4096-88-2

Basic information

• Product Name: 1-Azido-2,4-dinitrobenzene
• Synonyms: 1-Azido-2,4-dinitrobenzene;2,4-dinitrophenyl azide
• CAS NO: 4096-88-2
• Molecular Formula: C₆H₃N₅O₄
• Molecular Weight: 0
• Mol File: 4096-88-2.mol
• Article Data: 28

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 1-Azido-2,4-dinitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azido-2,4-dinitrobenzene(4096-88-2)
• EPA Substance Registry System: 1-Azido-2,4-dinitrobenzene(4096-88-2)

Safety Data

• Hazardous Substances Data: 4096-88-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 5091, 1987 DOI: 10.1016/S0040-4039(00)95598-9

InChI:InChI=1/C6H4N5O4/c7-9-8-5-2-1-4(10(12)13)3-6(5)11(14)15/h1-3,7H/q+1

Upstream product

• 584-48-5 2,4-dinitrobromobenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 970-88-7 2,4-dinitrophenyl benzenesulfonate 
• 742-25-6 2,4-dinitrophenyl 4-methylbenzenesulfonate 
• 154853-46-0 2,4-dinitrophenyl 4-methoxybenzenesulfonate 
• 2363-36-2 (2,4-dinitro-phenyl)-(4-nitro-phenyl)-ether 
• 97-02-9 2,4-Dinitroanilin 
• 794-65-0 1-(4-formylphenoxy)-2,4-dinitrobenzene 
• 32101-47-6 1-(4-cyanophenoxy)-2,4-dinitrobenzene 
• 798-96-9 4-(2,4-dinitro-phenoxy)-benzoic acid methyl ester 
• 2363-38-4 1-(m-chlorophenoxy)-2,4-dinitrobenzene 
• 2548-96-1 1-(4-chlorophenoxy)-2,4-dinitrobenzene 
• 2486-07-9 2,4-dinitrophenyl phenyl ether 

Downstream Products

• 51824-71-6 2,4-dinitrophenylimino(triphenyl)phosphorane 
• 117693-87-5 4-Methoxycarbonyl-5-methyl-1-(o,p-dinitrophenyl)-1,2,3-triazole 
• 51-28-5 2,4-Dinitrophenol 
• 97-02-9 2,4-Dinitroanilin 
• 20762-60-1 potassium azide 
• 100-67-4 potassium phenolate 
• 18772-11-7 5-nitro-2,1,3-benzoxadiazole 
• 117694-01-6 1-(o,p-dinitrophenyl)-4-methoxycarbonyl1,2,3-triazole-5-carbaldehyde p-tosylhydrazone 
• 117693-98-8 1-(o,p-dinitrophenyl)-5-formyl-4-methoxycarbonyl-1,2,3-triazole 
• 2217-55-2 bis(2,4-dinitrophenyl) disulphide 
• 2253-67-0 bis-(2,4-dinitro-phenyl)-sulfide 
• 117693-96-6 5-Azidomethyl-1-(o,p-dinitrophenyl)-4-methoxycarbonyl-1,2,3-triazole 
• 106410-64-4 4-[N-(2,4-dinitro-phenyl)-heptanimidoyl]-morpholine 
• 98252-30-3 4-[N-(2,4-dinitro-phenyl)-cyclopentanecarboximidoyl]-morpholine 

Relevant articles and documents

Metallacycle-catalyzed SNAr reaction in water: Supramolecular inhibition by means of host-guest complexation

The performance of a PtII diazapyrenium-based metallacycle as a reusable substoichiometric catalyst for the SNAr reaction between halodinitrobenzenes and sodium azide at rt in aqueous media is reported. The results suggest that the c

Thiophenol-formaldehyde triazole causes apoptosis induction in ovary cancer cells and prevents tumor growth formation in mice model

In the present study a library of thiophenol-formaldehyde-triazole (TFT) derivatives was synthesized and screened against CAOV3, CAOV4 and ES-2 ovary cancer cell lines. Initial screening revealed that five-compounds 5a, 5b, 5j, 5h and 5i inhibited the viability of tested cell lines. Analysis of apoptosis revealed that increase in compound 5a (most active) concentration from 0.25 to 2.0 μM enhanced apoptotic cell proportion. Transwell assay showed reduction in invasive potential of CAOV3 cells on treatment with compound 5a. In wound healing assay increasing the concentration of compound 5a from 0.5 to 2.0 μM caused a significant (P 0.05) decrease in the migration potential. Western blotting showed that compound 5a treatment markedly decreased the level of matrix metalloproteinase (MMP)-2 and ?9 in CAOV3 cells. Treatment of CAOV3 cells with compound 5a caused a marked decrease in Focal Adhesion Kinase (FAK) activation. Tumor growth was inhibited in the compound 5a treated mice markedly than those of untreated group. The tumor metastasis to liver, intestine, spleen and peritoneal cavity was markedly decreased in mice treated with 10 mg/kg dose of compound 5a. Examination of Von Willebrand factor (vWF) expression in liver, intestinal and pulmonary lesions showed a marked decrease in the compound 5a-treated mice. The infiltration of macrophages in the metastatic lesions showed a significant decrease in compound 5a-treated mice. In conclusion, the compound 5a inhibited ovary cancer cell viability and induced apoptosis through decrease in expression of vWF and metalloproteinase, suppression of FAK activation and decrease in infiltration of macrophages. The compound 5a therefore can be investigated further for the treatment of ovary cancer.

Kinetic study on SNAr reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes with Azide ion: Effect of changing nucleophile from hydroxide to Azide ion on reaction mechanism and reactivity

Second-order rate constants (kN3-) for SNAr reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes (2a-2h) with (Formula presented.) in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C have been measured spectrophotometrically. The Bronsted-type plot is linear with β1g=-0.38. The Hammett plots correlated with (Formula presented.) constants exhibit highly scattered points. In contrast, the Yukawa-Tsuno plot results in an excellent linear correlation with ρY = 1.02 and r = 0.51, indicating that a negative charge develops partially on the O atom of the leaving Y-substituted-phenoxy moiety in the transition state. Accordingly, the reactions have been concluded to proceed through a stepwise mechanism, in which expulsion of the leaving group occurs in the rate-determining step. Comparison of kN3- with the kOH- values reported previously for the corresponding reactions with OH has revealed that (Formula presented.) is only 6- to 26-fold than OH toward substrates 2a-2h, although the former is over 11 pKa units less basic than the latter. Solvation and polarizability effects have been suggested to be responsible for the unusual reactivity shown by (Formula presented.) and OH. Effects of changing nucleophile from OH to (Formula presented) on reaction mechanism and reactivity are discussed in detail.