101-24-6

Basic information

• Product Name: 3-nitro-N-(3-nitrophenyl)benzamide
• Synonyms: 3-Nitro-N-(3-nitrophenyl)benzamide;3,3'-dinitrobenzanilide
• CAS NO: 101-24-6
• Molecular Formula: C₁₃H₉N₃O₅
• Molecular Weight: 287.22766
• EINECS: 202-927-8
• Mol File: 101-24-6.mol

Chemical Properties

• Boiling Point: 384.6°Cat760mmHg
• Flash Point: 186.4°C
• Appearance: /
• Density: 1.496g/cm³
• CAS DataBase Reference: 3-nitro-N-(3-nitrophenyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-nitro-N-(3-nitrophenyl)benzamide(101-24-6)
• EPA Substance Registry System: 3-nitro-N-(3-nitrophenyl)benzamide(101-24-6)

Safety Data

• Hazardous Substances Data: 101-24-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3,3'-Dinitrobenzanilide is used as a synthetic intermediate for the preparation of other organic compounds. Its structural versatility allows chemists to modify and functionalize the molecule, leading to the development of new compounds with specific properties and applications.
Used in Medicinal Chemistry:
3,3'-Dinitrobenzanilide is used as a lead compound in the discovery and development of new pharmaceutical agents. The presence of the nitro and amide groups can be exploited to design molecules with potential biological activities, such as antimicrobial, antiviral, or anticancer properties.
Used in Material Science:
3,3'-Dinitrobenzanilide can be used as a building block for the synthesis of novel materials with specific characteristics. 3,3'-dinitrobenzanilide's structural features can be utilized to create materials with unique optical, electronic, or mechanical properties, which can be applied in various industries, such as electronics, photonics, or nanotechnology.
Used in Analytical Chemistry:
3,3'-Dinitrobenzanilide can be employed as a reagent or a reference compound in analytical techniques, such as chromatography, spectroscopy, or electrochemistry. Its distinct chemical properties can be used to study the behavior of other compounds or to develop new analytical methods for the detection and quantification of specific substances.

Upstream product

• 99-09-2 3-nitro-aniline 
• 121-90-4 m-nitrobenzoic acid chloride 
• 13277-62-8 m-nitrobenzoyl bromide 

Downstream Products

• 101-12-2 3,3'-Diaminobenzanilide 

Relevant articles and documents

Naphthalene-1,8-diylbis(diphenylmethylium) as an organic two-electron oxidant: Benzidine synthesis via oxidative self-coupling of N,N-dialkylanilines

Naphthalene-1,8-diylbis(diphenylmethylium) exhibits a unique electron-transfer reduction behavior due to the close proximity of the two triarylmethyl cations, which form a C-C bond while accepting two electrons, leading to 1,1,2,2-tetraphenylacenaphthene. The preparation of the dication was readily accomplished under anhydrous conditions starting from a cyclic bis(triarylmethyl) ether, derived from 1,8-dibromonaphthalene. The process proceeded via deoxygenation accompanying the formation of a disiloxane on treatment with a silylating agent (Me3SiClO4 or Me 3SiOTf) in 1,1,1,3,3,3-hexafluoropropan-2-ol. The dication was successfully employed for oxidative coupling of N,N-dialkylanilines at the paraposition to afford the corresponding benzidines in good to excellent yield.

EFFECT OF THE STRUCTURE OF THE REAGENTS IN THE REACTIONS OF AROYL CHLORIDES WITH N-METHYLARYLAMINES, CATALYZED BY TETRABUTYLAMMONIUM CHLORIDE IN BENZENE

The reactions of aroyl chlorides with N-methylarylamines, catalyzed by tetrabutylammonium chloride, lead to the formation of a complex with a hydrogen bond between the arylamine and the catalyst and its subsequent slow reaction with the aroyl chloride.The influence of the inductive effects of the substituents on the rate constants for the reaction of the aroyl chlorides with the intermediate complex and on the catalytic rate constants is described by two-parameter correlation equations.The role "amide conjugation" in the investigated processes is discussed.

JOINT EFFECT OF STRUCTURE OF REAGENTS AND TEMPERATURE ON REACTIVITY OF AROYL BROMIDE-PRIMARY ARYLAMINE SYSTEMS IN BENZENE. CROSSED CORRELATION

The kinetics of the reactions of aroyl bromides with primary arylamines in benzene were studied at 10, 25, 40, and 55 deg C.The effects of factors (temperature, the structure of the aroyl bromides and primary arylamines) varied separately and in pairs and also the joint effect of the three factors on the process rate were assessed quantitatively.The joint effect of the structure of the primary arylamines and the temperature on the reactivity of the system is nonadditive, and the effect of the structure of the aroyl bromides and temperature is additive.The influence of the varied parameters on the nature of the translation states in the reactions is discussed.

