19019-04-6

Basic information

• Product Name: 2-methoxy-3,5-dinitrobenzonitrile
• Synonyms: 2-methoxy-3,5-dinitrobenzonitrile;2-Cyano-4,6-dinitroanisole;Einecs 242-757-1
• CAS NO: 19019-04-6
• Molecular Formula: C₈H₅N₃O₅
• Molecular Weight: 223.1424
• EINECS: 242-757-1
• Mol File: 19019-04-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 388.3°Cat760mmHg
• Flash Point: 188.6°C
• Appearance: /
• Density: 1.52g/cm³
• Vapor Pressure: 3.1E-06mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 2-methoxy-3,5-dinitrobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methoxy-3,5-dinitrobenzonitrile(19019-04-6)
• EPA Substance Registry System: 2-methoxy-3,5-dinitrobenzonitrile(19019-04-6)

Safety Data

• Hazardous Substances Data: 19019-04-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H5N3O5/c1-16-8-5(4-9)2-6(10(12)13)3-7(8)11(14)15/h2-3H,1H3

Upstream product

• 10496-75-0 2-methoxy-5-nitrobenzylnitrile 
• 4110-35-4 3,5-dinitrobenzonitrile 
• 865-33-8 potassium methanolate 
• 13435-20-6 tetraethylammoniumcyanide 
• 606-35-9 1-methoxy-2,4,6-trinitrobenzene 
• 6609-56-9 2-methoxy-benzonitrile 
• 873-32-5 2-Chlorobenzonitrile 

Downstream Products

• 22603-53-8 1-amino-2-cyano-4,6-dinitrobenzene 
• 29273-56-1 2-methylamino-3,5-dinitro-benzonitrile 

Relevant articles and documents

Synthesis process of 2-amino-3,5-dinitrobenzonitrile

The invention provides a synthesis process of 2-amino-3,5-dinitrobenzonitrile. The process comprises the following steps that S1, chlorobenzonitrile and sodium methoxide are dissolved in a specific solvent, a reaction is carried out in an autoclave, after the reaction is completed, the temperature is reduced to the room temperature, an acid is used for neutralizing the mixture to be neutral, and asolvent and a first intermediate 2-methoxybenzonitrile are separated from a reaction filter liquor through rectification; S2, the first intermediate 2-methoxybenzonitrile is dissolved in the solventfor a nitration reaction, the reaction endpoint is monitored through HPLC, after the reaction is completed, elutriation operation is carried out, filtration is carried out to obtain a second intermediate 2-methoxy-3,5-dinitrobenzonitrile, and a solvent and remaining 2-methoxy-3,5-dinitrobenzonitrile are separated from the filter liquor through steam distillation; S3, the second intermediate 2-methoxy-3,5-dinitrobenzonitrile is dispersed in an ammoniation solvent, the mixture is transferred into the autoclave, a certain amount of liquid ammonia is introduced for an ammoniation reaction, and after the reaction is completed, filtration is carried out to obtain the product 2-amino-3,5-dinitrobenzonitrile.

Direct methoxylation of nitroarenes and nitroazaarenes with alkaline methoxides via nucleophilic displacement of an aromatic hydrogen atom

Treatment of 1,3-dinitrobenzene and 5-substituted derivatives with excess potassium or sodium methoxide in 1,3-dimethylimidazolidin-2-one (DMI) at room temperature results in the displacement of an aromatic hydrogen at the 4-position by methoxide, affording 2,4-dinitroanisole and its 6-substituted derivatives, respectively, in low to moderate yield. In contrast, an equimolar reaction under similar conditions leads to the replacement of the nitro group in preference to the ring hydrogen. The reaction does not take place with lithium methoxide as a base. Mono- and dinitronaphthalenes and nitroquinolines undergo similar displacement of a hydrogen atom at the position ortho or para to the nitro group, giving the corresponding methoxy derivatives in moderate yield. A slow addition of the nitro compound to a large excess of potassium methoxide under an oxygen atmosphere has been found to enhance the conversion and improve the product yield. On the basis of the product distribution as well as the kinetic isotope effect kH/kD = 2.1, direct displacement of a ring hydrogen atom by methoxide ion has been interpreted in terms of the rate-determining release of an ipso-hydrogen atom as a proton from the initially formed Meisenheimer adduct.