4836-66-2

Usage

Uses

Used in Chemical Synthesis:
2,4-Dinitrobenzyl alcohol 97 is used as a reagent in chemical synthesis for its ability to participate in various chemical reactions, contributing to the production of different compounds and materials.
Used in Nitric Oxide Biochemistry Research:
As a tool in biochemical research, 2,4-dinitrobenzyl alcohol 97 is used for studying nitric oxide due to its capacity to release this molecule upon exposure to ultraviolet light, which aids in understanding the role and behavior of nitric oxide in biological systems.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2,4-dinitrobenzyl alcohol 97 is used as a key intermediate in the synthesis of various drugs, leveraging its chemical properties to create therapeutic agents.
Used in Performance Materials:
2,4-Dinitrobenzyl alcohol 97 is also utilized in the development of performance materials, where its unique characteristics can enhance the properties of the final products.
Used in Laboratory Safety:
Given its potential explosive nature, 2,4-dinitrobenzyl alcohol 97 is used as a case study in laboratory safety training to educate researchers on the proper handling and storage of hazardous compounds.

InChI:InChI=1/C7H6N2O5/c10-4-5-1-2-6(8(11)12)3-7(5)9(13)14/h1-3,10H,4H2

Upstream product

• 29024-77-9 2,4-dinitrobenzyl acetate 
• 100-51-6 benzyl alcohol 
• 619-73-8 4-nitrobenzyl chloride 
• 610-30-0 2,4-dinitrobenzoic acid 
• 3013-38-5 2,4-dinitrobenzyl bromide 
• 123-72-8 butyraldehyde 
• 100-44-7 benzyl chloride 
• 610-57-1 2,4-dinitrobenzyl chloride 
• 121-14-2 2,4-dinitrotoluene 
• 528-75-6 2,4-dinitrobenzaldehyde 

Downstream Products

• 84955-59-9 Phosphoric acid 2-chloro-phenyl ester 2,4-dinitro-benzyl ester (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(9-phenyl-9H-xanthen-9-yloxymethyl)-tetrahydro-furan-3-yl ester 
• 3013-38-5 2,4-dinitrobenzyl bromide 
• 528-75-6 2,4-dinitrobenzaldehyde 
• 102170-39-8 4-amino-2-nitrobenzaldehyde 
• 610-30-0 2,4-dinitrobenzoic acid 
• 1500090-76-5 2,4-dinitrobenzylidene diacetate 
• 29024-77-9 2,4-dinitrobenzyl acetate 
• 22996-20-9 4-iodo-2-nitrobenzyl alcohol 
• 22996-19-6 (4-bromo-2-nitrophenyl)methanol 
• 22996-18-5 (4-chloro-2-nitrophenyl)methanol 
• 213548-42-6 2'-O-[1-(2,4-dinitrobenzyloxy)ethyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 202577-48-8 Methyl 1-O-2,4-dinitrobenzyl-β-D-glucopyranuronate 
• 213547-89-8 2,4-dinitrobenzyl vinyl ether 
• 202577-46-6 Methyl 2,3,4-tri-O-acetyl-1-O-2,4-dinitrobenzyl-β-D-glucopyranuronate 

Relevant academic research and scientific papers

2-((3,5-Dinitrobenzyl)thio)quinazolinones: Potent Antimycobacterial Agents Activated by Deazaflavin (F420)-Dependent Nitroreductase (Ddn)

Swapping the substituents in positions 2 and 4 of the previously synthesized but yet undisclosed 5-cyano-4-(methylthio)-2-arylpyrimidin-6-ones 4, ring closure, and further optimization led to the identification of the potent antitubercular 2-thio-substituted quinazolinone 26. Structure-activity relationship (SAR) studies indicated a crucial role for both meta-nitro substituents for antitubercular activity, while the introduction of polar substituents on the quinazolinone core allowed reduction of bovine serum albumin (BSA) binding (63c, 63d). While most of the tested quinazolinones exhibited no cytotoxicity against MRC-5, the most potent compound 26 was found to be mutagenic via the Ames test. This analogue exhibited moderate inhibitory potency against Mycobacterium tuberculosis thymidylate kinase, the target of the 3-cyanopyridones that lies at the basis of the current analogues, indicating that the whole-cell antimycobacterial activity of the present S-substituted thioquinazolinones is likely due to modulation of alternative or additional targets. Diminished antimycobacterial activity was observed against mutants affected in cofactor F420 biosynthesis (fbiC), cofactor reduction (fgd), or deazaflavin-dependent nitroreductase activity (rv3547), indicating that reductive activation of the 3,5-dinitrobenzyl analogues is key to antimycobacterial activity.

