5910-19-0

Basic information

• Product Name: N-methyl-2,6-dinitroaniline
• Synonyms: N-methyl-2,6-dinitroaniline;N-Methyl-2,6-dinitrobenzenamine;Einecs 227-620-6
• CAS NO: 5910-19-0
• Molecular Formula: C₇H₇N₃O₄
• Molecular Weight: 197.14818
• EINECS: 227-620-6
• Mol File: 5910-19-0.mol

Chemical Properties

• Boiling Point: 342.4°Cat760mmHg
• Flash Point: 160.9°C
• Appearance: /
• Density: 1.487g/cm³
• Vapor Pressure: 7.54E-05mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: N-methyl-2,6-dinitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-2,6-dinitroaniline(5910-19-0)
• EPA Substance Registry System: N-methyl-2,6-dinitroaniline(5910-19-0)

Safety Data

• Hazardous Substances Data: 5910-19-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H7N3O4/c1-8-7-5(9(11)12)3-2-4-6(7)10(13)14/h2-4,8H,1H3

Upstream product

• 67-56-1 methanol 
• 606-21-3 1-chloro-2,6-dinitrobenzene 
• 74-89-5 methylamine 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 860766-46-7 N¹-methyl-2,6-dinitro-p-phenylenediamine 
• 7647-01-0 hydrogenchloride 
• 857621-25-1 acetic acid-[4-(methyl-nitroso-amino)-3,5-dinitro-anilide] 
• 102877-65-6 N-methyl-N-(2-nitrophenyl)nitramine 
• 64-19-7 acetic acid 
• 861613-61-8 acetic acid-(4-methylamino-3,5-dinitro-anilide) 
• 7463-28-7 N'-acetyl-N,N-dimethyl-1,4-phenylenediamine 
• 612-28-2 2-nitro-N-methylaniline 

Downstream Products

• 851888-60-3 1-methyl-7-[(4-methylsulfonyl)phenylamino]-1,3-dihydro-2H-benzimidazol-2-one 
• 851888-38-5 7-[(4-chlorophenyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one 
• 851887-60-0 7-[(4-methoxyphenyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one 

Relevant articles and documents

Design and Synthesis of Benzimidazoles As Novel Corticotropin-Releasing Factor 1 Receptor Antagonists

Benzazole derivatives with a flexible aryl group bonded through a one-atom linker as a new scaffold for a corticotropin-releasing factor 1 (CRF1) receptor antagonist were designed, synthesized, and evaluated. We expected that structural diversity could be expanded beyond that of reported CRF1 receptor antagonists. In a structure-activity relationship study, 4-chloro-N2-(4-chloro-2-methoxy-6-methylphenyl)-1-methyl-N7,N7-dipropyl-1H-benzimidazole-2,7-diamine 29g had the most potent binding activity against a human CRF1 receptor and the antagonistic activity (IC50 = 9.5 and 88 nM, respectively) without concerns regarding cytotoxicity at 30 μM. Potent CRF1 receptor-binding activity in brain in an ex vivo test and suppression of stress-induced activation of the hypothalamus-pituitary-adrenocortical (HPA) axis were also observed at 138 μmol/kg of compound 29g after oral administration in mice. Thus, the newly designed benzimidazole 29g showed in vivo CRF1 receptor antagonistic activity and good brain penetration, indicating that it is a promising lead for CRF1 receptor antagonist drug discovery research.

Discovery of a 7-arylaminobenzimidazole series as novel CRF1receptor antagonists

A promising lead compound 1 of a benzimidazole series has been identified as a corticotropin-releasing factor 1 (CRF1) receptor antagonist. In this study, we focused on replacement of a 7-alkylamino group of 1, predicted to occupy a large lipophilic pocket of a CRF1receptor, with an aryl group. During the course of this examination, we established new synthetic approaches to 2,7-diarylaminobenzimidazoles. The novel synthesis of 7-arylaminobenzimidazoles culminated in the identification of compounds exhibiting inhibitory activities comparable to the alkyl analog 1. A representative compound, p-methoxyanilino analog 16g, showed potent CRF binding inhibitory activity against a human CRF1receptor and human CRF1receptor antagonistic activity (IC50?=?27?nM, 56?nM, respectively). This compound exhibited ex vivo125I-Tyr0(125I-CRF) binding inhibitory activity in mouse frontal cortex, olfactory bulb, and pituitary gland at 20?mg/kg after oral administration. In this report, we discuss the structure–activity-relationship of these 7-arylamino-1H-benzimidazoles and their synthetic method.

Synthesis, properties, and molecular structure of nitro-substituted N-methyl-N-nitroanilines

Ten mono-, di-, and trinitro derivatives of N-methyl-N-nitroaniline were synthesized and studied by spectral, electrooptical, and quantum-chemical methods. Three of these derivatives, N-methyl-N,2,3-trinitroaniline, N-methyl-N,2,5-trinitroaniline, N-methyl-N,3,5-trinitroaniline, were also examined by the X-ray diffraction method. The N-nitroamino group in their molecules is almost planar, the N7-N8 bond is shortened, and the N8 atom is characterized by a strong deficit of electron density. The dihedral angle between the planes of the N-nitroamino group and the benzene ring is 56°-92°, which makes conjugation between these fragments impossible. The N-nitroamino group in the examined compounds acts as a weak electron donor with respect to the nitro groups in the aromatic ring; the mechanism of this effect is inductive. Pleiades Publishing, Inc. 2006.

NITROGEN-CONTAINING FUSED HETEROCYCLIC COMPOUNDS

There is provided a CRF receptor antagonist comprising a compound of the formula (I): wherein, ring A is a 5-membered ring represented by the formula (A'): wherein X is a carbon and X is an oxygen, a sulfur or - NR -,or formula (A"): wherein X is a nitrogen and R is an optionally substituted hydrocarbyl, Ris an amino substituted by two optionally substituted hydrocarbyl groups, Ris an phenyl, Y is CR or a nitrogen, Y is CRor a nitrogen and Yis CRor a nitrogen, provided that one or less of Y, Y, and Y is nitrogen, W is a bond, -(CH2)n-, and Z is a bond, -NR -,etc.; or a salt thereof or a prodrug thereof.

Construction of interconnected acidity functions based on ortho substituted anilines and N-methylanilines as indicators

The log I values of 15 mainly ortho substituted derivatives of aniline and N-methylaniline have been measured spectrophotometrically in sulfuric, perchloric, and methanesulfonic acids. A new algorithm has been suggested for construction of acidity functions enabling simultaneous and independent construction of acidity functions in various media under the condition of equal values of pKa of the same indicators in the given media. The so-called interconnected acidity functions have been constructed with using this algorithm and the log I values measured in the above media, and the pKa values have been calculated. The resulting acidity functions and pKa values agree well with the corresponding literature data.

Amination of dinitrobenzenes with liquid methylamine/potassium permanganate

1,3-Dinitrobenzene (1a) and some simple monosubstituted derivatives (1b-g) were aminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to give the corresponding mono- and bis(methylamino)-substituted compounds (3a-e and 4a). 1,2-Dinitrobenzene (1i) was aminated with LMA/PP to give 2-(methylamino)-1-nitrobenzene (3f) in high yield.The intermediacy of 4-(methylamino) ?-adducts of 1,3-dinitrobenzene (2a), 2-chloro- (2b) and 2-amino-1,3-dinitrobenzene (2c) was established by 1H NMR spectroscopy.Quantum-chemical calculations for the dinitrobenzenes suggest that, in general, the experimentally observed regioselectivity of the methylamination is satisfactorily described by frontier molecular orbital (FMO) interaction of the reagents.