4-Amino-N,N-dimethyl-3-nitroaniline

Base Information

• Chemical Name: 4-Amino-N,N-dimethyl-3-nitroaniline
• CAS No.: 16293-12-2
• Molecular Formula: C8H11N3O2
• Molecular Weight: 181.194
• Hs Code.: 29214200
• European Community (EC) Number: 821-124-9
• DSSTox Substance ID: DTXSID30369915
• Nikkaji Number: J82.495J
• Wikidata: Q72440012
• Mol file: 16293-12-2.mol

Synonyms:16293-12-2;4-Amino-N,N-dimethyl-3-nitroaniline;N1,N1-Dimethyl-3-nitrobenzene-1,4-diamine;4-Amino-3-nitro-N,N-dimethylaniline;4-N,4-N-dimethyl-2-nitrobenzene-1,4-diamine;1,4-Benzenediamine, N4,N4-dimethyl-2-nitro-;4-(Dimethylamino)-2-nitroaniline;SCHEMBL976044;DTXSID30369915;COWGRITUYIECBW-UHFFFAOYSA-N;4-Dimethylamino-2-nitrobenzenamine;MFCD00845876;AKOS015888786;AS-65712;BP-20110;CS-0187567;FT-0617584;N4,N4-dimethyl-2-nitrobenzene-1,4-diamine;N-(4-amino-3-nitrophenyl)-N,N-dimethylamine;C73135;A810424;AH-034/32470033;N~4~,N~4~-dimethyl-2-nitro-1,4-benzenediamine;J-640212;J-800214

Chemical Property of 4-Amino-N,N-dimethyl-3-nitroaniline

Chemical Property:

• Appearance/Colour: black crystalline powder
• Vapor Pressure: 0.00012mmHg at 25°C
• Melting Point: 112-122 °C
• Refractive Index: 1.645
• Boiling Point: 335.433 °C at 760 mmHg
• PKA: 4.15±0.22(Predicted)
• Flash Point: 156.664 °C
• PSA: 75.08000
• Density: 1.28 g/cm³
• LogP: 2.34740
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 181.085126602
• Heavy Atom Count: 13
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

4-(Dimethylamino)-2-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• 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)[N+](=O)[O-]

Technology Process of 4-Amino-N,N-dimethyl-3-nitroaniline

There total 6 articles about 4-Amino-N,N-dimethyl-3-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: 75.0%

N'-acetyl-N,N-dimethyl-1,4-phenylenediamine (7463-28-7) → N4,N4-Dimethyl-2-nitro-1,4-phenylenediamine (16293-12-2)

Guidance literature:

N'-acetyl-N,N-dimethyl-1,4-phenylenediamine; With sulfuric acid; nitric acid; at 0 - 20 ℃;

With water; sodium hydroxide; for 1h; Reflux;

DOI:10.1002/zaac.202000461

Reference yield:

dimethylaminoboronic acid + 5-bromo-2-nitroaniline (5228-61-5) → N4,N4-Dimethyl-2-nitro-1,4-phenylenediamine (16293-12-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate;

DOI:10.1016/j.bmcl.2013.07.001

Reference yield:

N,N-dimethyl-3-nitroaniline (619-31-8) → N4,N4-Dimethyl-2-nitro-1,4-phenylenediamine (16293-12-2) + N2,N2-Dimethyl-4-nitro-1,2-phenylenediamine (5367-53-3) + N1,N1-Dimethyl-3-nitro-1,2-phenylenediamine

Guidance literature:

With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride; In N,N-dimethyl-formamide; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo951903r

upstream raw materials:

4-N,N-dimethylamino-2-nitroacetanilide

N,N-dimethyl-3-nitroaniline

5-bromo-2-nitroaniline

4-amino-N,N-dimethylaniline

Downstream raw materials:

C₁₇H₂₇N₃O₃

N⁴,N⁴-dimethyl-1,2,4-benzenetriamine

Refernces

• 1、 Wang, Tong,Sepulveda, Mario,Gonzales, Paul,Gately, Stephen. "Identification of novel HDAC inhibitors through cell based screening and their evaluation as potential anticancer agents". . p. 4790 - 4793. Retrieved 2013/09/02.
• 2、 Seko, Shinzo,Kawamura, Norio. "Copper-catalyzed direct amination of nitrobenzenes with O-alkylhydroxylamines". . p. 442 - 443. Retrieved 2007/10/02.