N,N-Diethyl-P-phenylenediamine

Base Information

• Chemical Name: N,N-Diethyl-P-phenylenediamine
• CAS No.: 93-05-0
• Molecular Formula: C10H16N2
• Molecular Weight: 164.25
• Hs Code.: 29215190
• European Community (EC) Number: 202-214-1
• NSC Number: 147488
• UN Number: 1673
• UNII: 0QQA4DFV2J
• DSSTox Substance ID: DTXSID2025058
• Nikkaji Number: J28.419J
• Wikipedia: Color_Developing_Agent_1
• Wikidata: Q3032706
• ChEMBL ID: CHEMBL1452158
• Mol file: 93-05-0.mol

Synonyms:4-amino-N,N-diethylaniline;4-amino-N,N-diethylaniline sulfate;N,N-diethyl 4-phenylenediamine;N,N-diethyl 4-phenylenediamine hydrochloride;N,N-diethyl 4-phenylenediamine monohydrochloride;N,N-diethyl 4-phenylenediamine oxalate (2:1);N,N-diethyl 4-phenylenediamine sulfate;N,N-diethyl 4-phenylenediamine sulfate (1:1);N,N-diethyl p-phenylenediamine;N,N-diethyl-1,4-phenylenediamine;N,N-diethyl-p-phenylenediamine

Chemical Property of N,N-Diethyl-P-phenylenediamine

Chemical Property:

• Appearance/Colour: yellow to brown solid or liquid
• Melting Point: 19-21 °C(lit.)
• Refractive Index: n20/D 1.571(lit.)
• Boiling Point: 261 °C at 760 mmHg
• PKA: 8.21±0.32(Predicted)
• Flash Point: 108.9 °C
• PSA: 29.26000
• Density: 1.009 g/cm³
• LogP: 2.69620
• Storage Temp.: Freezer
• Solubility.: water: insoluble
• Water Solubility.: <0.1 g/100 mL at 19 oC
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 164.131348519
• Heavy Atom Count: 12
• Complexity: 113
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

N1,N1-diethyl-1,4-Benzenediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-34
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CCN(CC)C1=CC=C(C=C1)N
• Uses: Dye intermediate, source of diazonium compounds in diazo copying process. N,N-Diethyl-p-phenylenediamine has been employed as a reference probe to investigate rapid chlorination rate constants by a stopped-flow spectrophotometric competition kinetics method.

Technology Process of N,N-Diethyl-P-phenylenediamine

There total 36 articles about N,N-Diethyl-P-phenylenediamine 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: 99.0%

2-[(4-diethylaminophenylamino)methylene]malonic acid diethyl ester (104007-17-2) → N,N-diethylaniline (93-05-0)

Guidance literature:

With ethylenediamine; In ethanol; at 20 ℃; for 0.25h;

DOI:10.1002/chem.200902054

Reference yield: 86.0%

N,N-diethyl-4-nitrosoaniline (120-22-9) → N,N-diethylaniline (93-05-0)

Guidance literature:

With ammonium chloride; aluminium; In methanol; for 5h; Heating;

Reference yield: 67.0%

N,N-diethyl-4-nitrosoaniline (120-22-9) → C20H30N4 + N,N-diethylaniline (93-05-0)

Guidance literature:

With potassium hydroxide; aluminium; In methanol; at 20 ℃; for 0.25h;

upstream raw materials:

N,N-diethyl-4-nitrosoaniline

4,4'-Bis-diaethylamino-azobenzol

C₁₉H₁₉N₃O₂

4-diethylamino-4'-nitroazobenzene

Downstream raw materials:

N-((p-diethylamino)phenyl)phthalimide

N-(4-diethylamino-anilinomethyl)-phthalimide

4-(4-diethylamino-phenylimino)-5-phenyl-2,4-dihydro-pyrazol-3-one

4-Diethylamino-phenylimino-3-methyl-1-phenyl-2-pyrazolin-5-on

Refernces

Reductive Lithiation in the Absence of Aromatic Electron Carriers. A Steric Effect Manifested on the Surface of Lithium Metal Leads to a Difference in Relative Reactivity Depending on Whether the Aromatic Electron Carrier Is Present or Absent

10.1021/acs.joc.5b01136

The research focuses on reductive lithiation, a method for preparing organolithium compounds, typically involving the use of aromatic radical-anions or lithium metal in the presence of an aromatic electron transfer catalyst. The study explores the reductive lithiation of alkyl phenyl thioethers, alkyl chlorides, acrolein diethyl acetal, and isochroman using lithium dispersion as a source of lithium metal, absent of an electron transfer agent. The experiments involved various substrates with different alkyl group sizes to investigate the steric effect on the reaction's efficiency and selectivity. The analyses included DFT calculations to understand the bond dissociation energies and adsorption geometries on the lithium surface, as well as traditional organic chemistry techniques such as NMR spectroscopy and mass spectrometry to characterize the products and monitor the progress of the reactions. The results showed that lithium dispersion could achieve reductive lithiation efficiently and that the reactivity order was reversed when comparing the presence or absence of an electron transfer agent, with smaller alkyl groups exhibiting greater reactivity. This discovery challenges the prevailing understanding of reductive lithiation and highlights the significance of steric effects in these reactions.