19479-80-2

Usage

Uses

Used in Organic Synthesis:
1-(diazomethyl)-4-nitrobenzene is used as a reagent for forming new carbon-carbon bonds in the field of organic synthesis. Its application is primarily due to its ability to facilitate reactions that result in the creation of these essential structural components in organic molecules.
Used in Diazomethyl Group Introduction:
In the chemical industry, 1-(diazomethyl)-4-nitrobenzene is utilized as a reagent for the introduction of the diazomethyl group into various organic molecules. The diazomethyl group is a valuable functional group that can be used to modify the properties of organic compounds, making this application crucial for the synthesis of a wide range of molecules with specific characteristics.
Used in Research and Development:
1-(diazomethyl)-4-nitrobenzene is also employed in the research and development sector, where its reactivity and unique functional groups make it a valuable tool for exploring new chemical reactions and synthesizing novel compounds. Its use in this context aids in the advancement of knowledge and innovation within the field of organic chemistry.

InChI:InChI=1/C7H5N3O2/c8-9-5-6-1-3-7(4-2-6)10(11)12/h1-5H

Upstream product

• 6310-10-7 4-nitrobenzaldehyde hydrazone 
• 1747-50-8 4-methyl-N'-[(4-nitrophenyl)methylidene]benzene-1-sulfonohydrazide 
• 16286-94-5 C₁₆H₁₇N₃O₄S 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 63927-15-1 4-[2,2-dimethyl-4-(4-nitro-phenyl)-1,1-dioxo-1λ⁶-thietan-3-yl]-morpholine 
• 63927-17-3 4-{6-[(4-nitro-phenyl)-methanesulfonyl]-cyclohex-1-enyl}-morpholine 
• 57832-83-4 (6R)-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2,3-dicarboxylic acid 2-benzhydryl ester 3-(4-nitro-benzyl) ester 
• 67216-72-2 1-nitro-4-(ethoxymethyl)benzene 
• 67807-58-3 (S)-2-((1S)-3-benzyl-7-oxo-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-mercapto-3-methyl-butyric acid 4-nitro-benzyl ester 
• 67807-61-8 (S)-3-mercapto-3-methyl-2-((1S)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-butyric acid 4-nitro-benzyl ester 
• 82820-05-1 C₁₅H₁₀N₄O₄ 
• 89543-11-3 5,5-Dimethyl-7-(4-nitro-phenyl)-1,5-dihydro-[1,2]diazepin-4-one 
• 89543-00-0 6,6-Dimethyl-4-(4-nitro-phenyl)-2,3-diaza-bicyclo[3.2.0]hept-2-en-7-one 
• 99557-41-2 3-hydroxy-4-(4-nitrophenyl)quinolin-2(1H)-one 
• 619-93-2 4,4'-dinitro stilbene 
• 121829-54-7 (1S,4S,5R,6R,7S)-6,7-Dichloro-4-(4-nitro-phenyl)-2,3-diaza-bicyclo[3.2.0]hept-2-ene 
• 38332-15-9 3-Methyl-4-(p-nitrophenyl)-but-1-en 
• 38332-18-2 5-(p-Nitrophenyl)-cis-pent-2-en 

Relevant academic research and scientific papers

A Transition-Metal-Free and Base-Mediated Carbene Insertion into Sulfur-Sulfur and Selenium-Selenium Bonds: An Easy Access to Thio- and Selenoacetals

A transition-metal-free and base-mediated carbene insertion across sulfur-sulfur and selenium-selenium bonds has been developed by employing N-tosylhydrazone as a stable and safe carbene precursor. The ylide formation from carbene followed by Stevens rearrangement are considered to be the key steps. This thiol and selenol-free protocol delivers thioacetals and selenoacetals in good to excellent yields in short reaction time with good functional group tolerance. A one-pot synthesis involving in situ generation of tosylhydrazone has also been demonstrated. (Figure presented.).

