2929-91-1

Usage

Uses

Used in Organic Synthesis:
P-NITROBENZAL DIACETATE is used as an intermediate in the synthesis of various organic compounds due to its reactivity and ability to form derivatives that are useful in the production of different chemical products.
Used in Perfume Production:
P-NITROBENZAL DIACETATE is used as a key component in the creation of perfumes, where its chemical properties contribute to the development of unique and complex fragrances.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, P-NITROBENZAL DIACETATE is utilized as a precursor in the synthesis of various drugs, highlighting its importance in the development of new medications.
Used as a Reagent in Chemical Reactions:
P-NITROBENZAL DIACETATE is employed as a versatile reagent, particularly in the acetylation of alcohols and amines, where it facilitates specific chemical transformations that are essential in the synthesis of target compounds.
Safety Considerations:
Due to its hazardous nature, P-NITROBENZAL DIACETATE should be handled with caution. It can cause irritation to the skin, eyes, and respiratory system, necessitating proper safety measures during its use and storage.

InChI:InChI=1/C11H11NO6/c1-7(13)17-11(18-8(2)14)9-3-5-10(6-4-9)12(15)16/h3-6,11H,1-2H3

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 108-24-7 acetic anhydride 
• 854180-22-6 (4-nitro-phenyl)-(toluene-4-sulfonyl)-methanol 
• 555-16-8 4-nitrobenzaldehdye 
• 100-52-7 benzaldehyde 
• 581-55-5 benzylidene 1,1-diacetate 
• 98-86-2 acetophenone 
• 116287-27-5 6-(4-Nitro-phenyl)-6,7-dihydro-5H-5,7,7a,13-tetraaza-benzo[3,4]cyclohepta[1,2-b]naphthalen-8-one 
• 86119-84-8 phosphoric acid 
• 7697-37-2 nitric acid 
• 611-73-4 Benzoylformic acid 
• 104769-61-1 methyl 9-oxo-1,2,3,9-tetrahydropyrrolo[2,1-b]-quinazoline-1-carboxylate 
• 104-53-0 3-phenyl-propionaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 619-72-7 4-nitrobenzonitrile 
• 134895-40-2 (+/-)-O-acetyl-p-nitromandelonitrile 
• 24588-74-7 4-nitrophenyl-1,3-dithiane 
• 41159-02-8 2-(4-nitrophenyl)-1,3-dithiolane 
• 123371-45-9 ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate 
• 911287-47-3 (4-nitrophenyl)methylene 1,1'-bis(2-methylpropanoate) 
• 1360860-06-5 (4-nitrophenyl)methylene 1,1'-dipentanoate 
• 1360860-08-7 (4-nitrophenyl)methylene 1,1'-dibutyrate 
• 29197-16-8 3-(4-nitrobenzylidene)pentane-2,4-dione 
• 140-11-4 Benzyl acetate 
• 555-16-8 4-nitrobenzaldehdye 
• 171860-01-8 diethyl 2-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)malonate 
• 14506-32-2 1-(4-nitrophenyl)but-3-en-1-ol 
• 1014-23-9 5-(4-nitrophenyl)oxazole 

Relevant academic research and scientific papers

The studies on chemoselective promiscuous activity of hydrolases on acylals transformations

Chemoselective, mild and convenient protocol for the hydrolysis of the synthetically relevant acylals via promiscuous enzyme-catalyzed hydrolysis has been developed. It has been shown that promiscuous activity of the used hydrolases dominates their native activity related with carboxylic esters hydrolysis. The main advantage of the present methodology is that it can be conducted under neutral conditions at room temperature. Moreover, complete deprotection of acylals takes place within 10–20 min. Developed protocol can be used with compounds having a variety of hydrolytic labile groups since the cleavage is proceeded under neutral conditions and occurs exclusively on acylal moiety. Further this protocol was extended by the tandem Passerini multicomponent reaction leading to the α-acetoxy amides using acylals as the surrogates of the carbonyl components to P-MCR.

Acylation of Phenols, Alcohols, Thiols, Amines and Aldehydes Using Sulfonic Acid Functionalized Hyper-Cross-Linked Poly(2-naphthol) as a Solid Acid Catalyst

Abstract: The hyper-cross-linked porous poly(2-naphthol) fabricated by the Friedel–Crafts alkylation of 2-naphthol has been functionalized with sulfonic acid to obtain a solid acid catalyst. The catalyst is applied for the protection of phenol, alcohols, thiols, amines and aldehydes with acetic anhydride at room temperature. The catalytic protection using the new solid acid is featured by achieving high yield at neat condition, needing no aqueous work-up and/or chromatographic separation, and showing excellent recycling efficiency, suggesting the potential of this sulfonated porous polymers as a new protection protocol in a wide range of sustainable chemical reactions. Graphical Abstract: [Figure not available: see fulltext.].

