99-34-3

Usage

Chemical Properties

White to pale yellow monoclinic prismatic crystal. Soluble in alcohol and glacial acetic acid, slightly soluble in water, ether and carbon disulfide. Can be volatile with water vapor.

Uses

Different sources of media describe the Uses of 99-34-3 differently. You can refer to the following data:
1. 3,5-nitrobenzoic acid is an important intermediate for organic synthesis, in the pharmaceutical industry for the synthesis sulfachrysoidine and for the detection of ampicillin.
2. 3,5-Dinitrobenzoic acid, is used as a reagent used in the derivatization of resins and the determination of ampicillin.

Preparation

3,5-Dinitrobenzoic acid is synthesized by nitration of benzoic acid. Sulfuric acid was added to the dry reaction pot, and benzoic acid was added under stirring. Heat to 60°C, add fuming nitric acid dropwise, and complete the dropwise addition below 85°C. React at 80-85°C for 1 h, 100°C for 0.5-1h, and then heat up to 135°C for 2h. Leave overnight. The reaction solution was put into ice water to separate out crystals, filtered, washed with water and then washed with 50% ethanol to obtain 3,5-dinitrobenzoic acid. Yield 70%.

Application

3,5-Dinitrobenzoic Acid is used in fluorometric analysis of creatinine (which is a determinant of kidney function). Also used as a reagent in the synthesis of several organic compounds including that of rhodanine derivatives that act as aldose reductase inhibitors.

Definition

ChEBI: 3,5-dinitrobenzoic acid is a member of the class of benzoic acids that is benzoic acid in which the hydrogens at positions 3 and 5 are replaced by nitro groups. It is a C-nitro compound and a member of benzoic acids.

General Description

3,5-Dinitrobenzoic acid forms an adduct with 3,5-dimethylpyridine and the crystal structure of adduct has been studied at room temperature and 80K for both undeuterated and deuterated compounds. It forms 1:1 cocrystal with analgesic drug, ethenzamide and exists in two polymorphic forms.

Purification Methods

Crystallise the acid from distilled H2O or 50% EtOH (4mL/g). Dry it in a vacuum desiccator or at 70o over BaO under a vacuum for 6hours. [Beilstein 9 II 279, 9 III 1779, 9 IV 1242.]

InChI:InChI=1/C7H4N2O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)/p-1

Upstream product

• 606-37-1 2,4-dinitronaphthalene 
• 60411-31-6 1,2,6,8-tetranitronaphthalene 
• 860603-10-7 1-ethyl-3,5-dinitro-benzene 
• 42444-51-9 3,5-dinitrobenzoyl azide 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 98-07-7 Benzotrichlorid 
• 605-71-0 1,5-dinitronaphthalene 
• 67-64-1 acetone 
• 65-85-0 benzoic acid 
• 121-92-6 3-nitrobenzoic acid 
• 67-56-1 methanol 
• 2702-58-1 methyl 3,5-dinitrobenzoate 
• 64666-40-6 2-cyclopenten-1-yl 3,5-dinitrobenzoate 

Downstream Products

• 87112-33-2 3,5-dinitro-benzoic acid tetrahydropyran-2-yl ester 
• 2702-58-1 methyl 3,5-dinitrobenzoate 
• 107524-10-7 3,5-dinitro-benzoic acid-(1-methyl-1-phenyl-prop-2-ynyl ester) 
• 4110-35-4 3,5-dinitrobenzonitrile 
• 19402-64-3 ammonium benzenesulfonate 
• 98-11-3 benzenesulfonic acid 
• 1523-21-3 4-nitrophenyl 3,5-dinitrobenzoate 
• 110247-77-3 2,4-bis-(3,5-dinitro-benzoyloxy)-2,4-dimethyl-pentane 
• 618-71-3 ethyl 3,5-dinitrobenzoate 
• 5400-86-2 ethyl 3,5-dinitro-4-methylbenzoate 
• 59986-41-3 3,5-dinitro-benzoic acid-(2-ethyl-hexyl ester) 
• 107415-66-7 3,5-dinitro-benzoic acid-(1,1,2-trimethyl-propyl ester) 
• 103501-43-5 3,5-dinitro-benzoic acid-(1-methoxy-vinyl ester) 
• 99-33-2 3,5-dinitrobenoyl chloride 

