94-22-4

Usage

InChI:InChI=1/C10H11NO4/c1-2-7-15-10(12)8-3-5-9(6-4-8)11(13)14/h3-6H,2,7H2,1H3

Upstream product

• 71-23-8 propan-1-ol 
• 122-04-3 4-nitro-benzoyl chloride 
• 62-23-7 4-nitro-benzoic acid 
• 764-02-3 1-diazopropane 
• 923-99-9 tri-n-propyl phosphite 
• 555-21-5 4-Nitrophenylacetonitrile 
• 96953-69-4 p-nitrobenzoic-p-toluenesulfonic anhydride 
• 540-54-5 1-Chloropropane 
• 106-94-5 propyl bromide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 140613-96-3 N-methyl-N-(2-hydroxyethyl)-4-nitrobenzamide 
• 619-73-8 4-nitrobenzyl chloride 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 857488-86-9 N-benzoyl-N'-(4-nitro-benzoyl)-guanidine 
• 3166-06-1 (4-amino-benzoyl)-guanidine 
• 94-12-2 risocaine 
• 3166-02-7 (4-nitro-benzoyl)-guanidine 

Relevant academic research and scientific papers

Vitamin B1-catalyzed aerobic oxidative esterification of aromatic aldehydes with alcohols

A straightforward aerobic oxidative esterification of aryl aldehydes with alcohols has been developed for the synthesis of substituted esters by employing vitamin B1 as a cost-effective, metal-free, and eco-friendly NHC catalyst. Air is used as a green terminal oxidant. The reaction is a useful addition to the existing NHC-catalytic oxidative esterification.

N-Heterocyclic Carbene Catalyzed Ester Synthesis from Organic Halides through Incorporation of Oxygen Atoms from Air

Oxygenation reactions with molecular oxygen (O2) as the oxygen source provides a green and straightforward strategy for the construction of O-containing compounds. Demonstrated here is a novel N-heterocyclic carbene (NHC) catalyzed oxidative transformation of simple and readily available organic halides into valuable esters through the incorporation of O-atoms from O2. Mechanistic studies prove that the deoxy Breslow intermediate generated in situ is oxidized to a Breslow intermediate for further transformation by this oxidative protocol. This method broadens the field of NHC catalysis and promotes oxygenation reactions with O2.

DBU-Based Dicationic Ionic Liquids Promoted Esterification Reaction of Carboxylic Acid with Primary Chloroalkane Under Mild Conditions

Abstract: A series of DBU-based (DBU = 1, 8-diazabicyclo [5.4.0] undec-7-ene) dicationic ionic liquids with different anions were successfully synthesized by the reaction of DBU and 1, 6-dichlorohexane. Therein, the dicationic ionic liquid 1, 1′-(hexane-1, 6-diyl)bis(1, 8-diazabicyclo [5.4.0]undec-7-enium) dichlorine (IL-1) was successfully employed as an efficient catalyst in esterification reaction of carboxylic acids with primary chloroalkanes under mild conditions without any additional basic reagents. Moreover, the optimum catalyst could be efficiently reused for five times without any significant change on the catalytic effect. The improved protocol is not only efficient, but also green and pollution-free.

Zinc-Catalyzed Esterification of N-β-Hydroxyethylamides: Removal of Directing Groups under Mild Conditions

Amide transformations involving C–N bond cleavage are recognized as difficult reactions owing to the inert nature of amides resulting from resonance. Accordingly, a strong inductive effect and geometrical distortion reasonably decrease the resonance stabilization to attenuate the C–N linkage. Although the conversion of such activated amides has been studied intensively, reaction systems for “unactivated” amides are underdeveloped. We herein report that a zinc(II) trifluoromethanesulfonate [Zn(OTf)2] catalyst achieves the esterification of a wide range of unactivated tertiary amides with the assistance of intramolecular acyl rearrangement. The reaction was applied to the one-pot removal of various amide-based directing groups under mild reaction conditions to afford the corresponding esters in high yields.

