N,N-Dimethyl-4-nitroaniline

Base Information

• Chemical Name: N,N-Dimethyl-4-nitroaniline
• CAS No.: 100-23-2
• Deprecated CAS: 508191-95-5
• Molecular Formula: C8H10N2O2
• Molecular Weight: 166.18
• Hs Code.: 29214200
• European Community (EC) Number: 202-832-1
• NSC Number: 9815
• UNII: H347TX7J9K
• DSSTox Substance ID: DTXSID4059209
• Nikkaji Number: J29.608B
• Wikidata: Q63398957
• ChEMBL ID: CHEMBL3098161
• Mol file: 100-23-2.mol

Synonyms:N,N-dimethyl-4-nitroaniline;N,N-dimethyl-p-nitroaniline;p-N,N-dimethylnitroaniline

Chemical Property of N,N-Dimethyl-4-nitroaniline

Chemical Property:

• Appearance/Colour: Yellow Solid
• Vapor Pressure: 0.00247mmHg at 25°C
• Melting Point: 163-165 °C
• Refractive Index: 1.6273 (estimate)
• Boiling Point: 287.6°Cat760mmHg
• PKA: 0.74±0.12(Predicted)
• Flash Point: 127.7°C
• PSA: 49.06000
• Density: 1.193g/cm³
• LogP: 2.18400
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Dichoromethane (Slightly)
• Water Solubility.: Soluble in dichloromethane. Insoluble in water. Solubility in hot methanol (almost transparency).
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 166.074227566
• Heavy Atom Count: 12
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

N,N-Dimethyl-4-nitroaniline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 36/37/38-23/24/25
• Safety Statements: 45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)[N+](=O)[O-]
• Uses: It is an aromatic intermediate and in the experimental and theoretical study of the structure of N,N-dimethyl-4-nitroaniline derivatives as model compounds for non-linear optical organic materials.

Technology Process of N,N-Dimethyl-4-nitroaniline

There total 135 articles about N,N-Dimethyl-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: 100.0%

p-nitro-N,N-dimethylaniline-N-oxide (26492-31-9) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + N,N-Dimethyl-4-nitroaniline (100-23-2)

Guidance literature:

With 1H-imidazole; meso-tetraphenylporphyrin iron(III) chloride; DMA-OCH₃; In chloroform; at 25 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)84329-4

Reference yield: 96.0%

p-nitro-N,N-dimethylaniline-N-oxide (26492-31-9) → N,N-Dimethyl-4-nitroaniline (100-23-2)

Guidance literature:

With phenylboronic acid; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1016/j.tetlet.2017.01.051

Reference yield: 73.0%

4-nitro-aniline (100-01-6,104810-17-5) + methyl iodide (74-88-4) → N,N-Dimethyl-4-nitroaniline (100-23-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2013.09.031

upstream raw materials:

N,N-dimethylaniline N-oxide

4-bromo-N,N-dimethylaniline

4-Iodo-N,N-dimethylaniline

1,1-bis-(4-dimethylamino-phenyl)-ethane

Downstream raw materials:

4-<(p-dimethylaminophenyl)azo>pyridine

pyridine-azo-p-dimethyl aniline

N,N-dimethyl-4-(1-oxy-pyridin-2-ylazo)-aniline

4-dimethylaminobenzeneazo-2-naphthalene

Refernces

• 1、 Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Salehian, Fatemeh,Fazli, Kazem. "Safe and efficient reductive methylation of primary and secondary amines using N-methylpyrrolidine zinc borohydride". . p. 2415 - 2420. Retrieved 2010.
• 2、 Chehardoli, Gholamabbas,Azimi, Seyedeh Bahareh. "Melamine-(H2SO4)3/Melamine-(HNO3)3 Instead of H2SO4/HNO3: Benign System for Oxidation/Nitration Reactions from in situ NO2 +". . p. 589 - 594. Retrieved 2019.
• 3、 Davies, Ian W.,Marcoux, Jean-Francois,Kuethe, Jeffery T.,Lankshear, Michael D.,Taylor, Jeremy D. O.,Tsou, Nancy,Dormer, Peter G.,Hughes, David L.,Houk,Guner, Vildan. "Demonstrating the Synergy of Synthetic, Mechanistic, and Computational Studies in A Regioselective Aniline Synthesis". . p. 1298 - 1308. Retrieved 2004.
• 4、 Chiranjeevi, Barreddi,Koyyada, Ganesh,Prabusreenivasan,Kumar, Vanaja,Sujitha, Pombala,Kumar, C. Ganesh,Sridhar,Shaik, Saida,Chandrasekharam, Malapaka. "Iron-catalyzed aryl-aryl cross coupling route for the synthesis of 1-(2-amino)-phenyl)dibenzo[b,d]furan-2-ol derivatives and their biological evaluation". . p. 16475 - 16485. Retrieved 2013.
• 5、 Minero, Claudio,Lucchiari, Mirco,Maurino, Valter,Vione, Davide. "A quantitative assessment of the production of OH and additional oxidants in the dark Fenton reaction: Fenton degradation of aromatic amines". . p. 26443 - 26450. Retrieved 2013.
• 6、 Huang, Yan,Deng, Wei,Lin, Bo-Lin. "Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis". . . Retrieved 2019.
• 7、 Kirby,Jencks. "-". . p. 3209,3210. Retrieved 1965.
• 8、 Campbell. "-". . p. 740. Retrieved 1949.
• 9、 Amal Joseph,Priyadarshini,Lakshmi Kantam,Maheswaran. "Copper catalyzed ipso-nitration of iodoarenes, bromoarenes and heterocyclic haloarenes under ligand-free conditions". . p. 1511 - 1513. Retrieved 2012.
• 10、 Herzberg,Polonowski. "-". . p. 3201. Retrieved 1891.