Relevant academic research and scientific papers

Preparation method of 3,5-dinitrobenzoic acid

The invention discloses a preparation method of 3,5-dinitrobenzoic acid. The preparation method comprises the following steps: putting m-dinitrobenzene, a DMF solvent and a metal modified mesoporous material supported guanidine salt ionic liquid into a stainless steel high-pressure reaction kettle, introducing carbon dioxide, increasing the pressure of the carbon dioxide at 80-130 DEG C, keeping the pressure at a specified pressure, carrying out stirring and reacting for 4-20 hours to obtain 3,5-dinitrobenzoic acid, performing filtering to separate an organic phase and a catalyst phase of a product, subjecting a filtrate to distillation, and recrystallizing a crude product with ethanol to obtain a target product. According to the invention, a metal modified mesoporous material supported guanidine salt ionic liquid has good catalytic activity in a carboxylation reaction, a reaction process is high in atom economy, the process of reaction is green, no waste acid is generated, a catalyst can be conveniently recycled, and the preparation method is a novel green and environment-friendly preparation method.

As neuroprotective agents of pharmaceutical compounds

The invention discloses a medicinal compound as a neuroprotective agent. The medicinal compound is a neuronal nitric oxide synthase-postsynaptic density protein 95 (nNOS-PSD95) decoupling agent. The medicinal compound is a benzene ring derivative shown in the general formula (I) or its pharmaceutically acceptable salt. The invention further discloses a preparation method of the medicinal compound and a use of the medicinal compound in prevention and treatment on neuronal damage influence-caused diseases.

Electrofugalities of 1,3-diarylallyl cations

Heterolysis rate constants k1 of differently substituted 1,3-diarylallyl halides and carboxylates have been determined in various solvents. The linear free energy relationship log k1 = s f(Nf + Ef) was found to predict the heterolysis rates (log k1) of 1,3-diarylallyl derivatives with a standard deviation of 0.26, corresponding to a factor of 1.82 in k1, and maximum deviation in k1 of a factor of 5. Some systematic deviations are evident, however. Thus, 1,3-diarylallyl carboxylates always react faster and 1,3-diarylallyl chlorides always react more slowly than calculated by the quoted correlation equation when both types of leaving groups were used to determine the electrofugality parameters Ef. As 1,3-diarylalyl cations are generated faster in solvolysis reactions and also react faster with nucleophiles than benzhydrylium ions of similar thermodynamic stabilities, i.e., Lewis acidities, one can conclude that the reactions involving 1,3-diarylallyl cations proceed with lower intrinsic barriers than those involving benzhydrylium ions. The electrofugality parameters Ef of 1,3-diarylallylium ions determined in this work were combined with the electrophilicity parameters E of the corresponding cations as well as with the results on ion pair dynamics reported in preceding papers for generating the full mechanistic spectrum of 1,3-diarylallyl solvolyses.

Kinetic and safety characterization of the nitration process of methyl benzoate in mixed acid

The nitration of methyl benzoate is studied from a chemical and a kinetic point of view. The reaction network through which the system could evolve following the loss of thermal control or the uncorrect feed of the reagents is completely characterized. The data collected during the present investigation indicate that runaway phenomena can occur during the nitration of the substrate due to the development of side reactions. Isothermal experiments are thus carried out to estimate the unknown kinetic parameters through the adoption of a mathematical model able to predict the system behaviour upon variation of process parameters. The dependence of the acidity function H on the operating conditions is assessed. The proposed model and the estimated parameters are validated through the use of the results collected in a set of experimental runs performed at significantly different operating conditions from those adopted to identify them.