ZnII and CdII MOFs based on an amidoisophthalic acid ligand: Synthesis, structure and catalytic application in transesterification

Solvothermal reaction of zinc(ii) and cadmium(ii) salts with 5-propionamidoisophthalic acid (H2L1) and 5-benzamidoisophthalic acid (H2L2) in the presence or absence of an auxiliary ligand gives rise to a series of 1D, 2D and 3D Zn(ii) or Cd(ii) self-assembled metal-organic frameworks as revealed by X-ray diffraction structural analyses: [Zn(μ-L1-μ-1κOO′:2κO′′)(formamide)2]n (1), [{Zn2(μ-L1-1κO:2κO′)2(4,4′-bipyridine)2(H2O)}·2(DMF)·5(H2O)]n (2), [Cd(μ-L1-μ-1κO2O′:2κO′′2O′′′)(DMF)]n (3), [{Zn(μ-L2-1κO:2κO′)(4,4′-bipyridine)(H2O)}·(H2O)]n (4) and [{Cd(μ-L2-μ-1κO2O′:2κO′′2O′′′)(formamide)(4,4′-bipyridine)}·(formamide)]n (5), which are also characterized by elemental analysis, IR spectroscopy and thermogravimetric analysis. The different architectures found in 1-5 result from the coordination modes of the carboxylate groups, which can assume nonbridging monodentate (in 1, 2 and 4), bridging bidentate (also in 1), bridging chelate (in 3 and 5) and chelate bidentate (also in 5) coordination. While 1 and 5 possess one dimensional double chain type structures, 3 has a 1D cyclic type structure and 2 and 4 have 2D or 3D wave-like structures, respectively. Topological analysis has shown that 1 and 5 have a 3-connected uninodal net with a topological type SP1-periodic net, 2 has a 2,4-connected binodal net, 3 has a 4-connected uninodal net structure and 4 has a more complex 2,2,2,4-connected tetranodal net. Frameworks 1-5 act as heterogeneous catalysts for the transesterification reaction of different carboxylate esters, with 4 showing the highest activity. These heterogeneous catalysts can be recycled without losing activity.

Ultrasound assisted direct oxidative esterification of aldehydes and alcohols using graphite oxide and Oxone

A sonochemical procedure for direct oxidative esterification of aldehydes and alcohols using graphite oxide and Oxone in an alcoholic solvent is described. Mild reaction conditions, short reaction times, cost-effectiveness, and facile isolation of the products make the present system as a practical method.

Base-free oxidation of alcohols to esters at room temperature and atmospheric conditions using nanoscale Co-based catalysts

The direct oxidation of alcohols to esters with molecular oxygen is an attractive and crucial process for the synthesis of fine chemicals. To date, the heterogeneous catalyst systems that have been identified are based on noble metals or have required the addition of base additives. Here, we show that Co nanoparticles embedded in nitrogen-doped graphite catalyze the aerobic oxidation of alcohols to esters at room temperature under base-free and atmospheric conditions. Our Co@C-N catalytic system features a broad substrate scope for aromatic and aliphatic alcohols as well as diols, giving their corresponding esters in good to excellent yields. This apparently environmentally benign process provides a new strategy with which to achieve selective oxidation of alcohols.

An efficient one-pot oxidative esterification of aldehydes to carboxylic esters using B(C6F5)3-TBHP

A simple and efficient protocol for oxidative esterification of diverse aldehydes with alcohols was accomplished with tert-butyl hydroperoxide and 1 mol % of tris(pentafluorophenyl)borane [B(C6F5)3] to generate the corresponding esters in good to excellent yields. The present protocol represents compatibility with wide range of functional groups as well as exceptional tolerance toward acid labile protecting groups such as TBDPS, TBDMS, acetonide, and Boc.

Oxidation of benzaldehydes to benzoate esters using household bleach and sodium iodide in alcohol solvents

Various substituted benzaldehydes were converted into benzoate esters with household bleach and sodium iodide in an alcohol solvent. The reaction works best with methanol. Only 4-chlorobenzaldehyde, 3-nitrobenzaldehyde, and 4-nitrobenzaldehyde reacted completely with 1-propanol under these conditions. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright

Inclusion complex containing epoxy resin composition for semiconductor encapsulation

The invention is an epoxy resin composition for sealing a semiconductor, including (A) an epoxy resin and (B) a clathrate complex. The clathrate complex is one of (b1) an aromatic carboxylic acid compound, and (b2) at least one imidazole compound represented by formula (II): wherein R2 represents a hydrogen atom, C1-C10 alkyl group, phenyl group, benzyl group or cyanoethyl group, and R3 to R5 represent a hydrogen atom, nitro group, halogen atom, C1-C20 alkyl group, phenyl group, benzyl group, hydroxymethyl group or C1-C20 acyl group. The composition has improved storage stability, retains flowability when sealing, and achieves an effective curing rate applicable for sealing delicate semiconductors.