4110-33-2

Basic information

• Product Name: 2 4-DINITROBENZONITRILE 97
• Synonyms: 2 4-DINITROBENZONITRILE 97;Benzonitrile,2,4-dinitro-;2,4-Dinitrobenzonitrile 97%
• CAS NO: 4110-33-2
• Molecular Formula: C₇H₃N₃O₄
• Molecular Weight: 193.11642
• Product Categories: C6 to C7;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 4110-33-2.mol

Chemical Properties

• Melting Point: 100-103 °C(lit.)
• Boiling Point: 395.1°C at 760 mmHg
• Flash Point: 55 °F
• Appearance: /
• Density: 1.55g/cm³
• Vapor Pressure: 1.88E-06mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 2 4-DINITROBENZONITRILE 97(CAS DataBase Reference)
• NIST Chemistry Reference: 2 4-DINITROBENZONITRILE 97(4110-33-2)
• EPA Substance Registry System: 2 4-DINITROBENZONITRILE 97(4110-33-2)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22
• Safety Statements: 16-36
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 4110-33-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,4-Dinitrobenzonitrile is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals. Its unique structure allows for further functionalization and modification, making it a versatile building block in organic chemistry.
Used in the Synthesis of N′-hydroxy-2,4-dinitrobenzimidamide:
One specific application of 2,4-Dinitrobenzonitrile is in the synthesis of N′-hydroxy-2,4-dinitrobenzimidamide, which is an important compound with potential applications in the pharmaceutical industry. The nitro groups in 2,4-Dinitrobenzonitrile can be reduced to hydroxylamine derivatives, which can then be used to form the imidamide structure.
Used in the Chemical Industry:
In the chemical industry, 2,4-Dinitrobenzonitrile can be used as a starting material for the production of various other nitro compounds, which are widely used as intermediates in the synthesis of dyes, plastics, and other materials. Its reactivity and functional groups make it a valuable component in the development of new chemical products.
Used in Research and Development:
Due to its unique chemical properties, 2,4-Dinitrobenzonitrile is also used in research and development for the exploration of new reaction pathways and the discovery of novel compounds with potential applications in various fields, such as pharmaceuticals, materials science, and environmental chemistry.

InChI:InChI=1/C7H3N3O4/c8-4-5-1-2-6(9(11)12)3-7(5)10(13)14/h1-3H

Upstream product

• 18300-85-1 2,4-dinitro-benzenediazonium 
• 3236-33-7 2,4-dinitro-benzaldehyde-oxime 
• 98-10-2 benzenesulfonamide 
• 610-30-0 2,4-dinitrobenzoic acid 
• 584-48-5 2,4-dinitrobromobenzene 
• 544-92-3 copper(I) cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 74381-46-7 2,4-dinitro-benzaldehyde phenylhydrazone 
• 13296-87-2 2,4-dinitrobenzamide 
• 30416-76-3 (benzoylphenylmethylene)triphenylphosphorane 
• 643-43-6 (2,4-dinitro-phenyl)-acetic acid 
• 252929-76-3 (E)-2,4-dinitrobenzaldehyde O-benzoyloxime 
• 60-29-7 diethyl ether 

Downstream Products

• 97112-62-4 2-nitro-4-piperidino-benzonitrile 
• 855290-54-9 4-nitro-2-p-tolylsulfanyl-benzonitrile 
• 855290-55-0 2-nitro-4-p-tolylsulfanyl-benzonitrile 
• 13296-87-2 2,4-dinitrobenzamide 
• 610-30-0 2,4-dinitrobenzoic acid 
• 28340-71-8 4-morpholin-4-yl-2-nitro-benzonitrile 
• 38469-83-9 4-methoxy-2-nitro-benzonitrile 
• 101084-96-2 2-methoxy-4-nitrobenzonitrile 
• 3939-09-1 2,4-difluorobenzonitrile 
• 34667-88-4 2-fluoro-4-nitrobenzonitrile 
• 20350-26-9 2,4-dinitrophenolate 
• 87376-25-8 2-amino-4-nitro-benzonitrile 
• 72115-07-2 4-amino-2-nitrobenzonitrile 
• 836611-13-3 4-nitro-2-(phenylthio)benzonitrile 

Relevant articles and documents

Palladium-Catalyzed Cyanation of Aryl Halides Using Formamide and Cyanuric Chloride as a New “CN” Source

A new source of “CN” employing formamide and cyanuric chloride is introduced for the cyanation reactions. The treatment of formamide and 2,4,6-trichloro-1,3,5-triazine (TCT; cyanuric chloride) afforded an efficient cyanating agent which it can be used as a nontoxic, readily available, and non-expensive reagent in the cyanation transformations. In this study, palladium-catalyzed cyanation of aryl halides was successfully accomplished using this new “CN” source in high yields.

Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS): An efficient catalyst for cyanation reaction in aqueous media

Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS) were found to be an efficient heterogeneous catalyst in the cyanation reaction of aryl halides in aqueous media. This catalyst system is containing palladium nanoparticles with a size of ～7 nm. Moreover, the CD-PU-NS support formed microsphere-shaped structures with a size of ～100–200 nm. The TEM images show that Pd nanoparticles were formed in near spherical shape morphology and were immobilized in the structure of the CD-PU-NS support. Under our optimized reaction conditions, aryl cyanides were obtained in high yields in the presence of the Pd-CD-PU-NS catalyst. Our results demonstrated that the Pd-CD-PU-NS catalyst is highly effective in the cyanation reaction in aqueous media. Furthermore, the catalyst could be simply extracted from the reaction mixture, providing an efficient methodology for the synthesis of aryl cyanides. The Pd-CD-PU-NS catalyst could be recycled four times with almost consistent catalytic efficiency.

