14347-05-8

Basic information

• Product Name: 4-Benzyloxy-3-nitroacetophenone
• Synonyms: 4'-Benzyloxy-3'-nitroacetophenone;4-Benzyloxy-3-nitroacetophenone ,98%;Ethanone, 1-[3-nitro-4-(phenylMethoxy)phenyl]-;1-[4-PhenylMethoxy-3-nitrophenyl]ethanone;4-benzyloxy-3-nitroacetophenone, 1-[4-Phenylmethoxy-3-nitrophenyl]ethanone, 3-nitro-4-benzyloxyacetophenone, 1-(4-(benzyloxy)-3-nitrophenyl)ethan-1-one, 1-(4-(benzyloxy)-3-nitrophenyl)ethanone, 1-(4-benzyloxy-3-nitrophenyl)ethanone, 3-nitro-4-benzilossiacetofenone;4'-BENZYLOXY-3'-NITROACETOPHENONE;4-BENZYLOXY-3-NITRO-ACETOPHENONE;1-[3-nitro-4-(phenylmethoxy)phenyl]ethanone
• CAS NO: 14347-05-8
• Molecular Formula: C₁₅H₁₃NO₄
• Molecular Weight: 271.27
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);(intermediate of formoterol);Aromatics
• Mol File: 14347-05-8.mol

Chemical Properties

• Melting Point: 134-136 °C(Solv: acetone (67-64-1))
• Boiling Point: 426.6 °C at 760 mmHg
• Flash Point: 184.6 °C
• Appearance: yellow solid
• Density: 1.247 g/cm₃
• Vapor Pressure: 1.75E-07mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Chloroform, DMF, DMSO, Ethyl Acetate
• CAS DataBase Reference: 4-Benzyloxy-3-nitroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Benzyloxy-3-nitroacetophenone(14347-05-8)
• EPA Substance Registry System: 4-Benzyloxy-3-nitroacetophenone(14347-05-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 14347-05-8(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C15H13NO4/c1-11(17)13-7-8-15(14(9-13)16(18)19)20-10-12-5-3-2-4-6-12/h2-9H,10H2,1H3

Upstream product

• 54696-05-8 4'-benzyloxy-acetophenone 
• 515152-69-9 2-benzyloxy-5-vinylnitrobenzene 
• 99-93-4 4-Hydroxyacetophenone 
• 6322-56-1 4'-hydroxy-3'-nitroacetophenone 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 400-93-1 3-nitro-4-fluoroacetophenone 
• 100-51-6 benzyl alcohol 

Downstream Products

• 193761-53-4 (S)-1-(4-(benzyloxy)-3-nitrophenyl)-2-bromoethanol 
• 1122063-33-5 (1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-ol 
• 306966-56-3 N-(2-(benzyloxy)-5-((S)-2-bromo-1-hydroxyethyl)phenyl)formamide 
• 1361398-83-5 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 
• 1361398-82-4 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 
• 1361398-81-3 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)hexyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 
• 1361398-80-2 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)pentyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 
• 1361398-79-9 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 
• 1361398-78-8 N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)ethyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide 
• 1361398-77-7 N-(5-(2-(benzyl(2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)hexyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide 
• 1361398-76-6 N-(5-(2-(benzyl(2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)pentyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide 
• 1361398-75-5 N-(5-(2-(benzyl(2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide 
• 1361398-74-4 N-(5-(2-(benzyl(2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)ethyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide 
• 201677-59-0 N-[5-((1R)-2-bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]carboxamide 

Relevant articles and documents

An Intermediate in the Synthesis of Formoterol

In the title compound, 4-benzyloxy-3-nitrophenacyl bromide, C15H12BrNO4, the two planar nitrophenyl and benzyloxy groups are inclined at a dihedral angle of 17.1(1) deg.The NO2 group is twisted out of the plane of the phenyl ring by 20.4(3) deg to minimize steric hindrance between O(4) and O(3); the O(4)...O(3) separation is 2.600(5) Angstroem and the angle O(4)...O(3)-N(1) is 88.2(4) deg.

2-(3-Benzyloxy-4-nitrophenyl)oxirane, an Intermediate in the Synthesis of Formoterol

In the title compound, C15H13NO4, the two planar nitrophenyl and benzyloxy groups are inclined at 152.3(2) deg.The torsion angle about the central C-O bond is 177.5(5) deg, giving an extended C-C-O-C chain.The nitro group is twisted out of the plane of the phenyl ring by 28.4(3) deg to diminish steric hindrance; O atoms of the nitro and benzyloxy groups are separated by only 2.625(7) Angstroem.The dihedral angles between the epoxy ring and the two aromatic rings are 98.3(3) and 102.6(3) deg.There is a possible C-H...O intermolecular interaction.

