5840-41-5

Usage

Nitroaromatic compound

A type of aromatic compound containing a nitro group (-NO2) attached to a benzene ring.

Benzene ring

A six-carbon ring structure with alternating single and double bonds, forming the backbone of many organic compounds.

Nitro group

A functional group consisting of an oxygen atom double-bonded to a nitrogen atom (-NO2), which is known for its high electronegativity and reactivity.

Benzyl group

A functional group derived from a benzene ring with a single carbon-carbon bond to an alkyl chain, in this case, a single carbon (methyl) group.

Organic synthesis

A chemical process used to create new organic compounds by combining simpler molecules.

Intermediate

A temporary compound formed during a multi-step chemical reaction, which is used to produce the final product.

Pharmaceuticals

Medications or drugs used in the treatment, cure, prevention, or diagnosis of diseases.

Dyes

Chemical substances used to color fabrics, materials, or other substances.

Pesticides

Chemicals used to control, repel, or kill pests, including insects, weeds, and fungi.

Pale yellow solid

A physical description of the compound's appearance, indicating a pale yellow color and solid state at room temperature.

Insoluble in water

The compound does not dissolve in water, making it immiscible with aqueous solutions.

Soluble in organic solvents

The compound dissolves easily in organic solvents, such as alcohols, ethers, and hydrocarbons.

Safety precautions

Necessary measures taken to minimize the risk of accidents, exposure, or harm when handling and storing hazardous materials, such as 1-Benzyl-3-nitrobenzene.

Upstream product

• 101-81-5 Diphenylmethane 
• 3958-57-4 1-bromomethyl-3-nitrobenzene 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 
• 619-25-0 3-Nitrobenzyl alcohol 
• 13331-27-6 m-nitrobenzene boronic acid 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 619-23-8 3-Nitrobenzyl chloride 
• 98-80-6 phenylboronic acid 
• 13326-10-8 benzyl methyl carbonate 
• 884-90-2 benzyl diethyl phosphate 
• 960-16-7 tributylphenylstannane 
• 55095-33-5 (3-nitrophenyl)phenylmethanol 

Downstream Products

• 61424-26-8 3-benzylaniline 
• 63021-27-2 acetic acid-(3-benzyl-anilide) 
• 1058345-46-2 2,2,2-trichloroethyl 3-nitrobenzhydrylcarbamate 
• 2243-80-3 3-nitrobenzophenone 
• 3002-33-3 4-(3'-nitrobenzyl)-nitrobenzene 

Relevant academic research and scientific papers

Synthetic method of diarylmethanes

The invention discloses a synthetic method of diarylmethanes. The method is characterized in that benzyl pseudohalide and aromatic boric acid are reacted in an organic solvent under alkaline condition. The method employs easily available raw materials, conversion is realized under effect of no transition metal catalysis, water-free and oxygen-free are not required, Lewis acid catalysis is not required, the method has wide substrate universality, and various substituted diarylmethanes can be synthesized by the method.

Coupling of arylboronic acids with benzyl halides or mesylates without adding transition metal catalysts

We report herein a transition-metal-free coupling reaction of arylboronic acids with benzyl halides and mesylates for the construction of C(sp2)[sbnd]C(sp3) bonds. A unique feature of this coupling reaction is the formation regioisomers in some cases. Mechanistic studies suggest that this reaction may proceed via an unprecedented Friedel–Crafts-type reaction pathway under base conditions with the assistance of boronic acid moiety.

Synthesis of diarylmethanes through palladium-catalyzed coupling of benzylic phosphates with arylsilanes

An efficient approach to the benzylation of arenes has been developed. The reactions described provide straightforward access to diarylmethanes through Pd-catalyzed coupling of benzylic phosphates with arylsilanes in good to excellent yields. The reaction tolerates a wide range of functionalities such as halide, alkoxyl, and nitro groups.