Cyanation of aromatic/vinylic boronic acids with α-cyanoacetates

A friendly protocol is reported to achieve cyanation of aromatic and vinylic boronic acids using nontoxic and readily available α-cyanoacetates as a cyano source under aerobic conditions. Many aryl/vinyl boronic acids (as well as some iodides and bromides) are amenable substrates to give aryl nitriles and acrylonitriles. This cyanation method provides a safe and operationally convenient alternative to traditional ones requiring toxic cyanide salts.

Eliminations from (E)-2,4-dinitrobenzaldehyde O-aryloximes promoted by R3N/R3NH+ in 70 mol% MeCN(aq). Effects of leaving group and base-solvent on the nitrile-forming transition-state

Elimination reactions of (E)-2,4-(NO2)2C 6H2CH=NOC6H3-2-X-4-NO2 (1a-e) promoted by R3N/R3NH+ in 70 mol % MeCN(aq) have been studied kinetically. The reactions are second-order and exhibit Broensted β = 0.80- 0.84 and |βlg| = 0.39-0.42, respectively. For all leaving groups and bases employed in this study, the β and |βlg| values remained almost the same. The results can be described by a negligible pxy interaction coefficient, pxy = δβ/pKlg = δβlg/pK-azip 0, which describes the interaction between the base catalyst and the leaving group. The negligible pxy interaction coefficient is consistent with the (E1cb) irr mechanism. Change of the base-solvent system from R 3N/MeCN to R3N/R3NH+-70 mol % MeCN(aq) changed the reaction mechanism from E2 to (E1cb)irr. Noteworthy was the relative insensitivity of the transition state structure to the reaction mechanism change.

An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes: A mechanistic perception

While attempting to synthesize nitriles from aldoximes using O-sulfonate esters of oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate], an unexpected involvement of oxyma cleaved product in promoting the synthesis of nitriles was observed. Such involvement of the oxyma cleaved product in the reaction mechanism, together with the usual anticipated pathway improved drastically the applicability of the method by reducing the time needed for the reaction to be completed over that of the sulfonyl chlorides. Other advantages of the present protocol are excellent yields in ambient and milder conditions.

Eliminations from (E)-2,4-dinitrobenzaldehyde O-aryloximes promoted by R3N in MeCN. Effects of β-aryl group and base-solvent on the nitrile-forming transition-state

Nitrile-forming eliminations from (E)-2,4-(NO2)2C 6H 2CH=NOC 6H 4-2-X-4-NO2 (1a-e) promoted by R 3N in MeCN have been studied kinetically. The reactions are second-ord

Elimination of nitrile from (E)-2,4,6-trinitrobenzaldehyde O-pivaloyloxime promoted by R2NH in MeCN. Effect of β-aryl group on the nitrile-forming transition-state

Nitrile-forming eliminations from (E)-2,4,6-(NO2) 3C6H2CH=NOC(O)(CH3)3 promoted by R2NH in MeCN have been studied kinetically. The reactions are second-order and exhibit substantial Hammett ρ and Broensted β values. The k 2 value for elimination from (E)-2,4,6- trinitrobenzaldehyde O-pivaloyloxime promoted by i-Pr2NH in MeCN falls on a single line in the Hammett plot for different β-aryl substituents, which have been shown to react by the E2 mechanism. This result indicated that the reaction mechanism is not changed by the introduction of the 2,4,6-trinitro substituents, and that the elimination reactions from (E)-benzaldehyde O-pivaloyloximes series proceed by the common E2 mechanism.

Straightforward conversion of arene carboxylic acids into aryl nitriles by palladium-catalyzed decarboxylative cyanation reaction

A one-pot procedure to convert aromatic carboxylic acids into aromatic nitriles is described. The methodology is based on a palladium(II)-catalyzed decarboxylative cyanation reaction using cyanohydrins as soluble cyanide sources. The described reaction worked on a panel of substrates and is additionally of particular interest for the straightforward preparation of 13C- or 14C-labeled compounds.

Elimination reactions of (E)-2,4-dinitrobenzaldehyde O-benzoyloximes promoted by R2NH/R2NH2+ in 70 mol % MeCN(aq). Change of reaction mechanism

(Chemical Equation Presented) Elimination reactions of (E)-2,4-(NO 2)2C6H3CH=NOC(O)-C6H 4X (1) promoted by R2NH/R2NH2 + in 70 mol % MeCN(aq) have been studied kinetically. The reactions are second-order and exhibit Broensted β = 0.27-0.32 and |βlg| = 0.28-0.32. The result can be described by a negligible Pxy interaction coefficient, pxy = ?β/ ?pKlg = ?βlg/?pKBH ≈ 0, which describes the interaction between the base catalyst and the leaving group. The negligible pxy coefficients are consistent with the (E1cb) irr mechanism.

From aldehydes to nitriles, a general and high yielding transformation using HOF·CH3CN complex

N,N-Dimethylhydrazones of aldehydes undergo a rapid oxidative cleavage to form nitriles in very high yields on reaction with HOF·CH3CN under mild conditions. The reaction is chemoselective and proceeds rapidly without racemization. The nitriles were resistant to further oxidation, even when a large excess of the reagent was employed.