2900-63-2

Basic information

• Product Name: 3,5-Dinitrobenzohydrazide
• Synonyms: 3,5-DINITRO-BENZOIC ACID HYDRAZIDE;3,5-DINITROBENZHYDRAZIDE;3,5-dinitrobenzohydrazide;Einecs 220-790-2;Benzoic acid, 3,5-dinitro-, hydrazide
• CAS NO: 2900-63-2
• Molecular Formula: C₇H₆N₄O₅
• Molecular Weight: 226.15
• EINECS: 220-790-2
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 2900-63-2.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• Density: 1.608g/cm³
• Refractive Index: 1.659
• CAS DataBase Reference: 3,5-Dinitrobenzohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dinitrobenzohydrazide(2900-63-2)
• EPA Substance Registry System: 3,5-Dinitrobenzohydrazide(2900-63-2)

Safety Data

• Hazardous Substances Data: 2900-63-2(Hazardous Substances Data)

Usage

General Description

3,5-Dinitrobenzohydrazide is a chemical compound with the molecular formula C7H4N4O4. It is a yellow crystalline powder that is primarily used as a reagent for the detection and determination of ketones and aldehydes. 3,5-Dinitrobenzohydrazide forms a stable complex with the carbonyl group of ketones and aldehydes, leading to the formation of an orange-red precipitate. This reaction is often used in qualitative and quantitative analysis of these organic compounds in various chemical and environmental samples. Additionally, this compound has also been explored for potential applications in the synthesis of pharmaceuticals and other organic compounds. However, it is important to handle this chemical with caution due to its potential hazardous and toxic properties.

InChI:InChI=1/C7H6N4O5/c8-9-7(12)4-1-5(10(13)14)3-6(2-4)11(15)16/h1-3H,8H2,(H,9,12)

Upstream product

• 618-71-3 ethyl 3,5-dinitrobenzoate 
• 2702-58-1 methyl 3,5-dinitrobenzoate 
• 1523-21-3 4-nitrophenyl 3,5-dinitrobenzoate 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 99-34-3 3,5-dinitrobenzoic acid 
• 136367-45-8 2-chloro-4-nitrophenyl 3,5-dinitrobenzoate 

Downstream Products

• 91330-77-7 furfural-(3,5-dinitro-benzoylhydrazone) 
• 98284-70-9 3,5-dinitro-benzoic acid decylidenehydrazide 
• 93003-99-7 D-xylose-(3,5-dinitro-benzoylhydrazone) 
• 42444-51-9 3,5-dinitrobenzoyl azide 
• 349640-90-0 N,N'-bis-(3,5-dinitro-benzoyl)-hydrazine 
• 124525-20-8 3-(3,5-dinitro-benzoylhydrazono)-butyric acid ethyl ester 
• 39575-23-0 3,5-dinitro-benzoic acid benzylidenehydrazide 
• 2900-65-4 3,5-dinitro-benzoic acid ethylidenehydrazide 

Relevant articles and documents

Aromatic acyl hydrazone derivative and application thereof as NA inhibitor

The invention relates to an aromatic acyl hydrazone derivative as shown in a structural formula I, pharmaceutically acceptable salt and a pharmaceutical composition thereof, and application of the aromatic acyl hydrazone derivative and the pharmaceutically acceptable salt and the pharmaceutical composition in preparation of an influenza virus neuraminidase inhibitor, wherein R is one of trifluoromethyl, nitryl, 3-methyl-4-nitryl, 3-hydroxyl-4-nitryl, 3-nitryl-4-hydroxyl, hydroxyl, dihydroxyl, dinitryl, 3-methoxy-4-hydroxyl or trihydroxyl; Y is selected from hydroxyl, dihydroxyl, 2-hydroxyl-3-methoxy, 2-hydroxyl-4-methoxy,2-hydroxyl-5-methoxy,2-hydroxyl-6-methoxy,3-hydroxyl-2-methoxy,3-hydroxyl-4-methoxy,3-hydroxyl-5-methoxy,3-hydroxyl-6-methoxy,4-hydroxyl-2-methoxy,4-hydroxyl-3-methoxy,4-hydroxyl-3,5-dimethoxy, trihydroxyl, 4-hydroxyl-3-ethoxy, or 4-hydroxyl-3,5-dimethoxy; w is selected from CH or N; and z is selected from CH or N.

Structural design, synthesis and substituent effect of hydrazone-N-acylhydrazones reveal potent immunomodulatory agents

4-(Nitrophenyl)hydrazone derivatives of N-acylhydrazone were synthesized and screened for suppress lymphocyte proliferation and nitrite inhibition in macrophages. Compared to an unsubstituted N-acylhydrazone, active compounds were identified within initial series when hydroxyl, chloride and nitro substituents were employed. Structure-activity relationship was further developed by varying the position of these substituents as well as attaching structurally-related substituents. Changing substituent position revealed a more promising compound series of anti-inflammatory agents. In contrast, an N-methyl group appended to the 4-(nitrophenyl)hydrazone moiety reduced activity. Anti-inflammatory activity of compounds is achieved by modulating IL-1β secretion and prostaglandin E2 synthesis in macrophages and by inhibiting calcineurin phosphatase activity in lymphocytes. Compound SintMed65 was advanced into an acute model of peritonitis in mice, where it inhibited the neutrophil infiltration after being orally administered. In summary, we demonstrated in great details the structural requirements and the underlying mechanism for anti-inflammatory activity of a new family of hydrazone-N-acylhydrazone, which may represent a valuable medicinal chemistry direction for the anti-inflammatory drug development in general.

Design and optimization of N-acylhydrazone pyrimidine derivatives as E. coli PDHc E1 inhibitors: Structure-activity relationship analysis, biological evaluation and molecular docking study

By targeting the thiamin diphosphate (ThDP) binding site of Escherichia coli (E. coli) pyruvate dehydrogenase multienzyme complex E1 (PDHc E1), a series of novel ‘open-chain’ classes of ThDP analogs A, B, and C with N-acylhydrazone moieties was designed and synthesized to explore their activities against E. coli PHDc E1 in vitro and their inhibitory activity against microbial diseases were further evaluated in vivo. As a result, A1–23 exhibited moderate to potent inhibitory activities against E. coli PDHc E1 (IC50 = 0.15–23.55 μM). The potent inhibitors A13, A14, A15, C2, had strong inhibitory activities with IC50 values of 0.60, 0.15, 0.39 and 0.34 μM against E. coli PDHc E1 and with good enzyme-selective inhibition between microorganisms and mammals. Especially, the most powerful inhibitor A14 could 99.37% control Xanthimonas oryzae pv. Oryzae. Furthermore, the binding features of compound A14 within E. coli PDHc E1 were investigated to provide useful insights for the further construction of new inhibitor by molecular docking, site-directed mutagenesis, and enzymatic assays. The results indicated that A14 had most powerful inhibition against E. coli PDHc E1 due to the establishment of stronger interaction with Glu571, Met194, Glu522, Leu264 and Phe602 at active site of E.coli PDHc E1. It could be used as a lead compound for further optimization, and may have potential as a new microbicide.