2143-87-5

Basic information

• Product Name: 4-DIMETHYLAMINO-4'-NITROBIPHENYL
• Synonyms: 4-DIMETHYLAMINO-4'-NITROBIPHENYL;Dimethylaminonitrobiphenyl
• CAS NO: 2143-87-5
• Molecular Formula: C14H14N2O2
• Molecular Weight: 242.27
• Product Categories: Biphenyls (for High-Performance Polymer Research);Functional Materials;Organic Nonlinear Optical Materials;Reagent for High-Performance Polymer Research
• Mol File: 2143-87-5.mol

Chemical Properties

• Melting Point: 243.0 to 249.0 °C
• Boiling Point: 398.2oC at 760 mmHg
• Flash Point: 194.6oC
• Appearance: /
• Density: 1.184g/cm3
• Vapor Pressure: 1.5E-06mmHg at 25°C
• Refractive Index: 1.618
• PKA: 3.97±0.12(Predicted)
• CAS DataBase Reference: 4-DIMETHYLAMINO-4'-NITROBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-DIMETHYLAMINO-4'-NITROBIPHENYL(2143-87-5)
• EPA Substance Registry System: 4-DIMETHYLAMINO-4'-NITROBIPHENYL(2143-87-5)

Safety Data

• Hazardous Substances Data: 2143-87-5(Hazardous Substances Data)

Usage

Uses

Used in Dye Production:
4-Dimethylamino-4'-nitrobiphenyl is used as a dye precursor for the coloring of various materials, including plastics, textiles, and paper. Its chemical properties allow for the creation of vibrant and long-lasting colors in these substrates.
Used in Synthesis of UV-Curable Coatings:
In the coatings industry, 4-Dimethylamino-4'-nitrobiphenyl is utilized as a component in the synthesis of UV-curable coatings. These coatings are valued for their rapid curing properties under ultraviolet light, which enhances production efficiency and results in durable, high-quality finishes.
Used in Photoinitiators:
4-Dimethylamino-4'-nitrobiphenyl is employed as a reagent in the production of photoinitiators, which are essential in the curing process of UV-curable materials. These photoinitiators play a crucial role in initiating the polymerization reaction when exposed to UV light.
Used in Organic Chemistry Reactions:
As a chemical intermediate, 4-Dimethylamino-4'-nitrobiphenyl is used in various organic chemistry reactions, contributing to the synthesis of a range of compounds for different applications across various industries.

InChI:InChI=1/C14H14N2O2/c1-15(2)13-7-3-11(4-8-13)12-5-9-14(10-6-12)16(17)18/h3-10H,1-2H3

Upstream product

• 1211-40-1 4-amino-4'-nitrobiphenyl 
• 77-78-1 dimethyl sulfate 
• 636-98-6 p-nitrobenzene iodide 
• 93296-10-7 (4-(dimethylamino)phenyl)zinc(II) chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 100-16-3 4-nitrophenylhydrazone 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 24067-17-2 4-nitrophenylboronic acid 
• 171364-83-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 28611-39-4 4-(dimethylamino)benzene-boronic acid 
• 586-78-7 para-nitrophenyl bromide 
• 171364-78-6 (4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 98878-74-1 bis-(4'-dimethylamino-biphenyl-4-yl)-diazene 

Relevant articles and documents

NOVEL HYDRAZONE DERIVATIVE WITH ARYL OR HETEROARYL GROUP SUBSTITUTED AT TERMINAL AMINE GROUP THEREOF AND USE THEREOF

The present invention relates to novel hydrazone derivatives in which a terminal amine group is substituted with an aryl group or a heteroaryl group, and uses thereof.

Novel hydrazone derivatives comprising aryl or heteroaryl group substituted at terminal amine and use thereof

The present invention relates to novel hydrazone derivatives with an aryl or heteroaryl group substituted at a terminal amine group thereof and a use thereof.

