2719-15-5

Basic information

• Product Name: 2-METHYL-4-NITROACETANILIDE
• Synonyms: N1-(2-METHYL-4-NITROPHENYL)ACETAMIDE;N-(2-METHYL-4-NITRO-PHENYL)-ACETAMIDE;Acetamide,N-(2-methyl-4-nitrophenyl)-;n-(2-methyl-4-nitrophenyl)-acetamid;2-METHYL-4-NITROACETANILIDE
• CAS NO: 2719-15-5
• Molecular Formula: C₉H₁₀N₂O₃
• Molecular Weight: 194.19
• Mol File: 2719-15-5.mol

Chemical Properties

• Melting Point: 198-200°C
• Boiling Point: 393.3 °C at 760 mmHg
• Flash Point: 191.7 °C
• Appearance: off-white solid
• Density: 1.289 g/cm³
• Vapor Pressure: 2.15E-06mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 2-METHYL-4-NITROACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-4-NITROACETANILIDE(2719-15-5)
• EPA Substance Registry System: 2-METHYL-4-NITROACETANILIDE(2719-15-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• TSCA: Yes
• Hazardous Substances Data: 2719-15-5(Hazardous Substances Data)

Usage

Uses

2'-Methyl-4'-nitroacetanilide acts as the reactant in the synthesis of TNT isomers.

InChI:InChI=1/C9H10N2O3/c1-6-5-8(11(13)14)3-4-9(6)10-7(2)12/h3-5H,1-2H3,(H,10,12)

Upstream product

• 120-66-1 N-(2-methylphenyl)acetamide 
• 108-24-7 acetic anhydride 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 95-53-4 o-toluidine 
• 59907-22-1 N-(2-methyl-6-nitrophenyl)acetamide 
• 108-88-3 toluene 
• 619-15-8 2,5-dinitrotoluene 

Downstream Products

• 56207-35-3 acetic acid-(2-methyl-4,6-dinitro-anilide) 
• 56891-59-9 N-(4-Amino-2-methyl-phenyl)-acetamide 
• 3558-18-7 5-nitro-N-acetylanthranilic acid 
• 609-99-4 3,5-dinitrosalicylic acid 
• 18905-50-5 2-chloro-1-methyl-3,5-dinitrobenzene 
• 609-74-5 1-methyl-2,3,5-trinitrobenzene 
• 6083-69-8 2-Ethoxy-3,5-dinitro-benzoesaeure 
• 609-97-2 2-amino-3,5-dinitro-benzoic acid 
• 7477-94-3 2-methyl-4,6-dinitroaniline 
• 66583-76-4 2-bromo-3,5-dinitro-toluene 
• 102312-37-8 2,3,5-trinitro-benzoic acid 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 54302-37-3 acetic acid-(2,4-diamino-6-methyl-anilide) 
• 87223-52-7 C₁₄H₁₈N₄O₅ 

Relevant articles and documents

Synthesis of indenoquinolinone through aryne-mediated Pd(II)-catalysed remote C–H activation

Abstract: [Figure not available: see fulltext.]Indenoquinolinones have been synthesized from 2-haloquinoline-3-carbaldehyde through Pd-mediated simultaneous C–H (aldehyde) and C–X bond activation. DFT studies were performed to investigate the mechanistic pathway, and in situ UV–Vis studies indicate the presence of Pd(II) intermediate species. Aryne ligated Pd complex is actual intermediate in these reactions. Ligation of reactive aryne to Pd reduces probability of side reactions. Graphic abstract: [Figure not available: see fulltext.]

NOVEL IMIDAZO-PYRAZINE DERIVATIVES

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Biphenyl-Based Bis(thiourea) Organocatalyst for Asymmetric and syn -Selective Henry Reaction

A scalable, efficient and chromatography-free synthesis of a new enantiopure C 2-symmetric bis(thiourea) catalyst was accomplished from a readily available starting material. The developed strategy could be conducted on a multi-gram scale. Both the prepared enantiomers of the bis(thiourea) organocatalyst have been tested in the asymmetric Henry reaction under thoroughly optimized conditions during which an unusual solvent effect on enantioselectivity was found. The corresponding adducts were obtained in excellent yields with good to excellent enantioselectivities. The achieved high reactivity and enantioselectivity in the nitroaldol reaction of nitroalkanes with aromatic aldehydes suggests promising potential for this catalyst. Moreover, a significant syn-diastereoselectivity was observed.

