1211-40-1

Basic information

• Product Name: 4-AMINO-4'-NITROBIPHENYL
• Synonyms: 4-(4-Nitrophenyl)aniline;4-Amino-4'-nitro-1,1'biphenyl;4-Nitro-4'-aminobiphenyl;4'-Nitrobiphenyl-4-amine;(4'-nitrobiphenyl-4-yl)amine;[4-(4-nitrophenyl)phenyl]amine;[4-(4-aminophenyl)phenyl]-dihydroxy-amine;4-(4-aminophenyl)-N,N-dihydroxyaniline
• CAS NO: 1211-40-1
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• Product Categories: Reagent for High-Performance Polymer Research;Biphenyls (for High-Performance Polymer Research);Functional Materials;Organic Nonlinear Optical Materials
• Mol File: 1211-40-1.mol

Chemical Properties

• Melting Point: 204°C
• Boiling Point: 354.35°C (rough estimate)
• Flash Point: 188.9 °C
• Appearance: /
• Density: 1.2042 (rough estimate)
• Refractive Index: 1.6660 (estimate)
• PKA: 3.69±0.10(Predicted)
• Stability: Stability
• CAS DataBase Reference: 4-AMINO-4'-NITROBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-4'-NITROBIPHENYL(1211-40-1)
• EPA Substance Registry System: 4-AMINO-4'-NITROBIPHENYL(1211-40-1)

Safety Data

• Statements: 20/21/22
• Safety Statements: 22-36/37/39
• RTECS: DV0350000
• HazardClass: IRRITANT
• Hazardous Substances Data: 1211-40-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
4-AMINO-4'-NITROBIPHENYL is used as a chemical intermediate for the production of dyes, pigments, and pharmaceuticals. Its unique chemical structure allows it to be a key component in the synthesis of various compounds with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-AMINO-4'-NITROBIPHENYL is used as a precursor in the synthesis of certain drugs. Its reactivity and functional groups make it a valuable building block for the development of new pharmaceutical compounds.
Used in Dye and Pigment Industry:
4-AMINO-4'-NITROBIPHENYL is used as a starting material in the production of dyes and pigments. Its ability to form various chemical bonds and its color properties make it suitable for creating a wide range of dyes and pigments used in different applications, such as textiles, plastics, and paints.

Upstream product

• 135-69-3 4-acetyl-4'-nitrobiphenyl 
• 586-78-7 para-nitrophenyl bromide 
• 1093736-99-2 9,10-dihydro-9,10-dimethyl-N-[4-(4-nitrophenyl)phenyl]-9,10-(epoxyimino)anthracene-11-carboxamide 
• 24067-17-2 4-nitrophenylboronic acid 
• 540-37-4 p-aminoiodobenzene 
• 82481-85-4 N-(4'-nitrobiphenyl-4-yl)benzamide 
• 92-93-3 1-phenyl-4-nitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 13924-28-2 N-benzylidene-4-phenylaniline 
• 1528-74-1 4,4'-dinitrobiphenyl 
• 7783-06-4 hydrogen sulfide 
• 51-84-3 acetylcholine 
• 7722-84-1 dihydrogen peroxide 
• 92-87-5 p,p'-diaminobiphenyl 

Downstream Products

• 114961-84-1 N-(4'-nitro-biphenyl-4-yl)-phthalamic acid 
• 84615-00-9 N-(4'-nitro-biphenyl-4-yl)-phthalimide 
• 91-22-5 quinoline 
• 92-87-5 p,p'-diaminobiphenyl 
• 1237534-14-3 3,4-dibromo-1-(4'-nitrobiphenyl-4-yl)-1H-pyrrole-2,5-dione 
• 372093-27-1 N-[4-(4-Nitrophenyl)phenyl)-(2-chloro-5-nitrophenyl)carboxamide 
• 838852-84-9 (3R)-N-(4'-Nitrobiphenyl-4-yl)quinuclidine-3-carboxamide hydrochloride 
• 2143-90-0 4-methoxy-4'-nitrobiphenyl 