EFFECT OF THE STRUCTURE ON THE RATE OF THE REACTIONS OF AROYL CHLORIDES WITH PRIMARY ARYLAMINES IN MIXTURES OF tert-BUTYL ALCOHOL AND CHLOROBENZENES. THE TRANSITION THROUGH ISOPARAMETRIC POINTS WITH RESPECT TO THE STRUCTURE PARAMETERS

The rate of the reactions of aroyl chlorides with primary arylamines in 3.5, 5, and 7M solutions of tert-butyl alcohol in chlorobenzene at 25 deg C was measured.The effect of the structure of the reagents on the process rate was determined quantitatively by means of the Hammett-Taft and crossed correlation equations.The isoparametric points with respect to the structure of the substrate and the nucleophile were reached experimentally, and the transition through some of these points was also realised.It was found that the specific solvation of the primary arylamines by the tert-butyl alcohol was nonuniform in that an incre ase in the concentration of the alcohol in the investigated range reduced, did not change, and increased the rates of the reactions with 3-chloroaniline, 3-nitroaniline, and 3-nitro-5-methoxycarbonylaniline respectively.The effect of specific solvation on the behavior of the correlation parameters is discussed.

TRANSITION THROUGH AN ISOPARAMETRIC POINT RELATIVE TO SUBSTITUENT IN THE REACTION OF AROYL BROMIDES WITH PRIMARY ARYLAMINES. RELATIONSHIP BETWEEN REACTIVITY AND SELECTIVITY

Rates were measured for the reactions of aroyl bromides with primary arylamines in 1:1 chlorobenzene-cyclohexane at 25 deg C.The kinetic data were treated by the Hammett-Taft equations and cross correlation.This is the first reported transition through an isoparametric point relative to the structure of the nucleophile accompanied by inversion of the sign of the sensitivity parameter relative to the substrate structure in the aroyl bromide-primary arylamine reaction system.The results of the cross correlation analysis were interpreted on the basis of a concerted mechanism involving nucleophilic substitution at the carbonyl carbon atom.The relationship between the reactivity of the system studied and its selectivity was examined.

MUTUAL EFFECT OF THE STRUCTURES OF THE REAGENTS ON THE RATE OF THE REACTIONS OF AROYL CHLORIDES WITH PRIMARY ARYLAMINES IN DIOXANE AND MIXTURES OF CHLOROBENZENE WITH tert-BUTYL ALCOHOL

The rate of the reactions of aroyl chlorides with primary arylamines in specifically solvating media (dioxane, 0.1 M and 2 M solutions of tert-butyl alcohol in chlorobenzene) was measured.The joint effect of the structures of the reagents on the rate of the process in the employed media assessed quantitatively by crossed correlation.It was shown that the mutual effect of the structural factors on the reactivity is nonadditive in a 0.1 M solution of tert-butyl alcohol in chlorobenzene and additive in dioxane and also in a 2 M solution of tert-butyl alcohol in chlorobenzene.The effect of the structure of the reagents and specific solvation on the nature of the transition states of the reactions is discussed.

JOINT EFFECT OF THE STRUCTURE OF THE REAGENTS AND THE POLARITY OF THE MEDIUM ON THE RATE OF REACTIONS OF AROYL CHLORIDES WITH PRIMARY ARYLAMINES. CROSSED CORRELATION

The kinetics of the reactions of aroyl chlorides with primary arylamines in volume mixtures of chlorobenzene with nitrobenzene were studied with crossed variation in the structures of the reagents.The effect of various factors (the structure of the primary arylamines, the structure of the aroyl chlorides, the polarity of the medium), varied separately and in pairs, and also the joint effect of the three factors on the process rate were assessed.It was found that the structure of the reagents and the polarity of the medium have a nonadditive type of mutual effect on the reactivity of the aroyl chloride-primary arylamine system.The influence of the varied factors on the nature of the transition states in the reactions is discussed.

JOINT STRUCTURAL EFFECTS IN THE REACTIONS OF AROYL CHLORIDES WITH PRIMARY ARYLAMINES, CATALYZED BY TETRABUTYLAMMONIUM CHLORIDE IN BENZENE

The reactions of aroyl chlorides with arylamines, catalyzed by tetrabutylammonium chloride, take place with the equilibrium formation of a hydrogen-bonded complex of the arylamine with the catalyst and its subsequent reaction with the aroyl chloride.The joint structural effects of the substituents in the molecules of the reagents on the bimolecular rate constants (k2) for the reactions of aroyl chlorides with the complexes and the catalytic rate constants (kB) are described by many-parameter correletion equations.

Anti-allergic oxanilate compounds

A method of treating mammals for allergy and anaphylactic reactions of a reagin or non-reagin mediated nature which comprises administering prophylactically to said mammal an anti-allergy or anaphylactic reaction effective amount of a compound of the formula STR1 Novel compounds and compositions are also claimed.