Dichloroacetophenones targeting at pyruvate dehydrogenase kinase 1 with improved selectivity and antiproliferative activity: Synthesis and structure-activity relationships

Dichloroacetophenone is a pyruvate dehydrogenase kinase 1 (PDK1) inhibitor with suboptimal kinase selectivity. Herein, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones. Structure-activity relationship analyses (SARs) enabled us to identify three potent compounds, namely 54, 55, and 64, which inhibited PDK1 function, activated pyruvate dehydrogenase complex, and reduced the proliferation of NCI-H1975 cells. Mitochondrial bioenergetics assay suggested that 54, 55, and 64 enhanced the oxidative phosphorylation in cancer cells, which might contribute to the observed anti-proliferation effects. Collectively, these results suggested that 54, 55, and 64 could be promising compounds for the development of potent PDK1 inhibitors.

Preparation method of 3-nitro-4-benzyloxy-2-bromoacetophenone

The invention relates to a preparation method of 3-nitro-4-benzyloxy-2-bromoacetophenone. Particularly, 3-nitro-4-hydroxyacetophenone and benzyl bromide are taken as raw materials, and 3-nitro-4-benzyloxy-2-bromoacetophenone is synthesized through hydroxy protection and trimethylphenylammonium tribromide bromination reaction in a high-yield manner. The preparation method of 3-nitro-4-benzyloxy-2-bromoacetophenone in the synthesis route is high in yield, low in cost, easy to operate and suitable for industrialization.

Method forsynthesizing ketone by oxidation of alkene under catalysis of iron

The invention discloses a method for synthesizing ketoneby oxidation of alkene under catalysis of iron, and belongs to the field of catalyzed synthesis technologies and fine chemical synthesis. According to the specific method, air or oxygen is taken as an oxidizing agent under the acceleration action ofhydrosilaneand a ketone compound is synthesized byoxidation of alkene under catalysis of iron. The method has the advantages that the catalyst is wide in source, cheap and environment-friendly; the oxidant is wide in source and cheap and does not generate a waste; the reaction conditions are mild, the selectivity is high and the yield is high;a substrate is wide and stable; a functional group of the substrate is good in compatibility and the application range of the substrate is wide; and alkene molecules can be well converted into the ketone. The separation yield of a target product reaches 98% under the optimized reaction conditions.

COMPOUNDS, IN PARTICULAR FOR USE IN THE TREATMENT OF A DISEASE OR CONDITION FOR WHICH A BROMODOMAIN INHIBITOR IS INDICATED

The invention relates to a compound for use in the treatment of a disease or condition for which a bromodomain inhibitor is indicated characterized by a general formula (1) and a compound according to formula (3).

Benzylether fumaric acid luck not Trow an important intermediate for the synthesis of compound

The invention discloses a synthetic method of a formoterol fumarate important intermediate benzyl ether compound. The synthetic method comprises the following steps: enabling a compound I to react with a compound II in an organic solvent at 100-120 DEG C for 4-6 hours under the concerted catalysis of a catalyst (I) and a catalyst (II); and by using an inorganic alkaline substance as an acid-binding agent in the reaction process, after the reaction ends, adding water to perform cooling and crystallization, and filtering to obtain the benzyl ether compound. The synthetic steps disclosed by the invention perform concerted catalysis on benzyl etherification reaction between a substitute and benzyl chloride by adopting the two catalysts at the same time, and can be used for increasing the reaction speed, shortening the reaction time, shortening the total reaction time to 4 hours from 48 hours, and greatly improving the production efficiency; and after the reaction ends, the qualified benzyl ether compound (of which the content is more than 98%) can be obtained without refining; the synthetic method disclosed by the invention is more suitable for the large-scale industrial production of formoterol fumarate.

Design, synthesis and evaluation of dual pharmacology β2- adrenoceptor agonists and PDE4 inhibitors

A novel series of formoterol-phthalazinone hybrids were synthesised and evaluated as dual pharmacology β2-adrenoceptor agonists and PDE4 inhibitors. Most of the hybrids displayed high β2-adrenoceptor agonist and moderate PDE4 inhibitory activities. The most potent compound, (R,R)-11c, exhibited agonist (EC50 = 1.05 nM, pEC50 = 9.0) and potent PDE4B2 inhibitory activities (IC50 = 0.092 μM).

Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of asthma and COPD

We designed and synthesized a novel class of dual pharmacology bronchodilators targeting both b2-adrenoceptor and PDE4 by applying a multivalent approach. The most potent dual pharmacology molecule, compound 29, possessed good inhibitory activity on PDE4B2 (IC50 = 0.278 μM, which was more potent than phthalazinone, IC50 = 0.520 lM) and possessed excellent relaxant effects on tracheal rings precontracted by histamine (pEC50 = 9.3).

Development of an enabling route to PF-00610355: A novel inhaled β2-adrenoreceptor agonist

The initial route used to prepare PF-00610355 (8) for early clinical development is described. Through careful choice of solvent, an efficient, telescoped route to carboxylic acid 23 was developed, affording this late-stage intermediate in 80% yield over 4 steps. Deprotection of 23 to give sodium salt 24a and coupling with amine 6·HCl afforded the desired API. Effective synthetic routes to two of the starting materials, chiral bromide 1 and amine 6, are also described.