Relevant articles and documents

Electroreductive generation of recyclable organic reductant from N,N′-dioctyl-4,4′-bipyridinium and Pd-catalyzed reductive coupling of aryl halides

Electroreduction of N,N′-dioctyl-4,4′-bipyridinium bis(triflimide) [C8V2+][Tf2N-] 2 in THF gave a dark blue solution of the corresponding quinoid C8V0, which worked as an efficient organic reductant for Pd-catalyzed reductive coupling of aryl bromides to give the corresponding biphenyl derivatives in good yields. After usual workup, [C8V 2+][Tf2N-]2 was recovered and reused for generation of the organic reductant C8V0. Georg Thieme Verlag Stuttgart.

Photochemical reactions of nitroso oxides at low temperatures: The first experimental evidence for dioxaziridines

Several singlet nitroso oxides (3a - e) were generated by the thermal reaction of triplet nitrenes (2a - e) with triplet oxygen at 95 K in 2-methyltetrahydrofuran. After photolysis of the nitroso oxides at 77 K using strong light intensities, the formation of intermediates was observed for the first time. From spectroscopic, kinetic, and chemical arguments, we postulate the formation of the following dioxaziridines: 4-(dioxaziridinyl)stilbene (4a), 4-(dioxaziridin-yl)-4′-nitrostilbene (4b), 4′-(dioxaziridin-yl)-4-(dimethylamino)stilbene (4c), 4′-(dioxaziridin-yl)-4-aminobiphenyl (4d), and 4-(dioxaziridin-yl)-4′-(nitrene-substituted)stilbene (4f). All dioxaziridines observed are highly reactive species. At 77 K, they react thermally to form the corresponding nitro compounds (5). The velocity of the ring opening reaction of the dioxaziridines (4 → 5) is not significantly influenced by substituents; the rate constants at 77 K are all equal to 0.0030 ± 0.0005 s-1. The transients were characterized by stationary UV/vis and/or ESR spectroscopy. Ab initio calculations of the thermal reaction of the nonsubstituted dioxaziridine (6) and N-phenyldioxaziridine (9) were performed. From this, it follows that dioxaziridines are experimentally observable species which are separated from the corresponding nitro products by an orbital symmetry-forbidden barrier.

Palladium(II) chloride/EDTA-catalyzed biaryl homo-coupling of aryl halides in aqueous medium in the presence of ascorbic acid

Both electron-deficient and electron-rich aryl bromides undergo biaryl homo-coupling in a basic aqueous-ethanolic medium in the presence of PdCl2-EDTA (1:1 molar ratio, 3 mol %) as catalyst and ascorbic acid as reductant (1 mol equiv) in acceptable to good yields.

Tetrakis(dimethylamino)ethylene (TDAE)-Pd promoted reductive homo-coupling of aryl halides

A combination of tetrakis(dimethylamino)ethylene (TDAE) and palladium catalysts promoted reductive homo-coupling of aryl halides efficiently to afford the corresponding biaryls in good to quantitative yields. TDAE acted as a very mild reductant, and easily reducible functional groups, such as a nitro formyl, ester, or nitrile group, remained unchanged.

Reductive coupling of aryl bromides using cat. Pd/TDAE system in ionic liquids

Pd/TDAE-promoted reductive coupling of aryl bromides (Ar-Br) proceeded in ionic liquids, e.g., BdmimBF4 and BdmimTf2N, to afford the corresponding symmetric biaryls (Ar-Ar) in good yields. Proper choice of ionic liquids and Pd catalysts is indispensable. Recycle use of BdmimTf2N and Pd catalyst was performed successfully. Copyright

