20195-22-6

Basic information

• Product Name: 2,4-dinitrobenzoyl chloride
• Synonyms: 2,4-dinitrobenzoyl chloride;EINECS 243-578-1;2,4-Dinitrobenzoic acid chloride
• CAS NO: 20195-22-6
• Molecular Formula: C₇H₃ClN₂O₅
• Molecular Weight: 230.56212
• EINECS: 243-578-1
• Mol File: 20195-22-6.mol

Chemical Properties

• Boiling Point: 352.1°C at 760 mmHg
• Flash Point: 166.7°C
• Appearance: /
• Density: 1.652g/cm³
• Vapor Pressure: 3.93E-05mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: 2,4-dinitrobenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dinitrobenzoyl chloride(20195-22-6)
• EPA Substance Registry System: 2,4-dinitrobenzoyl chloride(20195-22-6)

Safety Data

• Hazardous Substances Data: 20195-22-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dinitrobenzoyl chloride is used as a reagent for the synthesis of new benzoyl hydrazones, which are compounds with potential applications in the development of pharmaceuticals. These benzoyl hydrazones exhibit antioxidant, anticholinesterase, and anticancer activities, making them valuable for the treatment of various diseases and conditions.
Used in Chemical Research:
In the field of chemical research, 2,4-Dinitrobenzoyl chloride serves as a key intermediate for the preparation of various organic compounds. Its unique structure allows for a wide range of chemical reactions, enabling the synthesis of new molecules with diverse properties and potential applications in various industries.
Used in Material Science:
2,4-Dinitrobenzoyl chloride can also be utilized in the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of novel materials with improved characteristics, such as enhanced stability, reactivity, or selectivity, which can be applied in various technological applications.

InChI:InChI=1/C7H3ClN2O5/c8-7(11)5-2-1-4(9(12)13)3-6(5)10(14)15/h1-3H

Upstream product

• 610-30-0 2,4-dinitrobenzoic acid 

Downstream Products

• 108272-92-0 phosphoric acid-(β,β'-bis-palmitoyloxy-isopropyl ester)-[2-(2,4-dinitro-benzoylamino)-ethyl ester] 
• 17586-89-9 2-(2,4-dinitro-phenyl)-benzothiazole 
• 50709-84-7 2,4-dinitrobenzophenone 
• 54948-58-2 2,4-dinitrobenzoyl azide 
• 106653-52-5 2,4-dinitro-benzoic acid-(4-chloro-3,5-dimethoxy-phenyl ester) 
• 99847-34-4 2,4-dinitro-benzoic acid-(4-hydroxy-anilide) 
• 374632-10-7 2,4-dinitro-benzoic acid p-toluidide 
• 24642-88-4 2,4-dinitro-benzoic acid p-anisidide 
• 108299-44-1 2,4-dinitro-benzoic acid-(4-dimethylamino-anilide) 
• 22978-56-9 2,4-dinitro-benzoic acid anilide 
• 525563-02-4 2,4-dinitro-benzoic acid m-toluidide 
• 99847-62-8 2,4-dinitro-benzoic acid-(3-hydroxy-anilide) 
• 58992-87-3 2,4-dinitro-benzoic acid-(2-diethylamino-ethyl ester) 
• 525563-19-3 2,4-dinitro-benzoic acid o-toluidide 

Relevant articles and documents

Synthesis, kinetics and biological assay of some novel aryl bis-thioureas: A potential drug candidates for Alzheimer's disease

