33240-96-9

Usage

Uses

Used in Dye and Pigment Manufacturing:
3-NITROANILINE HYDROCHLORIDE is used as a key intermediate in the production of various dyes and pigments due to its chemical properties that facilitate color development and stability.
Used in Pharmaceutical Industry:
3-NITROANILINE HYDROCHLORIDE is utilized as a building block in the synthesis of certain pharmaceuticals, contributing to the development of new drugs and medications.
Used in Chemical Research:
In the field of chemical research, 3-NITROANILINE HYDROCHLORIDE serves as a valuable compound for studying the properties and reactions of nitroaromatics, which can lead to advancements in organic chemistry and related disciplines.

InChI:InChI=1/C6H6N2O2.ClH/c7-5-2-1-3-6(4-5)8(9)10;/h1-4H,7H2;1H

Upstream product

• 64-17-5 ethanol 
• 15999-30-1 (3-nitro-phenyl)-carbonimidic acid dichloride 
• 618-46-2 m-Chlorobenzoyl chloride 
• 99-09-2 3-nitro-aniline 
• 121-90-4 m-nitrobenzoic acid chloride 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 102-38-5 N-(3-nitrophenyl)formamide 
• 99-65-0 meta-dinitrobenzene 
• 52038-84-3 3-chlorophenyl methyl phosphonochloridothioate 
• 27976-53-0 4-methoxyphenyl methyl phosphonochloridothioate 
• 14410-08-3 4-methylphenyl methyl phosphonochloridothioate 
• 1186024-70-3 4-cyanophenyl methyl phosphonochloridothioate 
• 67-56-1 methanol 
• 14276-97-2 1-chloro-4-(α-chloro-isopropyl)-benzene 

Downstream Products

• 709-72-8 3-nitrophenylthiourea 
• 82720-55-6 N-(3-nitrophenyl)phosphorodichloridate 
• 71319-72-7 N-(3-nitrophenyl)ethane-1,2-diamine 
• 142992-99-2 N-(3-nitro-phenyl)-guanidine nitrate 
• 64782-02-1 1,2-Dichlor-cyclopenten-(1)-trion-(3,4,5)-<3-nitro-phenylhydrazon)-(4)> 
• 132769-07-4 N-(3-nitrophenyl)-4-(6-methoxymethoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)butylamide 
• 58759-63-0 5-nitro-2-mercaptobenzothiazole 
• 39652-36-3 3-Nitrophenyliminobisdichlorphosphin 

Relevant academic research and scientific papers

Synthesis and evaluation of some benzothiazole derivatives as antidiabetic agents

Objective: The objective of the present research investigation involves synthesis and biological evaluation of antidiabetic activity of benzothiazole derivatives. Methods: A novel series of benzothiazole derivatives 7(a-l) were synthesised and synthesised compounds were characterised for different physical and chemical properties like molecular formula, molecular weight, melting point, percentage yield, Rf value, IR,1HNMR,13CNMR and mass spectroscopy. The newly synthesised benzothiazole derivatives were subsequently assayed in vivo to investigate their hypoglycemic activity by the alloxan-induced diabetic model in rats. Results: All the synthesised derivatives showed significant biological efficacy. The compound 7d at 350 mg/kg exerted maximum glucose lowering effects whereas 7c showed minimum glucose lowering effects. All the compounds were effective, and experimental results were statistically significant at p0.01 and p0.05 level. Conclusion: From the results, it is clear that compound 7d demonstrated potent anti-diabetic activity and would be of better use in drug development to combat the metabolic disorder in future.

The ortho effect on the acidic and alkaline hydrolysis of substituted formanilides

The kinetics of formanilides hydrolysis were determined under first-order conditions in hydrochloric acid (0.01-8 M, 20-60°C) and in hydroxide solutions (0.01-3 M, 25 and 40°C). Under acidic conditions, second-order specific acid catalytic constants were used to construct Hammett plots. The ortho effect was analyzed using the Fujita-Nishioka method. In alkaline solutions, hydrolysis displayed both first- and second-order dependence in the hydroxide concentration. The specific base catalytic constants were used to construct Hammett plots. Ortho effects were evaluated for the first-order dependence on the hydroxide concentration. Formanilide hydrolyzes in acidic solutions by specific acid catalysis, and the kinetic study results were consistent with the AAC2 mechanism. Ortho substitution led to a decrease in the rates of reaction due to steric inhibition of resonance, retardation due to steric bulk, and through space interactions. The primary hydrolytic pathway in alkaline solutions was consistent with a modified BAC2 mechanism. The Hammett plots for hydrolysis of meta- and para-substituted formanilides in 0.10 M sodium hydroxide solutions did not show substituent effects; however, ortho substitution led to a decrease in rate constants proportional to the steric bulk of the substituent.