Selectivity of the complexation reactions of four regioisomeric methylcamphorquinoxaline ligands with gold(III): X-ray, NMR and DFT investigations

Reported are the synthesis, spectral and structural characteristics of new quinoxaline-related regioisomeric ligands L1-L4 (1,x,11,11-tetramethyl-1,2,3,4-tetrahydro-1,4-methanophenazine, x = 7, 8, 9 and 6, respectively) and their mononuclear Au(III) complexes (1-4). Fusion of the camphor moiety to the quinoxaline core made two N-atoms of quinoxaline nonequivalent while the introduction of a methyl-substituent at positions 6-9 enabled a tuning of coordination properties of L1-L4. Gold(III) complexes 1-4 and ligands L1-L4 have been studied in detailed by 1D and 2D NMR and the structures of 1-4 have been determined by X-ray crystallography. The results of these analyses revealed a regiospecific coordination of Au(III) to the sterically less hindered N-5 atom (spatially close to the non-substituted bridgehead carbon) of L1-L3, and to N-10 (spatially close to the methyl-substituted bridgehead carbon) of L4. The results of DFT calculations shed light on disparate coordination modes of L1-L4 toward the AuCl3 fragment and explain formation of single coordination products in high yield.

Synthesis method of 2-methyl-4-nitrobenzoic acid

The invention discloses a synthesis method of 2-methyl-4-nitrobenzoic acid, and belongs to the technical field of chemosynthesis. According to the method, methylbenzene is used as raw materials; reaction liquid formed by mixing concentrated nitric acid and concentrated sulfuric acid is added for mixing; after being washed by a sodium hydroxide solution, the materials take an reaction with stannous chloride, iron powder and glacial acetic acid; then, hydrochloric acid is dropwise added for mixing to obtain 2-amino-5-nitrotoluene; then, the 2-amino-5-nitrotoluene is mixed with acetic acid and the concentrated sulfuric acid for taking a reaction; after the oxidization by an oxidizing agent of sodium perborate, temperature lowering by ice water and washing by deionized water are carried out; then, under the oxidization effect of an oxidizing agent of potassium permanganate, the materials are mixed with hydrochloric acid for reaction; then, still standing, suction filtering and drying are carried out, and the 2-methyl-4-nitrobenzoic acid is obtained. The synthesis method has the beneficial effects that the synthesis process is simple; the cost is low; byproducts are few; the yield of obtained products is as high as more than 95 percent; the purity is as high as more than 99 percent.

Ozone-mediated Reaction of Anilides and Phenyl Esters with Nitrogen Dioxide: Enhanced Ortho-reactivity and Mechanistic Implications

In the presence of ozone, anilides 1 can be nitrated rapidly with nitrogen dioxide in chloroform at 0 deg C to give a high proportion of ortho-nitro derivatives (ortho:para = 1.2-4.4) in good yields.The phenyl esters 15 can be similarly nitrated on the aromatic ring without significant cleavage of the ester bond, giving a mixture of isomeric nitro derivatives in which the ortho-isomer predominantes (ortho:para = 1.1-1.5).The oridin of the enhanced ortho reactivity is discussed in terms of an electron-transfer process involving the nitrogen trioxide as initial electrophile.

Ortho-Selective Nitration of Acetanilides with Nitrogen Dioxide in the Presence of Ozone

In the presence of ozone, nitrogen dioxide rapidly reacts with acetanilides ortho-selectively at low temperatures, giving a high proportion of ortho-nitro derivatives in good yields.

Ruthenium-optically active phosphine complex

A ruthenium-optically active phosphine complex having, as a ligand, BICHEP which means 2,2'-bis(dicyclohexylphosphino)-6,6'-dimethyl-1,1'-biphenyl represented by formula (I): STR1 is disclosed, which can catalyze asymmetric syntheses, such as asymmetric hydrogenation, asymmetric isomerization, and asymmetric silylation, exhibiting excellent catalytic activity and providing high optical purity.

Process for preparing 4-amino-3-methyl-N-substituted or unsubstituted alkylanilines

A process for the preparation of 4-amino-3-methyl-N-substituted or unsubstituted alkylanilines comprising acylating and/or sulfonylating 4-amino-3-methyl-nitro-benzene having the formula (I) STR1 with an acylation or sulfonylation agent to obtain a compound having the general formula (II) STR2 wherein R1 represents a hydrogen atom or an acyl group, R2 represents an acyl group or a sulfonyl group, or R1 and R2 can combine as a difunctional acyl group; reducing the nitro group of the compound having the general formula (II) with hydrogen in the presence of a metal hydrogenation catalyst to obtain a compound having the general formula (III) STR3 wherein R1 and R2 are as above defined; alkylating the amino group of the compound having the general formula (III) with an alkylation agent selected from the group consisting of an alkyl halide, a substituted alkyl halide and an alkylene oxide to obtain a compound having the general formula (IV) STR4 wherein R1 and R2 are as above defined, R3 represents an alkyl group or a substituted alkyl group and R4 represents a hydrogen atom, an alkyl group or a substituted alkyl group; and hydrolyzing the compound having the general formula (IV) to obtain a compound having the general formula (V) STR5 wherein R3 and R4 are as above defined.