2216-16-2

Basic information

• Product Name: 3-DIETHYLAMINO-1-NITROBENZENE
• Synonyms: 3-DIETHYLAMINO-1-NITROBENZENE;3-Nitro-N,N-diethylaniline;TIMTEC-BB SBB008082;N,N-DIETHYL-3-NITROANILINE;N N-DIETHYL-M-NITROANILINE;m-Nitrodiethylaniline;Benzenamine, N,N-diethyl-3-nitro-;n,n-diethyl-3-nitro-benzenamin
• CAS NO: 2216-16-2
• Molecular Formula: C₁₀H₁₄N₂O₂
• Molecular Weight: 194.23
• Mol File: 2216-16-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 77.5°C (estimate)
• Boiling Point: 289.05°C
• Flash Point: 135.7 °C
• Appearance: /
• Density: 1.127
• Vapor Pressure: 0.00226mmHg at 25°C
• Refractive Index: 1.6358 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.22±0.30(Predicted)
• CAS DataBase Reference: 3-DIETHYLAMINO-1-NITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-DIETHYLAMINO-1-NITROBENZENE(2216-16-2)
• EPA Substance Registry System: 3-DIETHYLAMINO-1-NITROBENZENE(2216-16-2)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 2216-16-2(Hazardous Substances Data)

Usage

General Description

3-Diethylamino-1-nitrobenzene is a chemical compound with the molecular formula C10H14N2O2. It is a yellow crystalline solid with a strong odor, and it is commonly used as an intermediate in the synthesis of various pharmaceuticals and dyes. 3-DIETHYLAMINO-1-NITROBENZENE is toxic if ingested or inhaled, and it may cause irritation to the skin and eyes upon contact. It is also known to be highly flammable. In addition, 3-diethylamino-1-nitrobenzene is classified as a hazardous substance due to its potential environmental and health risks, and proper safety measures should be taken when handling and storing this chemical.

InChI:InChI=1/C10H14N2O2/c1-3-11(4-2)9-6-5-7-10(8-9)12(13)14/h5-8H,3-4H2,1-2H3

Upstream product

• 75-03-6 ethyl iodide 
• 99-09-2 3-nitro-aniline 
• 91-66-7 N,N-diethylaniline 
• 64-67-5 diethyl sulfate 
• 98-88-4 benzoyl chloride 
• 24163-36-8 3,3'-dinitrodiphenyliodonium bromide 
• 109-89-7 diethylamine 
• 586-78-7 para-nitrophenyl bromide 
• 645-00-1 m-iodonitrobenzene 
• 75-07-0 acetaldehyde 

Downstream Products

• 26513-20-2 N,N-diethyl-1,3-benzenediamine 
• 52603-47-1 m-diethylaminomethanesulfonanilide 
• 76751-15-0 3-Valeramido-N,N-diethyl-anilin 
• 79811-41-9 Pentanoic acid [2-(2,6-dicyano-4-nitro-phenylazo)-5-diethylamino-phenyl]-amide 
• 22185-75-7 N,N-diethyl-N'-propionyl-1,3-benzenediamine 
• 32763-28-3 N,N-diethyl-N'-(p-toluenesulfonyl)-1,3-benzenediamine 

Relevant articles and documents

A Phosphine-Mediated Dearomative Skeletal Rearrangement of Dianiline Squaraine Dyes

A phosphorus(III)-mediated dearomatization of ortho-substituted dianiline squaraine dyes results in an unusual skeletal rearrangement to provide exotic, highly conjugated benzofuranone and oxindole scaffolds bearing a C3 side chain comprised of a linear conflagration of an enol, a phosphorus ylide, and 2,4-disubstituted aniline. Employing experimental and computational analysis, a mechanistic evaluation revealed a striking dependence on the acidity of the aniline ortho substituent. Notably, the rearrangement adducts underwent rapid and complete reversion to the parent squaraine in the presence of a Br?nsted acid.

Discovery of Potent, Selective Stem Cell Factor Receptor/Platelet Derived Growth Factor Receptor Alpha (c-KIT/PDGFRα) Dual Inhibitor for the Treatment of Imatinib-Resistant Gastrointestinal Stromal Tumors (GISTs)

Stem cell factor receptor (c-KIT) and platelet derived growth factor receptor alpha (PDGFRα) kinases play an important role in gastrointestinal stromal tumors (GISTs). Here, we have discovered an c-KIT/PDGFRα dual inhibitor, compound 31, with single-digit nanomolar potency against c-KIT and PDGFRα. Compared to Imatinib (1), 31 showed better antiproliferative efficacy against various TEL-c-KIT/PDGFRα-BaF3 isogenic cells, including three 1-resistant BaF3 cell lines, as well as against GIST-T1 and GIST-882 cell lines. Furthermore, compound 31 showed a good KinomeScan selectivity (468 kinases) (S score (1) = 0.01 at 1 μM concentration), good metabolic stability in liver microsomes, and no hERG inhibitory activity. It was worth noting that 31 inhibited GIST-T1 tumor growth (TGI = 81.5%) and even the BaF3-TEL-cKIT-T670I tumor progression (TGI = 41.9%, 1-resistant GISTs) at a dosage of 100 mg/kg/day without exhibiting apparent toxicity.

Amination of aryl bromides catalysed by supported palladium

Palladium particles immobilised onto a metal oxide support or Pd(0), Pd(II) and [Pd(NH3)4]2+ in NaY zeolite have been prepared and characterised. They exhibit a good activity towards the amination of aryl bromides using secondary amines such as piperidine and diethyl amine with a good regio-selectivity for these reactions. Low Pd concentrations (1 mol%) are required to observe a reasonable regio-selectivity. The catalysts can easily be separated from the reaction mixture (filtration) and reused without loss of activity and selectivity. The electronic nature of the aryl halides plays an important role for both the reaction yields and the regio-control of the reaction. It depends on the relation of the direct amination via a benzyne intermediate versus the Pd-catalysed route.