Continuous Flow Synthesis and Purification of Aryldiazomethanes through Hydrazone Fragmentation

Electron-rich diazo compounds, such as aryldiazomethanes, are powerful reagents for the synthesis of complex structures, but the risks associated with their toxicity and instability often limit their use. Flow chemistry techniques make these issues avoidable, as the hazardous intermediate can be used as it is produced, avoiding accumulation and handling. Unfortunately, the produced stream is often contaminated with other reagents and by-products, making it incompatible with many applications, especially in catalysis. Herein is reported a metal-free continuous flow method for the production of aryldiazomethane solutions in a non-coordinating solvent from easily prepared, bench-stable sulfonylhydrazones. All by-products are removed by an in-line aqueous wash, leaving a clean, base-free diazo stream. Three successful sensitive metal-catalyzed transformations demonstrated the value of the method.

Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones

We report a denitrogenative dihalogenation reaction of phenyldiazomethanes in which the hypervalent iodine reagents PhICl2 and TolIF2 act as surrogates for elemental chlorine and fluorine. Halogen transfer from iodane to aryldiazomethane is described, as is a tandem oxidative dihalogenation reaction between iodane and hydrazone. This is the first use of non-α-stabilized diazo compounds in this reaction, which provided an efficient synthesis of aryldifluoromethane (ArCHF2) and aryldichloromethane (ArCHCl2) derivatives. (Figure presented.).

Method for labeling and fragmenting DNA

The invention relates to a method for labeling and fragmenting a single- or double-stranded deoxyribonucleic acid (DNA) comprising the following steps: chemically fragmenting the DNA by creating at least one abasic site on said DNA, attaching a marker to at least one of the fragments by means of a labeling reagent, said reagent covalently and predominantly coupling to at least one phosphate of said fragment. The invention finds a preferred application in the field of diagnosis.

Advantageous Syntheses of Diazo Compounds by Oxidation of Hydrazones with Lead Tetraacetate in Basic Environments

Varied sensitive diazo compounds 3 are produced efficiently and safely in 3-6 g quantities by oxidation (eq 1) of hydrazones 1 at -78 deg C with lead tetraacetate (2) in triethylamine/chloroform, N-methylmorpholine/dimethylformamide, tetramethylguanidine (8)/dimethylformamide, and tetramethylguanidine/methylene chloride, respectively, upon use of appropriate workup and handling techniques.New and improved nonhazardous procedures have been developed for preparing and handling hydrazones 1 from aldehydes and ketones in reactions with excess hydrazine.

Amino acyl cephalosporin derivatives

Antibacterial cephalosporin compounds of the Formula (I): STR1 wherein W is a pharmaceutically acceptable salt or a carboxyl-protecting group; n is an integer from 1 to 2; --X-- is --X1 -- where the X1 moieties are the same or different and selected from the group consisting of (D) or (L) STR2 Y is --O--; wherein R1 is selected from the group consisting of: STR3 R2 is H, --CH2 R4, --CHR52 or --CR53, wherein R4 is H, F, Cl, Br, --OH, --CN, STR4 --CH(CH3)2, --CH2 (OH), STR5 or --C CH, where Q1, Q2 and Q3 are the same or different and selected from the group consisting of H, F, Cl or Br; R5 is F, Cl or Br; and Z1 is H or an amino protecting group.

THE SYNTHESIS OF ARYL DIAZOMETHANES

A convenient and rapid method for preparing aryldiazomethanes from the related tosylhydrazones employing phase transfer catalysis with hydrocarbon solvents in good to excellent yields has been developed.

A CONVENIENT SYNTHESIS OF DIAZO COMPOUNDS BY CATALYTIC DEHYDROGENATION OF HYDRAZONES WITH COBALT SCHIFF BASE COMPLEX-OXYGEN SYSTEM

Cobalt Schiff base complex catalyzed oxidation of hydrazones is found to be a convenient method for the synthesis of diazo compounds.