4735-49-3

Usage

Chemical group

Nitro compounds

Physical state

Yellowish crystal

Molecular weight

199.21 g/mol

Uses

Precursor in the synthesis of dyes, pigments, and pharmaceuticals

Photochemical properties

Can undergo photochemical reactions

Applications

Photolithography processes, optical and electronic devices

Hazardous nature

Potentially toxic and irritating effects, should be handled with care

InChI:InChI=1/C12H9NO2/c14-13(15)9-8-11-6-3-5-10-4-1-2-7-12(10)11/h1-9H/b9-8+

Upstream product

• 75-52-5 nitromethane 
• 66-77-3 1-naphthaldehyde 
• 39221-01-7 1-(naphthalen-1-yl)-2-nitroethan-1-ol 
• 826-74-4 1-vinylnaphthalene 
• 1127-76-0 1-ethylnapthelene 
• 98978-43-9 (E)-ethyl 3-(naphthalen-1-yl)acrylate 
• 13026-12-5 (E)-3-(naphthalen-1-yl)acrylic acid 
• 3163-27-7 2-(bromomethyl)naphthalene 
• 90-12-0 1-Methylnaphthalene 

Downstream Products

• 37709-92-5 3-Naphthalen-1-yl-4-nitro-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester 
• 1268482-47-8 C₂₀H₂₀N₂O₂ 
• 1361018-74-7 (1R,2R,3R,4S,5R,6S)-tert-butyl 2-benzyl-1-hydroxy-3,5-di(naphthalen-1-yl)-4,6-dinitrocyclohexanecarboxylate 
• 1354655-50-7 2-fluoro-3-(naphthalen-1-yl)-4-nitro-1-phenyl-2-(phenylsulfonyl)butan-1-one 
• 1416889-80-9 (2S,3R)-1-(dimethyl(phenyl)silyl)-3-(naphthalen-1-yl)-4-nitro-2-phenylbutan-1-one 
• 1416890-04-4 (2S,3R)-2-(3,4-dimethoxyphenyl)-1-(dimethyl(phenyl)silyl)-3-(naphthalen-1-yl)-4-nitrobutan-1-one 
• 1416133-03-3 4-fluoro-4-(1-(naphthalen-1-yl)-2-nitroethyl)-3-phenylisoxazol-5(4H)-one 
• 1457935-45-3 (2R,3S)-N-methyl-3-(naphthalen-1-yl)-4-nitro-2-phenylbutanamide 

Relevant academic research and scientific papers

A Molecular Iodine-Mediated Synthesis of Cyclopenta[c]furo[3,2-b]furan-5,6-diones: Assembly of an Angular Dioxatriquinane Core

A molecular iodine-mediated synthesis of angular oxatriqinane core from 3-acetyl-2H-chromen-2-ones, β-bromo-β-nitrostyrenes, and pyridine in the presence of Et3N in MeCN containing a trace amount of water was developed. The reaction proceeds via intermolecular Michael reaction of 2-oxo-2-(2-oxo-2H-chromen-3-yl)-1-(pyridin-1-ium-1-yl)ethan-1-ide with bromonitrostyrene followed by intramolecular Michael reaction and elimination steps. Evidence for the stereochemistry of a typical product is obtained from single-crystal X-ray analyses. The important feature of this strategy is the fact that it forms three stereogenic centers with good selectivity.

Skeletally Tunable Seven-Membered-Ring Fused Pyrroles

We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible parameters and substrate adaptations. These rare 7-mrFPs are now accessible on a millimolar scale, and selected examples exhibit high antioxidant activity.

Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"

We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.

Method for preparing nitroolefin from aryl ethane and nitrate

According to the method, aryl ethane and nitrate, which are cheap and easy to obtain, are used as raw materials, and the E-nitroolefin compound is synthesized through a dehydrogenation nitration reaction of copper/silver catalyzed aryl ethane under the ox

Preparation method of beta-trans-nitroolefin

The invention relates to a preparation method of beta-trans-nitroolefin. The method comprises: sequentially adding an olefin compound, a nitration reagent and a solvent into a reaction container, mixing the substances uniformly, and carrying out constant temperature reaction for 18h under an illumination condition to obtain a reaction solution; and sequentially carrying out drying, concentration and column chromatography treatment on the reaction solution to obtain the beta-trans-nitroolefin compound. The method is simple and practicable, low in cost and high in product yield, can realize large-scale production, and has good industrial application prospects in the aspects of functional organic material, bioactive compound and drug synthesis.

A photocatalyst-free photo-induced denitroalkylation of β-nitrostyrenes with 4-alkyl substituted Hantzsch esters at room temperature

A photocatalyst-free stereoselectively photo-induced strategy for the denitroalkylation of β-nitrostyrenes using 4-alkyl substituted Hantzsch esters as the alkyl source under xenon lamp irradiation is developed. The reaction proceeds at room temperature and affords the corresponding products in moderate to excellent yields. The oxidant di-t-butyl peroxide serves as an efficient radical initiator under irradiation of a Xenon lamp, initiating alkyl radicals from the 4-alkyl substituted Hantzsch esters.

Facile Synthesis of 1,3,5-Triarylbenzenes and 4-Aryl-NH-1,2,3-Triazoles Using Mesoporous Pd-MCM-41 as Reusable Catalyst

We report mesoporous nano-Pd-MCM-41 catalyzed rapid and efficient synthesis of 1,3,5-triarylbenzenes via de-nitrative cyclotrimerization of β-nitrostyrenes. All the reactions were very fast and high yielding. The Pd-MCM-41 was also very effective in catalyzing de-nitrative [3+2] cycloaddition of β-nitrostyrenes with TMSN3 to synthesize 4-aryl-NH-1,2,3-triazoles. The catalyst was reused at least up to eight times with minimum loss of catalytic activity.

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations

Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.

Catalytic and Mechanistic Developments of the Nickel(II) Pincer Complex-Catalyzed Hydroarsination Reaction

Synthetic challenges have significantly slowed the development of the catalytic asymmetric hydroarsination reaction despite it being a highly attractive C?As bond formation methodology. In addition, there is a poor understanding of the main reaction steps in such reactions which limit further development in the field. Herein, key intermediates of the hydroarsination reaction catalyzed by a PCP NiII-Cl pincer complex are presented upon investigating the reaction with DFT calculations, conductivity measurements, NMR spectroscopy, and catalytic screening. The novel Ni–Cl–As interaction proposed was then contrasted against known NiII-catalyzed hydrophosphination reactions to highlight dissimilarities between them even though P and As share a close group relationship. Lastly, the asymmetric hydroarsination of nitroolefins was further developed to furnish a library of chiral organoarsines in up to 99 % yield and 80 % ee under mild conditions (?20 °C to RT) between 5 to 210 mins.

A chiral bicyclic skeleton-tethered bipyridine-Zn(OTf)2 complex as a Lewis acid: Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes

A conformationally rigid chiral bicyclic skeleton tethered bipyridine-Zn(OTf)2 complex facilitated the enantioselective Friedel-Crafts alkylation of indoles with trans-β-nitroarylalkenes in an enantioselective manner at elevated temperature. Indoles reacted smoothly with β-nitroarylalkenes to generate the corresponding 3-(2-nitroalkyl)indoles in good to excellent yields (up to 94%) with moderate to excellent enantioselectivities (up to 91%). The stereochemical outcome of the product from indole and trans-β-nitrostyrene in the presence of the CRCB tethered bipyridine-Zn(OTf)2 complex and the DFT calculation of the CRCB tethered bipyridine-Zn:trans-β-nitrostyrene complex support the si-face attack of indole on trans-β-nitrostyrene.