New Atglistatin closely related analogues: Synthesis and structure-activity relationship towards adipose triglyceride lipase inhibition

Adipose Triglyceride Lipase (ATGL) performs the first and rate-limiting step in lipolysis by hydrolyzing triacylglycerols stored in lipid droplets to diacylglycerols. By mediating lipolysis in adipose and non-adipose tissues, ATGL is a major regulator of

Highly efficient and magnetically recyclable graphene-supported Pd/Fe3O4 nanoparticle catalysts for Suzuki and Heck cross-coupling reactions

Herein, we report a facile and efficient one-step method for the synthesis of highly active, Pd/Fe3O4 nanoparticles supported on graphene nanosheets (Pd/Fe3O4/G) that exhibit excellent catalytic activity for Suzuki and Heck coupling reactions and that can be magnetically separated from the reaction mixture and recycled multiple times without loss of catalytic activity. The synthesis approach is based on the Microwave (MW)-assisted reduction of palladium and ferric nitrates in the presence of graphene oxide (GO) nanosheets using hydrazine hydrate as the reducing agent. The results provide a fundamental understanding of the system variables by comparing the catalytic activity and recyclability of four different catalysts with different properties. The most active and recyclable catalyst contains 7.6 wt% Pd nanoparticles with 4-6nm diameters in Pd(0) oxidation state well-dispersed with 30wt% Fe3O4 nanoparticles with 12-16 nm diameters on highly reduced GO containing a C/O ratio of 8.1. These combined properties produce remarkable catalytic activity for Suzuki cross coupling reactions under MW reaction conditions with an extremely high turnover number (TON) of 9250 and turn over frequency (TOF) of 111,000 h-1 at 80 °C. The magnetic properties imparted by the Fe3O4 component of the catalyst enables the catalyst to be easily isolated and recycled, thus greatly simplifying the ability to purify the reaction products and increasing the economic value of the catalyst. The utility of these magnetic catalysts towards Suzuki and Heck cross coupling reactions with a variety of functionalized substrates was also demonstrated.

Highly efficient and magnetically recyclable graphene-supported Pd/Fe3O4 nanoparticle catalysts for Suzuki and Heck cross-coupling reactions

Herein, we report a facile and efficient one-step method for the synthesis of highly active, Pd/Fe3O4 nanoparticles supported on graphene nanosheets (Pd/Fe3O4/G) that exhibit excellent catalytic activity for Suzuki and Heck coupling reactions and that can be magnetically separated from the reaction mixture and recycled multiple times without loss of catalytic activity. The synthesis approach is based on the Microwave (MW)-assisted reduction of palladium and ferric nitrates in the presence of graphene oxide (GO) nanosheets using hydrazine hydrate as the reducing agent. The results provide a fundamental understanding of the system variables by comparing the catalytic activity and recyclability of four different catalysts with different properties. The most active and recyclable catalyst contains 7.6 wt% Pd nanoparticles with 4-6 nm diameters in Pd(0) oxidation state well-dispersed with 30 wt% Fe3O4 nanoparticles with 12-16 nm diameters on highly reduced GO containing a C/O ratio of 8.1. These combined properties produce remarkable catalytic activity for Suzuki cross coupling reactions under MW reaction conditions with an extremely high turnover number (TON) of 9250 and turn over frequency (TOF) of 111,000 h-1 at 80°C. The magnetic properties imparted by the Fe3O4 component of the catalyst enables the catalyst to be easily isolated and recycled, thus greatly simplifying the ability to purify the reaction products and increasing the economic value of the catalyst. The utility of these magnetic catalysts towards Suzuki and Heck cross coupling reactions with a variety of functionalized substrates was also demonstrated.