A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-Narylacetamides catalyzed by SOCl2

Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides. Springer Science+Business Media B.V. 2011.

Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system

The system 1,1,3,3-tetramethyldisiloxane (TMDS)/Fe(acac)3 is reported here as a new method to obtain amines from aromatic nitro compounds. Amines are synthetized in a straightforward step and are isolated as hydrochloride salts with good to excellent yields. This system has shown a good selectivity toward aryl-chloride, aryl-bromide, ester, carboxylic acid, and cyano groups. The reduction of alkylnitro compounds was unfortunately not possible using this method, only a mixture of mono and dialkylated amine was obtained.

Iron-catalyzed selective reduction of nitro compounds to amines

An efficient reduction of the nitro group with a catalytic amount of Fe(acac)3 and TMDS in THF at 60 °C affording the corresponding amine is described.

Highly chemo- and regioselective reduction of aromatic nitro compounds using the system silane/oxo-rhenium complexes

(Chemical Equation Presented) The reduction of aromatic nitro compounds to the corresponding amines with silanes catalyzed by high valent oxo-rhenium complexes is reported. The catalytic systems PhMe2SiH/ReIO 2(PPh3)2 (5 mol %) and PhMe2SiH/ ReOCl3(PPh3)2 (5 mol %) reduced efficiently a series of aromatic nitro compounds in the presence of a wide range of functional groups such as ester, halo, amide, sulfone, lactone, and benzyl. This methodology also allowed the regioselective reduction of dinitrobenzenes to the corresponding nitroanilines and the reduction of an aromatic nitro group in presence of an aliphatic nitro group. 2009 American Chemical Society.

Concurrent primary and secondary deuterium kinetic isotope effects in anilinolysis of O-aryl methyl phosphonochloridothioates

The nucleophilic substitution reactions of Y-O-aryl methyl phosphonochloridothioates with substituted anilines (XC6H 4NH2) and deuterated anilines (XC6H 4ND2) are investigated kinetically in acetonitrile at 55.0°C. The Hammett and Bronsted plots for substituent (X) variations in the nucleophiles are biphasic concave downwards with a break region between X = H and 4-Cl. The deuterium kinetic isotope effects (DKIEs) are primary normal (kH/kD = 1.03-1.30) for stronger nucleophiles (X = 4-MeO, 4-Me and H), and extremely large secondary inverse (kH/kD = 0.367-0.567) for weaker nucleophiles (X = 4-Cl, 3-Cl and 3-NO2). The cross-interaction constants are negative (ρXY(H) = -0.95 and ρXY(D) = -1.11) for stronger nucleophiles, while positive (ρXY(H) = +0.77 and ρXY(D) = +0.21) for weaker nucleophiles. These kinetic results indicate that the mechanism changes from a concerted process involving frontside nucleophilic attack for stronger nucleophiles to a stepwise process with a rate-limiting leaving group expulsion from the intermediate involving backside attack for weaker nucleophiles. A hydrogen-bonded, four-center-type transition state (TS) is suggested for a frontside attack, while a trigonal bipyramidal pentacoordinate TS is suggested for a backside attack. The unusually small DKIEs, as small as or equal to 0.4, for weaker nucleophiles seem to be ascribed to severe steric congestion in the TS.

NUCLEOPHILIC SUBSTITUTION REACTIONS OF CUMYL CHLORIDES IN METHANOL

Nucleophilic substitution reactions of cumyl chlorides with anilines in methanol have been investigated.Large negative ρY+ values in methanol and weak chloride common ion rate depression support a mechanism in which a preformed benzylic-type carbocation intermediate reacts with the solvent and the added nucleophile, aniline.All positive ρX (ρnuc) values observed and the estimated non-interactive point, ?Y+ = 0.72, strongly suggest that deprotonation of a mobile proton from the nucleophile occurs during the reaction.Fair linear correlation is exhibited for the plot of stability of carbocation, as expressed by the enthalpy of cation formation (AM1), and ?Y+, indicating that the thermodynamic driving force is nearly compensated for by the intrinsic barrier.

Joint effect of the structure and medium on the rate of reactions of aroyl chlorides with primary arylamines in mixtures of tert-butyl alcohol with chlorobenzene. Isoparametric points with respect to the variable parameters

The effects of the composition of the medium (3.5, 5, and 7 M solutions of tert-butyl alcohol in chlorobenzene), of pairs of variable factors (the composition of the medium with the structure of the aroyl chlorides and the composition of the medium with the structure of the primary arylamines), and of all three factors together on the rate of the reactions of aroyl chlorides with primary arylamines were determined quantitatively.It was found that the mutual effects of the structure and the medium on the reactivity of the system were nonadditive.It was shown experimentally that there are isoparametric points with respect to the medium, the structure of the substrate, and the structure of the nucleophile, and the transition was made through some of these points.

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.