25412-75-3

Basic information

• Product Name: 4-nitrobenzamidine
• Synonyms: 4-nitrobenzamidine;4-Nitrobenzenecarbimide amide;4-Nitrobenzimidamide;Benzenecarboximidamide,4-nitro-;4-nitrobenzenecarboximidamide
• CAS NO: 25412-75-3
• Molecular Formula: C₇H₇N₃O₂
• Molecular Weight: 165.14938
• EINECS: 246-952-2
• Mol File: 25412-75-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 310.6°C at 760 mmHg
• Flash Point: 141.6°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.000596mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: 4-nitrobenzamidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrobenzamidine(25412-75-3)
• EPA Substance Registry System: 4-nitrobenzamidine(25412-75-3)

Safety Data

• Hazardous Substances Data: 25412-75-3(Hazardous Substances Data)

Usage

General Description

4-nitrobenzamidine is a chemical compound with the molecular formula C7H7N3O2. It is a yellow crystalline solid that is primarily used as a building block in the synthesis of pharmaceuticals and dyes. It is also used as a reagent in organic chemistry reactions, particularly in the synthesis of heterocyclic compounds. 4-nitrobenzamidine has been researched for its potential as an anti-cancer agent due to its ability to inhibit the growth of certain cancer cells. However, it is important to note that 4-nitrobenzamidine is a potentially hazardous chemical and should be handled with appropriate safety precautions and procedures.

InChI:InChI=1/C7H7N3O2/c8-7(9)5-1-3-6(4-2-5)10(11)12/h1-4H,(H3,8,9)

Upstream product

• 57-13-6 urea 
• 619-72-7 4-nitrobenzonitrile 
• 555-16-8 4-nitrobenzaldehdye 
• 52708-02-8 4-nitrobenzimidic acid methyl ester 
• 831-68-5 4-nitro-benzimidic acid ethyl ester 
• 192332-48-2 N'-hydroxy-4-nitrobenzimidamide 
• 39739-52-1 methyl imini ester hydrochloride of 4-nitrobenzoic acid 
• 3858-83-1 p-aminobenzamidine 
• 62-23-7 4-nitro-benzoic acid 
• 902-47-6 p-nitrobenzoic anhydride 
• 7647-01-0 hydrogenchloride 
• 930-69-8 sodium thiophenolate 
• 39184-67-3 3-chloro-3-(p-nitrophenyl)diazirine 
• 115127-49-6 3-bromo-3-(4-nitrophenyl)diazirine 

Downstream Products

• 92577-32-7 5,6-dimethyl-2-(4-nitro-phenyl)-3H-pyrimidin-4-one 
• 91397-16-9 4,6-dimethyl-2-(4-nitrophenyl)pyrimidine 
• 3858-83-1 p-aminobenzamidine 
• 1193709-63-5 N-{4,4a,5,6,7,8-hexahydro-5,6,7-trihydroxy-1-(4-nitrophenyl)-3-oxo-3H-pyrido[1,2-c]pyrimidin-4-yl}benzamide 
• 1193709-80-6 N-{4,4a,5,6,7,8-hexahydro-5,6,7-trihydroxy-8-(hydroxymethyl)-1-(4-nitrophenyl)-3-oxo-3H-pyrido[1,2-c]pyrimidin-4-yl}benzamide 
• 124595-98-8 5-chloro-2-(4-nitrophenyl)pyrimidine 
• 2498-50-2 4-aminobenzamidine dihydrochloride 
• 55978-27-3 N-(4-Nitrostyrylsulfonyl)-4-nitro-benzamidin 
• 51769-82-5 N-acetyl-4-nitrobenzamide 

Relevant articles and documents

A to prepare to aminobenzoic amidine hydrochloride method

The invention relates to the technical field of pharmaceutical chemistry and provides a method for preparing p-amino-benzamidine hydrochloride. The method comprises the following steps: (1) p-nitrobenzonitfile II undergoes an amidining reaction in an amidining reagent I to obtain an intermediate p-nitrobenzene methylenimine III; (2) the intermediate p-nitrobenzene methylenimine III undergoes an amidining reaction in an amidining reagent II to obtain p-nitrobenzamidine IV; and (3) under an acidic condition, p-nitrobenzamidine IV undergoes a reduction reaction in a reaction solvent II by the use of a reducing agent to obtain p-amino-benzamidine hydrochloride. In the step (1), the amidining reagent I is thionyl chloride, phosphorus trichloride or phosphorus pentachloride; in the step (2), the amidining reagent II is ammonium carbonate, ammonium bicarbonate or ammonium chloride; and in the step (3), the reaction solvent II is a mixed solvent of water and alcohols. The synthetic method provided by the invention is safe and simple and has advantages of high yield and good product quality. The preparation method of p-amino-benzamidine hydrochloride is suitable for industrial production.

Electrochemical and mARC-catalyzed enzymatic reduction of para-substituted benzamidoximes: Consequences for the prodrug concept "amidoximes instead of amidines"

The mitochondrial amidoxime reducing component (mARC) activates amidoxime prodrugs by reduction to the corresponding amidine drugs. This study analyzes relationships between the chemical structure of the prodrug and its metabolic activation and compares its enzyme-mediated vs. electrochemical reduction. The enzyme kinetic parameters KM and Vmax for the N-reduction of ten para-substituted derivatives of the model compound benzamidoxime were determined by incubation with recombinant proteins and subcellular fractions from pig liver followed by quantification of the metabolites by HPLC. A clear influence of the substituents at position 4 on the chemical properties of the amidoxime function was confirmed by correlation analyses of 1H NMR chemical shifts and the redox potentials of the 4-substituted benzamidoximes with Hammett's σ. However, no clear relationship between the kinetic parameters for the enzymatic reduction and Hammett's σ or the lipophilicity could be found. It is thus concluded that these properties as well as the redox potential of the amidoxime can be largely ignored during the development of new amidoxime prodrugs, at least regarding prodrug activation.

Structural and biochemical basis for the firm chemo- and regioselectivity of the nitro-forming N-oxygenase AurF

Site-directed mutagenesis based on the crystal structure of AurF, a nitro group forming monooxygenase from Streptomyces thioluteus, revealed that AurF variants are capable of selectively transforming guanidyl- and amidinyl-substituted anilines into the corresponding nitro compounds. Our results provide new insights into the biochemical basis of regioselective N-oxygenation. The Royal Society of Chemistry.