KB3H8: An environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols

Selective reduction of aldehydes and ketones to their corresponding alcohols with KB3H8, an air- and moisture-stable, nontoxic, and easy-to-handle reagent, in water and THF has been explored under an air atmosphere for the first time. Control experiments illustrated the good selectivity of KB3H8 over NaBH4 for the reduction of 4-acetylbenzaldehyde and aromatic keto esters. This journal is

Metal–Organic Framework-Encapsulated CoCu Nanoparticles for the Selective Transfer Hydrogenation of Nitrobenzaldehydes: Engineering Active Armor by the Half-Way Injection Method

A novel armor-type composite of metal–organic framework (MOF)-encapsulated CoCu nanoparticles with a Fe3O4 core (Fe3O4@SiO2-NH2-CoCu@UiO-66) has been designed and synthesized by the half-way injection method, which successfully serves as an efficient and recyclable catalyst for the selective transfer hydrogenation. In this half-way injection approach, the pre-synthetic Fe3O4@SiO2-NH2-CoCu was injected into the UiO-66 precursor solution halfway through the MOF budding period. The formed MOF armor could play a role of providing significant additional catalytic sites besides CoCu nanoparticles, protecting CoCu nanoparticles, and improving the catalyst stability, thus facilitating the selective transfer hydrogenation of nitrobenzaldehydes into corresponding nitrobenzyl alcohols in high selectivity (99 %) and conversion (99 %) rather than nitro group reduction products. Notably, this method achieves the precise assembly of a MOF-encapsulated composite, and the ingenious combination of MOF and nanoparticles exhibits excellent catalytic performance in the selective hydrogen transfer reaction, implementing a “1+1>2” strategy in catalysis.

Dual copper- and photoredox-catalysed C(sp2)-C(sp3) coupling

The use of copper catalysis with visible light photoredox catalysis in a cooperative fashion has recently emerged as a versatile means of developing new C-C bond forming reactions. In this work, dual copper and photoredox catalysis is exploited to effect C(sp2)-C(sp3) cross-couplings between aryl boronic acids and benzyl bromides.

Laccase-Mediator System for Alcohol Oxidation to Carbonyls or Carboxylic Acids: Toward a Sustainable Synthesis of Profens

By combining two green and efficient catalysts, such as the commercially available enzyme laccase from Trametes versicolor and the stable free radical 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), the oxidation in water of some primary alcohols to the corresponding carboxylic acids or aldehydes and of selected secondary alcohols to ketones can be accomplished. The range of applicability of bio-oxidation is widened by applying the optimized protocol to the oxidation of enantiomerically pure 2-arylpropanols (profenols) into the corresponding 2-arylpropionic acids (profens), in high yields and with complete retention of configuration.

Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes

Asymmetric catalytic variants of sunlight-driven photochemical processes hold extraordinary potential for the sustainable preparation of chiral molecules. However, the involvement of short-lived electronically excited states inherent to any photochemical reaction makes it challenging for a chiral catalyst to dictate the stereochemistry of the products. Here, we report that readily available chiral organic catalysts, with well-known utility in thermal asymmetric processes, can also confer a high level of stereocontrol in synthetically relevant intermolecular carbon-carbon bond-forming reactions driven by visible light. A unique mechanism of catalysis is proposed, wherein the catalyst is involved actively in both the photochemical activation of the substrates (by inducing the transient formation of chiral electron donor-acceptor complexes) and the stereoselectivity-defining event. We use this approach to enable transformations that are extremely difficult under thermal conditions, such as the asymmetric α-alkylation of aldehydes with alkyl halides, the formation of all-carbon quaternary stereocentres and the control of remote stereochemistry.

Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

Chemoselective reduction of various carbonyl compounds to alcohols with ammonia borane (AB), a nontoxic, environmentally benign, and easily handled reagent, in neat water was achieved in quantitative conversions and high isolated yields. Interestingly, α- and β-keto esters were selectively reduced to corresponding hydroxyl esters by AB, while diols were obtained when sodium borohydride was used as a reducing agent. The procedure is also compatible with the presence of a variety of base-labile protecting groups, such as tosyl, acetyl, benzoyl, ester groups, and acid-labile protecting groups such as trityl and TBDMS groups, and others, such as the unsaturated double bond, nitro and cyano groups. Finally, a kilo scale reaction of methyl benzoylformate with AB was conducted in water and gave methyl mandelate in 94% yield.

Nitrobenzyl monates antibacterial compounds

Compounds of formula (II): STR1 wherein Y is --CH=CH--CH2 --CH-- or STR2 R1 is hydrogen or C1-4 alkyl, R2 is hydrogen or C1-6 alkyl, R3 is hydrogen, nitro or C1-6 alkyl and, when