Ortho-Phenylene oligomers with terminal push-pull substitution

ortho-Phenylenes are an emerging class of helical oligomers and polymers. We have synthesized a series of push-pull-substituted o-phenylene oligomers (dimethylamino/nitro) up to the octamer. Conformational analysis of the hexamer using a combination of low-temperature NMR spectroscopy and ab initio predictions of 1H NMR chemical shifts indicates that, like other o-phenylenes, they exist as compact helices in solution. However, the substituents are found to have a significant effect on their conformational behavior: the nitro-functionalized terminus is 3-fold more likely to twist out of the helix. Protonation of the dimethylamino group favors the helical conformer. UV/vis spectroscopy indicates that the direct charge-transfer interaction between the push-pull substituents attenuates quickly compared to other conjugated systems, with no significant charge-transfer band for oligomers longer than the trimer. On protonation of the dimethylamino group, significant bathochromic shifts with increasing oligomer length are observed: the effective conjugation length is 9 repeat units, more than twice that of the parent oligomer. This behavior may be rationalized through examination of the frontier molecular orbitals of these compounds, which exhibit greater delocalization after protonation, as shown by DFT calculations.

Microwave-assisted synthesis of palladium nanoparticles supported on graphene: A highly active and recyclable catalyst for carbon-carbon cross-coupling reactions

We have developed an efficient method to generate highly active Pd nanoparticles supported on graphene (Pd/G) by microwave-assisted chemical reduction of the corresponding aqueous mixture of a palladium salt and dispersed graphite oxide (GO) sheets. The Pd/G demonstrated excellent catalytic activity for the carbon-carbon cross-coupling reactions (Suzuki, and Heck) with a broad range of utility under ligand-free ambient conditions in an environmentally friendly solvent system. It also offers a remarkable turnover frequency (108,000 h-1) observed in the microwave-assisted Suzuki cross-coupling reactions with easy removal from the reaction mixture, recyclability with no loss of activity, and significantly better performance than the well-known commercial Pd/C catalyst. The catalyst was fully characterized by a variety of spectroscopic techniques including X-ray diffraction (XRD), Raman, TGA, electron microscopy (SEM, TEM), and X-ray photoelectron spectroscopy (XPS). The remarkable reactivity of the Pd/G catalyst toward Suzuki cross-coupling reactions is attributed to the high degree of the dispersion and concentration of Pd(0) nanoparticles supported on graphene sheets with small particle size of 7-9 nm due to an efficient microwave-assisted reduction method.

Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis

(Chemical equation presented) The coupling reaction of pinacolborane with various aryl bromides in the presence of a catalytic amount of Pd(OAc) 2 together with DPEphos as ligand and Et3N as base provided arylboronates. High yields were obtained in the case of electron-donor substituted aryl bromides. The direct preparation of arylboronates allowed the one-pot, two-step synthesis of unsymmetrical biaryls in high yields.

Efficient palladium-catalyzed synthesis of unsymmetrical donor-acceptor biaryls and polyaryls

4,4'-Unsymmetrically substituted biphenyls can be synthesized by cross-coupling reactions of substituted aromatic organometallic reagents and aromatic halides catalyzed by palladium complexes.This two-step method from commercially available aromatic halides has been used for the synthesis of a series of donor/acceptor para-substituted biphenyls, D-C6H4-C6H4-A, where D is an electron donor group and A an electron acceptor group, which are of interst as liquid crystal precursors and as having potential in non-linear optics.Biaryls in which the donor-phenyl moiety is replaced by a 2-furyl or 2-thienyl can be synthesized similarly.The method can also be used for the convergent synthesis of previously unreported unsymmetrically substituted polyparaphenylenes D-(C6H4)n-A (n = 3, 4).

ARYLATION OF AZULENE

In the reaction of azulene with phenylhydrazine and an oxidizing agent (Cu(2+)) a mixture of 1-phenylazulene (28percent) with 2-, 4-, and 6-phenylazulenes (27percent in total) is formed; a series of para-substituted phenylazulenes and α-naphthylazulenes were obtained in a similar way.If p-nitrophenylhydrazine is used, selective arylation of azulene (at position 1) and also of dimethylaniline (at the ortho and para positions) occurs.An excess of the oxidizing agent (Cu(2+)) increases and an excess of the reducing agent (arylhydrazine) reduces the selectivity of arylation.Some of the obtained arylazulenes can be used as dichroic coloring additives for liquid crystals.