A new series of bis-thioureas (4a-4j) was synthesized and characterized through spectroscopic and elemental analysis. The synthesized compounds 4a-4j were subjected to acetylcholinesterase enzyme (AChE) inhibition activity and free radical scavenging activity. The results of AChE inhibition assay were found to be active in inhibiting the target enzyme with different IC50 values. Among all derivatives, the 4 g showed highly potent inhibition potential against AChE enzyme with IC50 value of 0.1761±0.00768 μM, which is several times better than the reference inhibitor neostigmine methylsulfate IC50 2.469±0.069 μM. The initial structure-activity relationship (SAR) of 4 g revealed dual hydrogen bonding ability (donor and acceptor). Moreover, the electronic environment around the aromatic ring also greatly influenced the enzyme inhibition of AChE. To further explore the newly synthesized AChE inhibitors, kinetic studies were carried out to determine the mode of inhibition and it was found to be competitive inhibition. Pharmacokinetic predictions (ADMET parameters) were also evaluated and compounds showed good lead-like potential with little hepatotoxic and no skin-sensitive effects. The molecular docking studies delineated the binding affinity of the ligands with target protein and showed docking scores in the range of -10.3 to -7.6 kcal/mol.

Activation of carboxylic acids in asymmetric organocatalysis

Organocatalysis, catalysis using small organic molecules, has recently evolved into a general approach for asymmetric synthesis, complementing both metal catalysis and biocatalysis.1 Its success relies to a large extent upon the introduction of novel and generic activation modes.2 Remarkably though, while carboxylic acids have been used as catalyst directing groups in supramolecular transition-metal catalysis,3 a general and well-defined activation mode for this useful and abundant substance class is still lacking. Herein we propose the heterodimeric association of carboxylic acids with chiral phosphoric acid catalysts as a new activation principle for organocatalysis. This self-assembly increases both the acidity of the phosphoric acid catalyst and the reactivity of the carboxylic acid. To illustrate this principle, we apply our concept in a general and highly enantioselective catalytic aziridine-opening reaction with carboxylic acids as nucleophiles. Activation by dimerization: There is still no general activation mode for carboxylic acids in organocatalysis. The formation of heterodimers between chiral phosphoric acid diesters and carboxylic acids can be used to activate and direct reactivity of the latter in asymmetric reactions. This novel principle has been applied to the ring-opening desymmetrization and kinetic resolution of aziridines leading to valuable amino alcohols.

Synthesis, antimicrobial evaluation, and QSAR analysis of 2-isopropyl-5-methylcyclohexanol derivatives

A series of 2-isopropyl-5-methylcyclohexanol derivatives were synthesized and evaluated for their antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis and Gram-negative Escherichia coli and in vitro antifungal activity against Candida albicans and Aspergillus niger. The results of antimicrobial activity demonstrated that the compounds 10, 20, and 21 were the most active ones among the synthesized compounds. The QSAR studies revealed the importance of dipole moment (μ), total energy (Te), and topological parameters (κ1 and κ3) in describing the antimicrobial activity of 2-isopropyl-5-methylcyclohexanol derivatives. Springer Science+Business Media, LLC 2011.

Discovery of potent and stable conformationally constrained analogues of the MCH R1 antagonist SB-568849

A strategy of systematically targeting more rigid analogues of the known MCH R1 receptor antagonist, SB-568849, serendipitously uncovered a binding mode accessible to N-aryl-phthalimide ligands. Optimisation to improve the stability of this compound class led to the discovery of novel N-aryl-quinazolinones, benzotriazinones and thienopyrimidinones as selective ligands with good affinity for human melanin-concentrating hormone receptor 1.

Determining the σ-donor ability of the cyclopropane C-C bond

The low temperature crystal structures of ester and ether derivatives of varying electron demand, derived from cyclopropylmethanol 8 and dicyclopropylmethanol 9, have been determined. These structures show a very strong response of the C-OR bond distance to the electron demand of the OR substituent, demonstrating the strong σ-donor ability of the strained C-C bonds in the cyclopropane ring. The Royal Society of Chemistry 2005.

