100476-07-1

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 552-89-6 2-nitro-benzaldehyde 
• 100-66-3 methoxybenzene 
• 73376-03-1 (4-methoxyphenyl)(2-nitrophenyl)methanone 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 609-73-4 o-nitroiodobenzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 15290-22-9 o-(trimethylsilyl)nitrobenzene 

Downstream Products

• 479637-64-4 dichloro-acetic (4-methoxy-phenyl)-(2-nitro-phenyl)-methyl ester 
• 34999-53-6 (2-aminophenyl)-(4-methoxyphenyl)methanol 
• 179104-73-5 α-(4-Methoxyphenyl)-2-(N-trifluoroacetylamino)benzyl methyl ether 
• 179104-66-6 2-Amino-α-(4-methoxyphenyl)benzyl methyl ether 
• 73376-03-1 (4-methoxyphenyl)(2-nitrophenyl)methanone 
• 179104-55-3 α-(4-Methoxyphenyl)-2-nitrobenzyl methyl ether 

Relevant academic research and scientific papers

Synthesis of 1H-indazoles by reductive cyclization of o-nitro-ketoximes

ortho-Nitro-ketoximes are converted to 1H-indazoles upon reaction with carbon monoxide with [Cp*Fe(CO)2]2 as catalyst.

Phosphinite- and phosphite-based type I palladacycles as highly active catalysts for addition reactions of arylboronic acids with aldehydes, α,β-unsaturated ketones, α-ketoesters, and aldimines

Phosphinite- and phosphite-based type I palladacycle-catalyzed additions of arylboronic acids with aldehydes, α,β-unsaturated ketones, α-ketoesters, and aldimines are described. Our study showed that readily available phosphinite- and phosphite-based type I palladacycles could possess higher catalytic activity than phosphine-based palladacycles and were highly active, practical catalysts. Our study may pave the road for development of optically active phosphinite- and phosphite-based palladacycles for asymmetric catalysis.

Photo-Induced N-N Coupling of o-Nitrobenzyl Alcohols and Indolines to Give N-Aryl-1-amino Indoles

A novel method to synthesize N-aryl-1-amino indoles was established by the photoinduced N-N coupling reaction. This protocol is by treatment of o-nitrobenzyl alcohols and indolines in the presence of TEAI and acetic acid with a 24 W ultraviolet (UV) light

The cooperative effect of Lewis pairs in the Friedel-Crafts hydroxyalkylation reaction: A simple and effective route for the synthesis of (±)-carbinoxamine

An efficient C-C bond formation strategy between aromatic/heteroaromatic π-nucleophiles and Lewis acid activated aldehydes is described. This aromatic electrophilic substitution reaction of arenes or heteroarenes is facilitated by Lewis acid AlBr3. Aromatic rings with electron donating substituents are excellent nucleophilic counterparts in this reaction, generating carbinols in excellent yields (61-94%). The formation of triarylmethanes is also witnessed in the case of certain reactive aldehydes and aromatic π-nucleophiles through reactive carbocation formation. The formation of triarylmethane is reduced to a greater extent via retardation of the second π-nucleophile addition through a Lewis base, for example, pyridine, coordination with an aluminium alkoxide intermediate. Various aliphatic aldehydes also underwent Friedel-Crafts type hydroxyalkylation and generated the expected carbinols in moderate yields (41-53%) in the presence of AlBr3. This protocol has been successfully applied to the synthesize of the (±)-carbinoxamine, a therapeutically important histamine H1 antagonist, in a one-pot manner.

Friedel-Crafts hydroxyalkylation through activation of a carbonyl group using AlBr3: An easy access to pyridyl aryl/heteroaryl carbinols

Aromatic electrophilic substitution of aromatic/electron rich heteroaromatic compounds with AlBr3 activated aldehydes/ketone to afford pyridyl aryl/heteroaryl or diaryl carbinols is described. The strong electron donating group dictates the regiochemical outcome of the product.

Cascade synthesis of 3-quinolinecarboxylic ester via benzylation/ propargylation-cyclization

(Chemical Equation Presented) Reactions of 2-amino-aryl alcohols with β-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation- cyclization, 2-nitrophenyl propargyl alcohols with β-ketoesters catalyzed by FeCl3 and SnCl2 also produce the 4-alkyne-3- quinolinecarboxylic esters. The mechanistic details of this benzylation/ propargylation and cyclization cascade process are also discussed.

Cyclopalladated complexes catalyzed addition of arylboronic acids to aldehydes in neat water

Cyclopalladated ferrocenylimine complexes gave high yields for the addition of arylboronic acids with aldehydes in neat water using a weak acid as additive.

Novel photoacid generators for photodirected oligonucleotide synthesis

Photodirected oligonucleotide synthesis uses either direct or indirect light-dependent 5′-deprotection. Both have been reported to give lower stepwise synthetic yields than conventional methods. The deficiency appears to be due to incomplete deprotection at the oligonucleotide 5′-position and, additionally in the case where photodirection is indirect and uses photogenerated photoacid to effect 5′-detritylation, the depurinating effects of strong acid. We have developed novel photosensitive-2-nitrobenzyl esters that on irradiation with near UV light generate α-chloro-substituted acetic acids, such as trichloroacetic acid, which are widely and successfully used in conventional solid-phase oligonucleotide synthesis. α-Phenyl-4,5-dimethoxy-2-nitrobenzyltrichloroacetate and α-phenyl-4,5-dimethoxy-2,6-dinitrobenzyltrichloroacetate showed appropriate photochemical characteristics and were used for photodirected synthesis of a variety of oligonucleotides, including (T)5, TATAT, TGTGT, (T)10, (AT)5, (CT)5 (GT)5 and (TGCAT)2 on a modified Millipore Expedite DNA synthesizer. The outcomes were compared with those obtained by use of directly added trichloroacetic acid (conventional synthesis). The stepwise yields for the two methods were essentially identical.

Hydroxyalkylation, Acylation, Formylation, and Carboxylation of 2-Nitro- and 2-Chloro-1-(trimethylsilyl)benzene

The synthetic application of base-catalyzed carbodesilylation of aryltrimethylsilanes is demonstrated in the reactions of 2-nitro- (1a) and 2-chloro-1-(trimethylsilyl)benzene (1b) with aldehydes, ketones, acyl fluorides and carboxylic anhydrides, respectively, dimethylformamide, and carbon dioxide.The corresponding benzenes 3 and 8, (hydroxyalkyl)benzenes 4, 6, and 9, the benzophenones 12, the benzaldehydes 14, and the benzoic acids 17 are obtained in good yields.The new method is a useful alternative to the normal electrophilic substitution or the application of organometallic compounds, respectively, for the synthesis of polysubstituted benzenes.