N-Propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) as a green and reusable heterogeneous nanocatalyst for the chemoselective preparation and deprotection of acylals

Abstract: N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) was simply synthesized and used as a highly efficient, environmentally friendly, and chemoselective catalyst for the synthesis of 1,1-diacetates (acylals) from the one-pot condensation reaction of various aromatic aldehydes with acetic anhydride, in high yield of products (86–96%) and short reaction time (20–60?min) under solvent-free conditions at room temperature. In addition to these results, we further studied the possibility of deprotection of the resulting acylals into benzaldehyde derivatives in this catalytic system by the addition of water. More importantly, noteworthy advantages of this study are non-use of toxic organic solvents and catalysts, simple work-up procedure, short reaction time, high yield of products, and recovery and reusability of MNPs-PSA by an external magnet. Graphical Abstract: A simple and highly efficient procedure for the protection of various aldehydes with acetic anhydride in the presence of N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) is reported. We further studied the possibility of deprotection of the resulting acylals into benzaldehyde derivatives in this catalytic system by the addition of water as a green solvent. The catalyst was reused several times without loss of its catalytic activity.

SiO2@FeSO4 nano composite as nanocatalyst for the green synthesis 1,1-diacetates from aldehydes under solvent-free conditions

Aldehydes compounds selective converted to 1,1-diacetates as protective reagent with SiO2@FeSO4 nano composite as effective nano catalyst at room temperature under solvent-free condition and acetic anhydride (Ac2O) as acet

Tungstosulfonic acid as an efficient solid acid catalyst for acylal synthesis for the protection of the aldehydic carbonyl group

Tungstosulfonic acid (TSA) has been found to be an efficient solid acid catalyst for the protection of aldehydic carbonyl groups by geminal diacetate (acylal) formation following the nucleophilic addition of acetic anhydride under neat conditions as well as in a solvent. The TSA catalyst is fully characterized by infrared spectroscopy, wide-angle X-ray scattering analysis, and scanning electron microscopy with energy dispersive X-ray spectroscopy. The deprotection of acylals to corresponding aldehydes has also been investigated under the similar conditions. The catalyst can be reused seven times without a significant loss of activity. In addition, no chromatographic separations are needed to obtain the desired products. This method is a green approach for the chemoselective protection of aldehydes in the presence of ketones.

Microwave-assisted green synthesis of 1,1-diacetates (acylals) using selectfluor as an environmental-friendly catalyst under solvent-free conditions

An efficient and simple procedure has been developed for the acetylation of aldehyde by selectfluor [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate)] as a chemoselective and environmentally friendly catalyst under solvent-free conditions or microwave irradiation. The application of microwave irradiation improved the yields and reduced the reaction times. In this study, selective conversion of aldehydes was observed in the presence of ketones, and the deprotection of 1,1-diacetates has also been achieved using selectfluor in water as green solvent in reflux conditions. The methodology provides synergy of microwave irradiation which offers several advantages such the simple work-up procedure, short reaction time, excellent yields and environmentally benign procedure.

Preparation of 1,1-diacetates from aldehydes by LiBH4 and Ac2O in the presence of cation exchange resin

A variety of 1,1-diacetates have been produced from the corresponding aldehydes (1 mmol) by LiBH4(1.25 mmol) and Ac2O (1 mL) in the presence of DOWEX(R)50WX4 (0.5 g) as a cation exchange resinwithin 10 min at room temperature with excellent yields of the products (93-97%).

Solvent-free Chemoselective Synthesis of 1,1-diacetates Catalyzed by Iron Zirconium Phosphate

In the present study, a mild, rapid, and efficient method for the protection of aldehydes with acetic anhydride (AA) in the presence of iron zirconium phosphate (ZPFe), at room temperature is reported. Selective conversion of aldehydes was observed in the presence of ketones. Under these conditions, different aldehydes bearing electron-withdrawing and electron-donating substituents were reacted with AA and the corresponding 1,1-diacetates (acylals) were obtained in high to excellent yields. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions. Also, the deprotection of 1,1-diacetates has been achieved using this catalyst in water. The catalyst was characterized by several physico-chemical techniques. It was recovered easily from the reaction mixture, regenerated, and reused at least 7 times without significant loss in catalytic activity. This protocol has the advantages of easy availability, stability, reusability of the eco-friendly catalyst, chemoselectivity, simple experimental and work-up procedure, solvent-free conditions and only a stoichiometric amount of AA is needed.

Zinc zirconium phosphate as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions

In the present study, a mild, rapid, and efficient method for the protection of aldehydes with acetic anhydride (AA) in the presence of zinc zirconium phosphate (ZPZn) as a nano catalyst, at room temperature is reported. Selective conversion of aldehydes was observed in the presence of ketones. Under these conditions, different aldehydes bearing electron-withdrawing and electron-donating substituents were reacted with AA and the corresponding 1,1-diacetates (acylals) were obtained in high to excellent yields. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions. Also, the deprotection of 1,1-diacetates has been achieved using this catalyst in water. This nanocatalyst was characterized by several physico-chemical techniques. It was recovered easily from the reaction mixture, regenerated and reused at least 7 times without significant loss in catalytic activity. This protocol has the advantages of easy availability, stability, reusability of the eco-friendliness, chemoselectivity, simple experimental and work-up procedure, solvent-free conditions and usage of only a stoichiometric amount of AA.

Formation of benzylidenes-diacetates catalyzed by activated zeolite "LZY-562" and clay (K10/ZnCl2): An unexpected functional selectivity

Activated zeolites LZY-562 and clay montmorillonite K10 at room temperature without solvent catalyzes the synthesis of benzylidenesdiacetates from carbonyl compounds. A chemoselectivity was observed between aldehydes and ketones, between the different aldehydes and ketones as well.