Method for estimating SN1 rate constants: Solvolytic reactivity of benzoates

Nucleofugalities of pentafluorobenzoate (PFB) and 2,4,6-trifluorobenzoate (TFB) leaving groups have been derived from the solvolysis rate constants of X,Y-substituted benzhydryl PFBs and TFBs measured in a series of aqueous solvents, by applying the LFER equation: log k = sf(Ef + Nf). The heterolysis rate constants of dianisylmethyl PFB and TFB, and those determined for 10 more dianisylmethyl benzoates in aqueous ethanol, constitute a set of reference benzoates whose experimental ΔG ? have been correlated with the ΔH? (calculated by PCM quantum-chemical method) of the model epoxy ring formation. Because of the excellent correlation (r = 0.997), the method for calculating the nucleofugalities of substituted benzoate LGs have been established, ultimately providing a method for determination of the SN1 reactivity for any benzoate in a given solvent. Using the ΔG? vs ΔH? correlation, and taking sf based on similarity, the nucleofugality parameters for about 70 benzoates have been determined in 90%, 80%, and 70% aqueous ethanol. The calculated intrinsic barriers for substituted benzoate leaving groups show that substrates producing more stabilized LGs proceed over lower intrinsic barriers. Substituents on the phenyl ring affect the solvolysis rate of benzhydryl benzoates by both field and inductive effects.

PROCESS FOR PREPARING SUBSTITUTED AROMATIC CARBOXYLIC ACIDS

A process for preparing an aromatic carboxylic acid having a heteroatom containing substituent is provided that includes reaction in a vessel of an aromatic precursor having an aromatic core with at least one heteroatom containing substituent and at least one hydrogen extending from the core, with a haloacetonitrile under reaction conditions to form an aromatic acetonitrile with an acetonitrile moiety. The aromatic acetonitrile is exposed to an oxidizing agent under conditions to convert the acetonitrile moiety to a carboxylic acid group to prepare the aromatic carboxylic acid having the heteroatom containing substituent.

Lithium chloride-assisted selective hydrolysis of methyl esters under microwave irradiation

A rapid and mild method for the selective hydrolysis of methyl ester in lithium chloride-N,N-dimethylformamide (LiCl-DMF) system under microwave irradiation has been developed. The effects of substituent, metal salt, and solvent on the reactivity and selectivity of the hydrolysis reaction have been investigated. Microwave irradiation significantly improves the reaction yield within a short time in an LiCl-DMF system. Moreover, the chiral-carbon of methyl esters retained its configuration during the reaction. Finally, the catalytic mechanism of hydrolysis by LiCl salt has also been proposed.

Effect of the leaving group solvation on solvolytic behavior of benzhydryl derivatives

An effect of the leaving group (LG) solvation on reactivity of benzhydryl derivatives in SN1 reactions has been investigated by using X, Y-substituted benzhydryl phenyl carbonates, methyl carbonates, 3, 5-dinitrobenzoates (DNB), and the corresponding benzhydryl chlorides as reference compounds. Reaction constants (sf) derived from LFER equation log k (25°C)=sf (Nf+Ef) indicate that s f parameters of carbonates and DNBs decrease as the fraction of the water in a given solvent/water mixture increases, while those of chlorides remain unchanged. This phenomenon is due to less important solvation and less charge separation in the TS. Effects of the solvents on the reaction rates were analyzed by Grunwald-Winstein correlations using various solvent-ionizing power scales. The m values obtained for carbonates and DNBs are considerably smaller than the m values for chlorides. Also, the solvolysis rate constants of substrates that have stronger electrofuges are less influenced by solvent (lower m) than those with weaker electrofuges. Values of m parameters obtained for a given substrate in a given binary solvent system correlate well with the electrofugality of the generated benzhydrylium ion. Abscissa at which m=0 represents the extrapolated critical electrofugality Ecrit f of the substrates whose solvolysis rates should not depend on the water fraction in the aqueous/organic solvent mixtures. Similar values for the critical electrofugality have also been obtained from extrapolated logk versus Ef plots. Copyright

Bromination of deactivated aromatics: A simple and efficient method

(Chemical Equation Presented) Highly deactivated aromatic compounds were smoothly monobrominated by treatment with N-bromosuccinimide (NBS) in concentrated H2SO4 medium affording the corresponding bromo derivatives in good yields. Mild reaction conditions and simple workup provides a practical and commercially viable route for the synthesis of bromo compounds of deactivated aromatics.