Suzuki-miyaura cross-couplings mediated by trans-PdBr(N-Succ)(PPh 3)2: A convenient synthetic method for diarylmethanes and aryl(heteroaryl)- methanes

Diarylmethanes can be accessed efficiently by Suzuki-Miyaura cross-couplings of arylboronic acids with benzyl halides mediated by trans-PdBr(N-Succ) (PPh3)2. The methodology can be applied to the synthesis of aryl(heteroaryl)methanes. Georg Thieme Verlag Stuttgart New York.

One-pot dual substitutions of bromobenzyl chloride, 2-chloromethyl-6- halogenoimidazo[1,2-a]pyridine and -[1,2-b]pyridazine by Suzuki-Miyaura cross-coupling reactions

A very simple, mild and inexpensive palladium-catalyzed cross-coupling of (hetero)arylboronic acids with benzylic halides occurs in good yield. This method was successfully expanded to two heterocyclic electrophiles and allowed onepot dual substitutions of bromobenzyl chloride, 2-chloromethyl-6- halogenoimidazo[1,2-a]pyridine or -[1,2-b]pyridazine, leading to numerous new unsymmetrical methylenelinked biaryl systems. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

N-tosyloxycarbamates as reagents in rhodium-catalyzed C-H amination reactions

Metal nitrenes for use in C-H insertion reactions were obtained from N-tosyloxycarbamates in the presence of an inorganic base and a rhodium(II) dimer complex catalyst. The C-H amination reaction proceeds smoothly, and the potassium tosylate that forms as a byproduct is easily removed by filtration or an aqueous workup. This new methodology allows the amination of ethereal, benzylic, tertiary, secondary, and even primary C-H bonds. The intramolecular reaction provides an interesting route to various substituted oxazolidinones, whereas the intermolecular reaction gives trichloroethoxycarbonyl-protected amines that can be isolated with moderate to excellent yields and that cleave easily to produce the corresponding free amine. The development, scope, and limitations of the reactions are discussed herein. Isotopic effects and the electronic nature of the transition state are used to discuss the mechanism of the reaction.

Simple palladium(II) precatalyst for suzuki-miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners

trans-PdBr(N-Succ)(PPh3)2 (1) is a universally effective precatalyst for Suzuki-Miyaura cross-couplings of benzylic halides with aryl- or heteroarylboronic acids. Substituted aryl halides and halogenated cyclic enones can be cross-coupled with aryl- or vinylboronic acids in excellent yields. Catalyst recycling is also demonstrated.

Suzuki-miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates

(Chemical Equation Presented) The palladium-catalyzed cross-coupling of potassium aryltrifluoroborates with benzylic halides occurs in good yield with high functional group tolerance. The increased stability of potassium aryltrifluoroborates compared to other boron coupling partners makes this an effective route to functionalized methylene-linked biaryl systems.

Air-stable, phosphine-free anionic palladacyclopentadienyl catalysts: Remarkable halide and pseudohalide effects in Stille coupling

The Stille cross-coupling of allylic and benzyl bromides is shown to proceed efficiently using phosphine-free dinuclear anionic palladacyclopentadienyl catalysts possessing bridging (N,O)-imidate ligands. The type of bridging anion influences the catalytic activity considerably. Halide anions such as chloride, bromide or iodide also influence the catalytic activity but to a far lesser extent than the pseudohalide imidate anions (from succinimide or phthalimide). A Baldwin-type cooperative effect is seen with 7a using CuI as a co-catalyst, in the presence of two equivalents of CsF in DMF at 40°C. In toluene, these additives slow down substrate turnover. Wiley-VCH Verlag GmbH & Co. KGaA.

Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids

(Chemical Equation Presented) Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids was investigated. Optimum conditions employed the simple catalytic system of palladium(II) acetate (1 mol %) and triphenylphosphine (4 mol %) with either potassium phosphate or potassium carbonate as the base and toluene as the solvent at 90°C. Using the developed conditions, a series of structurally diverse diarylmethanes were prepared.