Low-temperature x-ray structural studies of the ester and ether derivatives of cis- and trans-4-tert-butyl cyclohexanol and 2-adamantanol: Application of the variable oxygen probe to determine the relative σ-donor ability of C-H and C-C bonds

Results of low-temperature X-ray structural studies for five cis-, and three trans-4-tert-butyl cyclohexanol, and six 2-adamantanol ester and ether derivatives are reported. Plots of C-OR bond distance against pKa(ROH) for derivatives of axial alcohol (5), equatorial alcohol (6) and 2-adamantanol derivatives (7) give slopes of -2.77 × 10-3, -2.86 × 10-3 and -3.05 × 10-3, respectively. Given that the relative differences in the slopes are modest, no clear distinction can be made about the relative σ-donor ability of a C-H bond and a C-C bond.

Nitro derivatives of cyclic sulfoximides of the 1,2-benzoisothiazole series

Nitro derivatives of 1-R-1,2-benzoisothiazol-3-one 1-oxide were synthesized by the reactions of 2-alkyl(phenyl)thio-4-nitro- and 4,6-dinitro-2-(phenylthio)benzamides with chlorine in 60% acetic acid. Analogous reactions of 2-(n-butylthio)-4-nitro- and 2-(tert-butylthio)-4-nitrobenzamides with chlorine afforded 2-butyl- and 2-H-1,2-benzoisothiazol-3-one 1-oxides, respectively. The proposed reaction mechanism includes the formation and subsequent transformations of S-alkyl-S-aryl- and S,S-diarylchlorosulfonium chlorides.

Synthesis of 2,3-dihydrobenzothiazol-1,1-dioxide and 2,3-dihydro-1,4-benzothiazin-3-one nitroderivatives from 2,4-di- and 2,4,6-trinitrobenzamides

Synthetic methods for the conversion of readily available 2,4-di- and 2,4,6-trinitrobenzamides to the previously unknown 2,3-dihydrobenzothiazol-1,1-dioxide, 2,3-dihydro- 1,4-benzothiazin-3-one, and 2,3-dihydro-1,4-benzothiazin-3-one-1,1-dioxide nitroderivatives have been developed. The methods involve selective nucleophilic substitution of an ortho-nitrogroup in polynitrobenzamides by benzylthio or methoxycarbonylmethylthio group followed by oxidation of sulfur atom with hydrogen peroxide and transformation of the amido group to the methoxycarbonylamino group by reaction with diacetoxyiodobenzene in methanol under non-basic conditions. Cyclization of the resulting compounds under the action of diacetoxyiodobenzene or sodium methoxide leads to the 2,3-dihydrobenzothiazole and 2,3-dihydro-1,4-benzothiazin-3one derivatives, respectively.

Selective synthesis of 1,2-benzisothiazol-3-one-1-oxide nitro derivatives

A new selective synthesis of 1,2-benzisothiazol-3-one-1-oxide nitro derivatives by reaction of 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in wet CH2Cl2 has been developed Reactions of N-unsubstituted 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in 60% AcOH give, instead of the S-oxides, the appropriate 1,2-benzisothiazol-3-one-1,1-dioxide nitro derivatives.

TRANSFORMATIONS OF GLYCYRRHIZIC ACID. IX.* SYNTHESIS OF NEW ACYLATES

New esters of a triterpene glycoside, glycyrrhizic acid, were synthesized by acylating the hydroxy groups of the carbohydrate moiety of the acid or its derivatives (trimethyl ester, trisodium, tripotassium, and monoammonium salts) with aromatic acid chlorides.Depending on the reaction conditions and acylating agents, either complete acylation of the acid occurs, or di- or trisubstituted esters and trimethyl ester of glycyrrhizic acid are formed.The following acylates were synthesized: trimethyl di-O-mesityl-, di-O-(o-nitro)benzenesulfonyl-, and penta-O-(p-nitro)-benzoylglycyrrhizates; penta-O-salicyloyl-, -acetylsalicyloyl-, -cinnamoyl-, -(p-methoxy)cinnamoyl-, di-O-(2,4-dinitro)benzoyl-, -isonicotinoyl-, -nicotinoyl-, and tri-O-acetylsalicyloyl-glycyrrhizic acids.