619-31-8

Basic information

• Product Name: N,N-DIMETHYL-3-NITROANILINE
• Synonyms: 1-(Dimethylamino)-3-nitrobenzene;Aniline, N,N-dimethyl-m-nitro-;Benzene, 1-(dimethylamino)-3-nitro-;m-Nitro-N,N-dimethylaniline;n,n-dimethyl-3-nitro-benzenamin;N,N-Dimethyl-3-nitrobenzenamine;N,N-DIMETHYL-3-NITROANILINE;N,N-DIMETHYL-M-NITROANILINE
• CAS NO: 619-31-8
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• EINECS: 210-590-3
• Product Categories: Aromatics Compounds;Aromatics;Intermediates
• Mol File: 619-31-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 57-61 °C
• Boiling Point: 280 °C
• Flash Point: 117 °C
• Appearance: Orange to orange-red/Crystals or Crystalline Powder
• Density: 1.3130
• Vapor Pressure: 0.00334mmHg at 25°C
• Refractive Index: 1.6343 (estimate)
• PKA: 2.62(at 25℃)
• BRN: 1841745
• CAS DataBase Reference: N,N-DIMETHYL-3-NITROANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYL-3-NITROANILINE(619-31-8)
• EPA Substance Registry System: N,N-DIMETHYL-3-NITROANILINE(619-31-8)

Safety Data

• Hazard Codes: T,Xn
• Statements: 36/37/38-23/24/25
• Safety Statements: 45-36/37/39-26-36/37
• RIDADR: 2811
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 619-31-8(Hazardous Substances Data)

Usage

Chemical Properties

Red Cyrstalline Solid

Purification Methods

Crystallise the aniline from EtOH. The picrate has m 119o (from EtOH). [Beilstein 12 H 701, 12 III 1544, 12 IV 1591.]

InChI:InChI=1/C8H10N2O2/c1-9(2)7-4-3-5-8(6-7)10(11)12/h3-6H,1-2H3

Upstream product

• 20129-83-3 4-dimethylamino-2-nitro-benzoic acid 
• 109384-41-0 N,N-dimethyl-3-nitroaniline N-oxide 
• 27389-55-5 N,N,N-trimethyl-3-nitroanilinium iodide 
• 151-18-8 2-cyanoethylamine 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 463-79-6 carbonic-acid 
• 7732-18-5 water 
• 33046-24-1 tri-N-methyl-3-nitro-anilinium; bromide 
• 585-79-5 m-nitrobromobenzene 
• 506-59-2 N,N-dimethylammonium chloride 
• 67-56-1 methanol 
• 99-09-2 3-nitro-aniline 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 607-59-0 naphthalene-1-azo-(4'-dimethylaminobenzene) 
• 18600-50-5 N-methyl-N-nitroso-3-nitrobenzenamine 
• 27389-55-5 N,N,N-trimethyl-3-nitroanilinium iodide 
• 35998-95-9 N,N-dimethyl-3,4-dinitroaniline 
• 61149-61-9 N,N-dimethyl-2,5-dinitro-aniline 
• 7474-95-5 N'-acetyl-N,N-dimethyl-m-phenylenediamine 
• 27905-38-0 3-Benzamido-N,N-dimethyl-anilin 
• 55911-12-1 3-Propionylamido-N,N-dimethyl-anilin 
• 107828-87-5 N-[2-(2,6-Dibromo-4-nitro-phenylazo)-5-dimethylamino-phenyl]-acetamide 
• 25717-56-0 N-[2-(2,6-Dicyano-4-nitro-phenylazo)-5-dimethylamino-phenyl]-acetamide 
• 107828-93-3 N-[2-(2,6-Dicyano-4-nitro-phenylazo)-5-dimethylamino-phenyl]-propionamide 
• 81559-32-2 N-[2-(2-Bromo-4,6-dinitro-phenylazo)-5-dimethylamino-phenyl]-acetamide 
• 80988-33-6 N-[2-(2-Bromo-4,6-dinitro-phenylazo)-5-dimethylamino-phenyl]-propionamide 
• 15935-40-7 N-[2-(2-Cyano-4,6-dinitro-phenylazo)-5-dimethylamino-phenyl]-acetamide 

Relevant articles and documents

Detailing the elementary stages in the oxirane ring opening reactions with carboxylic acids catalyzed by tertiary amines

The study of the reaction systems “R3N – proton-donor reagent (NuH) – epichlorohydrin” using a complex of various kinetic methods of investigation allowed the reaction pathway and the catalysis mechanism of the oxirane ring opening by proton-donor reagents in the presence of R3N to be detailed. It was confirmed that the catalytic activity of R3N consists in their quaternization by oxirane under the obligatory condition of its electrophilic assistance with the NuH reagent. The quaternization process of tertiary amines was studied using 1H NMR and UV spectroscopy, quantum chemical modeling, and correlation analysis. It was shown that the transition states of the quaternization stage are dissociative, and their degree of looseness depends on the electrophilic activation of the oxirane ring.

Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides

A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.

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.