N-Methyl-4-nitroaniline

Base Information

• Chemical Name: N-Methyl-4-nitroaniline
• CAS No.: 100-15-2
• Molecular Formula: C7H8N2O2
• Molecular Weight: 152.153
• Hs Code.: 29214200
• European Community (EC) Number: 202-823-2
• NSC Number: 5390
• UN Number: 1661
• UNII: J836WLV9BW
• DSSTox Substance ID: DTXSID7025635
• Nikkaji Number: J37.757K
• Wikidata: Q11234217
• ChEMBL ID: CHEMBL1329734
• Mol file: 100-15-2.mol

Synonyms:N-methyl-4-nitroaniline;N-methyl-p-nitroaniline;N-methyl-para-nitroaniline

Chemical Property of N-Methyl-4-nitroaniline

Chemical Property:

• Appearance/Colour: Brownish-yellow crystalline powder
• Vapor Pressure: 0.00205mmHg at 25°C
• Melting Point: 149-151 °C(lit.)
• Refractive Index: 1.619
• Boiling Point: 290.6 °C at 760 mmHg
• PKA: 0.56±0.12(Predicted)
• Flash Point: 129.5 °C
• PSA: 57.85000
• Density: 1.26 g/cm³
• LogP: 2.23270
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 152.058577502
• Heavy Atom Count: 11
• Complexity: 136
• Transport DOT Label: Poison

Purity/Quality:

99.8% ^*data from raw suppliers

N-Methyl-4-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 23/24/25-33-36/37/38
• Safety Statements: 28-36/37/39-45-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitroanilines
• Canonical SMILES: CNC1=CC=C(C=C1)[N+](=O)[O-]
• Uses: N-methyl-4-nitroaniline is a stabilizer for gunpowder, a desensitizing agent for molten cast explosive TNAZ, a widely used organic intermediate, and N-methyl-4-nitroaniline can be used as a reference substance by its polarizing properties. N-methyl-4-nitroaniline is an attractive candidate for its appealing capability to retain the nitrogen oxides, good thermal stability, and facile synthesis from abundant and inexpensive starting materials. N-Methyl-4-nitroaniline is a versatile reactant used in the synthesis of oxindoles using Pd-catalyzed cyclization of chloroacetanilides.

Technology Process of N-Methyl-4-nitroaniline

There total 207 articles about N-Methyl-4-nitroaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

4-nitro-aniline (100-01-6,104810-17-5) + methyl iodide (74-88-4) → N-methyl(p-nitroaniline) (100-15-2)

Guidance literature:

With C₂₄H₅₂B₂₀Cl₂Rh₂Se₂; In toluene; at 20 ℃; for 2h;

Reference yield: 93.0%

4-chlorobenzonitrile (100-00-5) + methylamine (74-89-5) → N-methyl(p-nitroaniline) (100-15-2)

Guidance literature:

In water; for 16h; Pressure bomb;

Reference yield: 79.0%

furan (110-00-9) + N-methyl-4-nitro-N-(phenylthio)benzenamine (110228-59-6) → 2-phenylthiofuran (16003-14-8) + N-methyl-2-(phenylthio)-4-nitroaniline (110228-60-9) + N-methyl(p-nitroaniline) (100-15-2) + diphenyldisulfane (882-33-7)

Guidance literature:

at 85 ℃; for 144h;

upstream raw materials:

N-methyl-4-nitroacetanilide

N-methyl-4-(4-nitrophenyl)formamide

toluene-4-sulfonic acid-(N-methyl-4-nitro-anilide)

4-amino-N,N-dimethylaniline

Downstream raw materials:

3-(N-methyl-4-nitro-anilino)-propane-1,2-diol

N-methyl-4-nitroacetanilide

N-[(4-chloro-phenylsulfanyl)-methyl]-N-methyl-4-nitro-aniline

N-(4-nitrophenyl)-N,2-dimethylcyclohex-1-en-1-amine

Refernces

• 1、 Al-Kaabi, Sharifa S.,Hallett, Geoffrey,Meyer, Thomas A.,Williams, D. Lyn H.. "Unusual Rate-limiting Proton Transfer in the Acid-catalysed Reactions of N-Nitroso Compounds". . p. 1803 - 1808. Retrieved 1984.
• 2、 Grossi, Loris,Montevecchi, Carlo. "The Reaction of Benzenesulfenanilides with Lewis Acids: Involvement of Radical Cation Intermediates.". . p. 9095 - 9104. Retrieved 1993.
• 3、 Baciocchi, Enrico,Gerini, Maria Francesca,Lanzalunga, Osvaldo,Lapi, Andrea,Mancinelli, Simona,Mencarelli, Paolo. "Oxidative N-demethylation of N,N-dimethylanilines catalysed by lignin peroxidase: A mechanistic insight by a kinetic deuterium isotope effect study". . p. 393 - 394. Retrieved 2000.
• 4、 Leischner, Thomas,Artús Suarez, Lluis,Spannenberg, Anke,Junge, Kathrin,Nova, Ainara,Beller, Matthias. "Highly selective hydrogenation of amides catalysed by a molybdenum pincer complex: Scope and mechanism". . p. 10566 - 10576. Retrieved 2019.
• 5、 Yurovskaya,Ivanenkov,Starkova. "New transformation of 2-substituted 5-nitropyrimidines by the action of the enamine form of N-methylacetone imine [4]". . p. 1140 - 1141. Retrieved 2002.
• 6、 Baciocchi, Enrico,Lanzalunga, Osvaldo,Lapi, Andrea,Manduchi, Laura. "Kinetic deuterium isotope effect profiles and substituent effects in the oxidative N-demethylation of N,N-dimethylanilines catalyzed by tetrakis(pentafluorophenyl)porphyrin iron(III) chloride". . p. 5783 - 5787. Retrieved 1998.
• 7、 Sun, Nan,Wang, Shuai,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan. "A facile protocol for the synthesis of mono-N-methyl anilines via formimidate intermediates". . p. 7142 - 7148. Retrieved 2010.
• 8、 Khazipova, A. N.,Khusnutdinov, R. I.,Mayakova, Yu. Yu.,Shchadneva, N. A.. "Methoxycarbonylation of Alkyl-, Cycloalkyl-, and Arylamines with Dimethyl Carbonate in the Presence of Binder-Free Zeolite". . p. 1228 - 1235. Retrieved 2020.
• 9、 Gromov, S. P.. "Formation of anilines from 5-nitro-2-phenylpyrimidine, amines, and acetone". . p. 1041 - 1043. Retrieved 1994.
• 10、 Yan, Huidong,Zeng, Liufang,Xie, Yaqiang,Cui, Yu,Ye, Liyi,Tu, Song. "N-Methylation of poorly nucleophilic aromatic amines with dimethyl carbonate". . p. 5951 - 5960. Retrieved 2016.