14552-00-2

Usage

Chemical structure

A nitroaromatic compound containing a pyrrolizine ring and two nitro groups

Toxicity

Highly toxic

Use

Research and as a sensitizing agent in the study of allergic contact dermatitis

Reactivity

Highly reactive

Effects on humans

Can cause severe skin irritation and allergic reactions

Classification

Potential carcinogen and mutagen

Regulation

Highly regulated and controlled in many countries

Restrictions

Use mainly restricted to research and industrial applications

Safety measures

Proper safety measures should be taken when handling and disposing of 1-Pyrrolizino-2,4-dinitrobenzene.

InChI:InChI=1/C10H11N3O4/c14-12(15)8-3-4-9(10(7-8)13(16)17)11-5-1-2-6-11/h3-4,7H,1-2,5-6H2

Upstream product

• 123-75-1 pyrrolidine 
• 2486-07-9 2,4-dinitrophenyl phenyl ether 
• 13181-75-4 O-(2,4-dinitrophenyl) cyclohexanone oxime 
• 75735-29-4 (E)-O-(2,4-dinitrophenyl)benzaldoxime 
• 75735-26-1 O-(2,4-dinitrophenyl)-p-nitrobenzaldoxime 
• 13181-14-1 1-phenylethan-1-one O-(2,4-dinitrophenyl) oxime 
• 17188-67-9 diphenylmethanone O-(2,4-dinitrophenyl)oxime 
• 115806-86-5 O-(2,4-dinitrophenyl)-4'-bromobenzophenone oxime 
• 25150-61-2 pyrrolidine hydrochloride 
• 17188-66-8 O-(2,4-dinitrophenyl)-p,p'-dichlorobenzophenone oxime 
• 173416-64-3 O-(2,4-dinitrophenyl)-p,p'-difluorobenzophenone oxime 
• 173416-65-4 O-(2,4-dinitrophenyl)-p,p'-dimethoxybenzophenone oxime 
• 13181-22-1 O-(2',4'-dinitrophenyl) 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one oxime 
• 70-34-8 2,4-Dinitrofluorobenzene 

Downstream Products

• 2044-88-4 N-methyl-2,4-dinitroaniline 
• 51-28-5 2,4-Dinitrophenol 
• 5367-55-5 5-nitro-2-pyrrolidin-1-yl-aniline 

Relevant academic research and scientific papers

Photoredox catalyzed dealkylative aromatic halogen substitution with tertiary amines

A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are

Synthesis of o-Nitroarylamines via Ipso Nucleophilic Substitution of Sulfonic Acids

A mild, efficient, and eco-friendly method for the synthesis of o-nitroarylamine from o-nitroaryl sulfonic acid via ipso nucleophilic aryl substitution by amine is described. The products have been obtained with good yields at room temperature without the assistance of any metal, activating agent, or toxic oxidant. This method is useful for racemization-free synthesis of N-aryl amino acid esters.

Pd(OAc)2-catalyzed dinitration reaction of aromatic amines

Taking advantage of Pd(OAc)2-catalyzed dinitration reactions with Bi(NO3)3·5H2O in trifluoroethanol (TFE) and trifluoroacetic acid (TFA), we have developed an efficient and practical method for the synthesis of secondary dinitro-aromatic amines. The products could be applied to the preparation of 5-amine-N-methyl-benzimidazolone, the azo-dyes, economic advantages. The method has also been expanded to the dinitration reaction of some tertiary aromatic amines.

ONSH: Optimization of oxidative alkylamination reactions through study of the reaction mechanism

(Figure presented) Oxidative alkylamination of electron-deficient (hetero)aromatic compounds, via the nucleophilic substitution of hydrogen, is a methodology that has made significant progress since the introduction of AgPy2MnO4 as oxidant. This oxidant generally gives good conversions and yields, whereas the use of KMnO4 only sometimes works equally well. In order to rationalize this, the reaction mechanism of oxidative alkylamination has been studied. 3-Nitropyridine (1), 1,3-dinitrobenzene (2), and quinazoline (3) were chosen as model substrates and n-butylamine and pyrrolidine as model alkylamines. The rate-limiting step of the mechanism for these substrate/alkylamine combinations was determined. With the use of 1H NMR spectroscopy thermodynamic properties of σ-- adduct formation were deduced and the effect of additives on the adduct formation was investigated. The fundamental insights resulting from these studies led to the identification of a cheap additive (tetrabutylammonium chloride), which in combination with the standard and cheap oxidant KMnO 4 generally gave excellent yields, similar to the ones previously obtained with more expensive AgPy2MnO4.

Kinetics of snar reactions of 1-phenoxy-nitrobenzenes with aliphatic amines in toluene: Ring substituent and solvent effects on reaction pathways

Rate constants are reported for the reactions of a series of 4-substituted-1-phenoxy-2,6-dinitrobenzenes 1 and 6-substituted-1-phenoxy-2,4- dinitrobenzenes 2 activated by CF3, COOCH3, CN, NO 2 groups or by ring-nitrogen wi

The effects of ring substituents and leaving groups on the kinetics of SNAr reactions of 1-halogeno- and 1-phenoxy-nitrobenzenes with aliphatic amines in acetonitrile

Rate constants are reported for the reactions of a series of 1-chloro-, 1-fluoro- and 1-phenoxy-nitrobenzenes activated by CF3 or CN groups or by ring-nitrogen with n-butylamine, pyrrolidine or piperidine in acetonitrile. The results are compar

Kinetic studies on the reactions of O-(2′,4′-dinitrophenyl) 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime with nucleophiles in aprotic solvents - Mechanism for the uncatalysed pathway

Kinetics of the reactions of the title compound with some amines as nucleophiles in aprotic solvents have been investigated at the λmax of the aminolysis product at 35 ± 0.1 °C under pseudo-first order conditions. The reaction is overall second order, first with respect to each reactant. The second order rate coefficients decreased with increase in [amine] in all cases. Formation of an electron donor-acceptor complex is indicated. The temperature effect on the reaction rate has been studied in the range (293-318 K). The entropy of activation parameters are large and negative in all cases indicating formation of a crowded transition state. Mechanistic interpretation is given.

Effects of ortho- and para-ring activation on the kinetics of S NAr reactions of 1-chloro-2-nitro- and 1-phenoxy-2-nitrobenzenes with aliphatic amines in acetonitrile

Rate constants are reported for reaction of 4-substituted 1-chloro-2,6-dinitrobenzenes 1, 6-substituted 1-chloro-2,4-dinitrobenzenes 2, and some of the corresponding 1-phenoxy derivatives, 3 and 4, with n-butylamine, pyrrolidine and pi-peridine in acetoni

2H-benzimidazole 1,3-dioxide derivatives: A new family of water-soluble anti-trypanosomatid agents

Three series of benzimidazole N-oxide derivatives were developed and were examined for their activity against trypanosomatid parasites (Trypanosoma cruzi and Leishmania spp.). 2H-Benzimidazole 1,3-dioxides displayed remarkable in vitro activities against

Effect of nucleophile on the kinetics of the reactions of O-(2′,4′-dinitrophenyl)-4-phenyl-3-buten-2-one oxime in acetonitrile

The kinetics of the reactions of O-(2′,4′ -dinitrophenyl)-4-phenyl-3-buten-2-one oxime have been studied with piperidine, cyclohexylamine, n-butylamine and pyrrolidine in acetonitrile at 35 ± 0.1°. Base catalysis has been observed with piperidine and pyrrolidine. Mechanistic interpretation is given.