14227-14-6

Basic information

• Product Name: 2,4,5-Trimethoxynitrobenzene
• Synonyms: 1,2,4-Trimethoxy-5-nitrobenzene;2,4,5-Trimethoxynitrobenzene
• CAS NO: 14227-14-6
• Molecular Formula: C₉H₁₁NO₅
• Molecular Weight: 213.19
• Mol File: 14227-14-6.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 357.3 °C at 760 mmHg
• Flash Point: 169.9 °C
• Appearance: /
• Density: 1.23 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,4,5-Trimethoxynitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-Trimethoxynitrobenzene(14227-14-6)
• EPA Substance Registry System: 2,4,5-Trimethoxynitrobenzene(14227-14-6)

Safety Data

• Hazardous Substances Data: 14227-14-6(Hazardous Substances Data)

Usage

Uses

1,2,4-Trimethoxy-5-nitrobenzene is used in the synthesis of streptonigrone via one-step construction of substituted pyridones and Conrad-Limpach reaction.

Upstream product

• 7158-91-0 4,5-Dimethoxy-2-nitro-phenol 
• 77-78-1 dimethyl sulfate 
• 1818-28-6 2',4',5'-trimethoxyacetophenone 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 60-29-7 diethyl ether 
• 2883-98-9 α-asarone 
• 7664-93-9 sulfuric acid 
• 5273-86-9 C₁₂H₁₆O₃ 
• 20129-11-7 1-bromo-2,4,5-trimethoxybenzene 
• 67-56-1 methanol 
• 6940-53-0 4-chloro-2,5-dimethoxy nitrobenzene 
• 3899-65-8 1-chloro-4,5-dimethoxy-2-nitrobenzene 
• 74-88-4 methyl iodide 

Downstream Products

• 246862-42-0 6-methoxy-2-phenylquinoline-5,8-dione 
• 42065-10-1 2-chloro-5,6,8-trimethoxyquinoline 
• 1335227-01-4 (E)-3-ethoxy-N-(2,4,5-trimethoxyphenyl)acrylamide 
• 26510-91-8 2,4,5-trimethoxyaniline 

Relevant articles and documents

REACTION OF TETRANITRODIBENZO-18-CROWN-6 WITH SODIUM ALKOXIDES

It is shown that the reaction of tetranitrodibenzo-18-crown-6 with sodium alkoxides in aprotic solvents at room temperature occurs with initial cleavage of the macroheterocycle and formation of an intermediate - substituted o-dinitrobenzene - whereas the

Nitrodecarboxylation and nitrodeformylation of some electron-rich benzoic acids and benzaldehydes

The nitration ipso to a carboxylic or formyl group of disubstituted and trisubstituted benzoic acids and benzaldehydes using nitric acid in acetic acid is described.

Metal-free Transformations of Nitrogen-Oxyanions to Ammonia via Oxoammonium Salt

Transformations of nitrogen-oxyanions (NOx?) to ammonia impart pivotal roles in sustainable biogeochemical processes. While metal-mediated reductions of NOx? are relatively well known, this report illustrates proton-assisted transformations of NOx? anions in the presence of electron-rich aromatics such as 1,3,5-trimethoxybenzene (TMB?H, 1 a) leading to the formation of diaryl oxoammonium salt [(TMB)2N+=O][NO3?] (2 a) via the intermediacy of nitrosonium cation (NO+). Detailed characterizations including UV/Vis, multinuclear NMR, FT-IR, HRMS, X-ray analyses on a set of closely related metastable diaryl oxoammonium [Ar2N+=O] species disclose unambiguous structural and spectroscopic signatures. Oxoammonium salt 2 a exhibits 2 e? oxidative reactivity in the presence of oxidizable substrates such as benzylamine, thiol, and ferrocene. Intriguingly, reaction of 2 a with water affords ammonia. Perhaps of broader significance, this work reveals a new metal-free route germane to the conversion of NOx to NH3.

Electrochemical Nitration with Nitrite

Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu4NO2, which serves a dual role as supporting electrolyte and as a safe, readily available, and easy-to-handle nitro source. Stoichiometric amounts of 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP) in MeCN significantly increase the yield by solvent control. The reaction mechanism is based on electrochemical oxidation of nitrite to NO2, which initiates the nitration reaction in a divided electrolysis cell with inexpensive graphite electrodes. Overall, the reaction is demonstrated for 20 examples with yields of up to 88 %. Scalability is demonstrated by a 13-fold scale-up.

3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.