterized. Reaction of 8-azidoquinoline with Ph 2PNHR (R = p-MeC6H4, But) affords N-(8-quinolyl)iminophosphoranes RNHP(Ph2)N(8-C9H 6N) (1a, R = p-MeC6H4; 1b, R = But. C9H6N = quinolyl)). Reaction of 1a with (DME)NiCl 2 generates a nickel complex [NiCl2{N(8-C 9H6N)P(Ph2)NH(p-MeC6H4)}] (2a). Treatment of 1b with (DME)NiCl2 and following with NaH produces [NiCl{(1,2-C6H4)P(Ph)(NHBut)N(8-C 9H6N)}] (4). Complex 4 was also obtained by reaction of (DME)NiCl2 with [Li{(1,2-C6H4)P(Ph)(NHBu t)N(8-C9H6N)}] (5) prepared through lithiation of 1b. Reaction of 2-PyCH2P(Ph2)N(8-C9H 6N) (6, Py = pyridyl) and PhNC(Ph)CH2P(Ph 2)N(8-C9H6N) (8), respectively, with (DME)NiCl2 yields two five-coordinate N,N,N-chelate nickel complexes, [NiCl2{2-PyCH2P(Ph2)N(8-C9H 6N)}] (7) and [NiCl2{PhNC(Ph)CH2P(Ph 2)N(8-C9H6N)}] (9). Similar reaction between Ph2PCH2P(Ph2)N(8-C9H6N) (10) and (DME)NiCl2 results in five-coordinate N,N,P-chelate nickel complex [NiCl2{Ph2PCH2P(Ph2)N(8- C9H6N)}] (11). Treatment of [(8-C9H 6N)NP(Ph2)]2CH2 (12) [prepared from (Ph2P)2CH2 and 2 equiv. of 8-azidoquinoline] with LiBun and (DME)NiCl2 successively affords [NiCl{(8-C9H6N)NP(Ph2)}2CH] (13). The new compounds were characterized by 1H, 13C and 31P NMR spectroscopy (for the diamagnetic compounds), IR spectroscopy (for the nickel complexes) and elemental analysis. Complexes 2a, 4, 7, 9, 11 and 13 were also characterized by single-crystal X-ray diffraction techniques. The nickel complexes were evaluated for the catalysis in the cross-coupling reactions of arylzinc reagents with aryl chlorides and aryltrimethylammonium salts. Complex 7 exhibits the highest activity among the complexes in catalyzing the reactions of arylzinc reagents with either aryl chlorides or aryltrimethylammonium bromides.

[Pd(Cl)2(P(NC5H10)(C6H 11)2)2] - A highly effective and extremely versatile palladium-based negishi catalyst that efficiently and reliably operates at low catalyst loadings

[Pd(Cl)2(P(NC5H10)-(C6H 11)2]2] (1) has been prepared in quantitative yield by reacting commercially available [Pd(cod)(Cl)2] (cod = cyclooctadiene) with readily prepared 1-(dicyclohexylphosphanyl)piperidine in toluene under N2 within a few minutes at room temperature. Complex 1 has proved to be an excellent Negishi catalyst, capable of quantitatively coupling a wide variety of electronically activated, non-activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100°C in the presence of just 0.01 mol% of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetais, lactones, amides, anilines, alkenes, carboxylic acids, acetic acids, and pyridines and pyrimidines, have been successfully used as coupling partners. Furthermore, electronic and steric variations are tolerated in both reaction partners. Experimental observations strongly indicate that a molecular mechanism is operative.

Palladium-catalyzed selective synthesis of unsymmetrical biaryls from aryl halides or triflates and organomanganese reagents

Various functionalized unsymmetrical biaryls can be prepared in good to excellent isolated yields by palladium-catalyzed coupling reaction of aryl manganese chloride with aryl iodides, bromides or triflates. The reaction takes place rapidly and cleanly under mild conditions by using only 1% of palladium complexes.