Novel biphenyl tetrazole derivative and preparation method thereof

The invention relates to a novel biphenyl tetrazole derivative. A chemical general molecular formula of the novel biphenyl tetrazole derivative is shown as the accompanying drawing. The invention also relates to a preparation method of the novel biphenyl tetrazole derivative. A synthesis path is shown as the accompanying drawing, wherein n is selected from 0, 1, 2, 3, 4 and 5; Y is selected from -Br, -Cl, -NO2 and a substance shown as the accompanying drawing; R1, R2 and R3 are selected from -H, mono-substituted or poly-substituted -F, -(CH2)mCH3, -(CH2)mCF3, -O(CH2)mCH3, -O(CH2)mCF3 and -NO2 groups; m is selected from 0, 1, 2, 3, 4 and 5. The method comprises the operation steps that a compound II and 1,4-diazido dicyclic [2.2.2] octane are dissolved into a mixed reaction solution of a first organic solvent and carbon disulfide; filtering is performed to obtain yellow solids; after washing drying, the materials are dissolved into a second organic solvent; triphosgene or diphosgene is added; or phosgene reaction is performed; filtering is performed; filter liquid is collected; concentration is performed to obtain a crude product; the crude product is dissolved into a third organic solvent; ammonia water is added; concentration is performed to obtain yellow solid crude products; the solid crude products are dissolved into a four organic solvent; then, NaN3, I2 and organic amine NHpR are sequentially added into the organic solvent; basic water solution is added for quenching reaction; a fifth organic solvent is used for extracting the organic layer; concentration and purification are performed; a compound III is obtained.

Infrared irradiation or microwave assisted cross-coupling reactions using sulfur-containing ferrocenyl-palladacycles

The synthesis of four new sulfur-containing palladacycles 3a-d [FcC(S)OEtPdClZR3, where: 3a, ZR3: PPh3; 3b, ZR3: P(o-Tol)3; 3c, ZR3: PMe3; 3d, ZR3: SbPh3] from ferrocenyl thionoester 1 [FcC(S)OEt] in good yields is reported. The catalytic applications of these cyclopalladated complexes in Heck and Suzuki cross-coupling reactions were also evaluated, in combination with infrared or microwave as energy sources. The coupled products of these reactions were obtained in good to excellent yields, short reaction times and low catalyst loading.

WNT PATHWAY MODULATORS

The present invention relates to dihydropyrazolo[l,5-a]pyrimidine compounds of formula I, defined herein, as WNT pathways modulators, processes for making them, and pharmaceutical compositions comprising them. Methods of treatment of conditions mediated by WNT pathway signalling including cancer, fibrosis, stem cell and diabetic retinopathy, rheumatoid arthritis, psoriasis and myocardial infarction, comprising the compounds of formula I are also provided.

Variation of the backbone conjugation in NLO model compounds: Torsion-angle-restricted, biphenyl-based push-pull-systems

Terminal piperidinyl- and nitro-functionalized biphenyls, bridged between the 2 and. 2′ positions by a variable number of methylene groups, are synthesized and fully characterized. These push-pull systems with defined and restricted torsion angles between their phenyl rings are ideal model compounds to investigate the influence of the chromophore's conjugation in nonlinear optic (NLO) responses, A general synthetic route that can be implemented to access these model compounds is reported, starting from dibromo or ditriflate biphenyls. Hartwig-Buchwald cross-coupling, a selective azacycloalkylation of diaminobiphenyls and a mild oxidation of primary amines to nitro groups in the presence of a tertiary amine summarizes the synthetic pathway towards the desired model compounds. NLO properties of the series of torsionally constrained push-pull biphenyls are collected by electric-field-induced second-harmonic generation (EFISH) experiments. The results agree qualitatively with semi-empirical simulations based on the AM1 Hamiltonian. A. linear dependence of the quadratic response on the cos2(o) of the inter-aryl dihedral angle is observed, which points to oscillator strength loss as the dominant effect of increasing backbone twist

Photoactivatable HNO-releasing compounds using the retro-Diels-Alder reaction

We synthesized hetero-Diels-Alder cycloadducts from acyl nitroso derivatives and 9,10-dimethylanthracene, to be photo-inducible HNO-releasing agents and found that introduction of conjugated nitroaromatic groups effectively enhanced the responsiveness of HNO release to UV-A irradiation; we confirmed photoinduced HNO formation by EPR and GCMS analysis. The Royal Society of Chemistry.