102714-71-6

Basic information

• Product Name: 4,5-DIMETHOXY-2-NITROBENZONITRILE
• Synonyms: 4,5-DIMETHOXY-2-NITROBENZONITRILE;6-NITROVERATRONITRILE;AKOS BBS-00002618;1-CYANO-4,5-DIMETHOXY-2-NITROBENZENE;Dimethoxy-2-nitrobenzonitrile;4,5-Dimethoxy-2-nitrobenzonitrile 98%;4,5-Dimethoxy-2-nitrobenzonitrile98%;1-Cyano-4,5-dimethoxy-2-nitrobenzene 6-Nitroveratronitrile
• CAS NO: 102714-71-6
• Molecular Formula: C₉H₈N₂O₄
• Molecular Weight: 208.17
• Product Categories: Aromatic Nitriles;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 102714-71-6.mol

Chemical Properties

• Melting Point: 164-168 °C(lit.)
• Boiling Point: 398.6 °C at 760 mmHg
• Flash Point: 194.9 °C
• Appearance: white to light yellow crystal powder
• Density: 1.32 g/cm³
• Vapor Pressure: 1.46E-06mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4,5-DIMETHOXY-2-NITROBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIMETHOXY-2-NITROBENZONITRILE(102714-71-6)
• EPA Substance Registry System: 4,5-DIMETHOXY-2-NITROBENZONITRILE(102714-71-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 3439 6.1/PG III
• WGK Germany: 3
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• PackingGroup: III
• Hazardous Substances Data: 102714-71-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C9H8N2O4/c1-14-8-3-6(5-10)7(11(12)13)4-9(8)15-2/h3-4H,1-2H3

Upstream product

• 4959-60-8 4,5-dimethoxy-2-nitrobenzamide 
• 2024-83-1 veratronitrile 
• 7697-37-2 nitric acid 
• 29568-78-3 4,5-dimethoxy-2-nitrobenzoyl chloride 
• 13472-08-7 azobis(2-cyanobutane) 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 109-77-3 malononitrile 
• 29577-51-3 2-nitro-4,5-dimethoxybenzaldehyde oxime 
• 4421-08-3 3-methoxy-4-hydroxybenzonitrile 

Downstream Products

• 26961-27-3 2-amino-4,5-dimethoxybenzonitrile 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 
• 849675-81-6 5-(4,5-dimethoxy-2-nitro-phenyl)-2H-tetrazole 
• 675126-26-8 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile 
• 675126-27-9 2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile 
• 184475-35-2 gefitinib 
• 228118-56-7 2-(4-chlorophenyl)-6,7-dimethoxyquinazolin-4(3H)-one 
• 371945-74-3 6,7-dimethoxy-2-phenylquinazolin-4(3Η)-one 
• 857534-65-7 2-(4-chloro-benzoylamino)-4,5-dimethoxy-benzonitrile 

Relevant articles and documents

Ag/Cu-mediated decarboxylative cyanation of aryl carboxylic acids with K4Fe(CN)6 under aerobic conditions

A method for facile synthesis of aryl nitriles has been well established via Ag/Cu-mediated decarboxylative cyanation of benzoic acids with K4Fe(CN)6 under aerobic conditions. The approach of using readily accessible aryl carboxylic acids and green K4Fe(CN)6 as starting material provides a feasible alternative to previous cyanation protocols. Control experiments revealed the key role of Cu for the process and excluded the possibility of a radical mechanism for the transformation.

Design and synthesis of 6,7-dimethoxyquinazoline analogs as multi-targeted ligands for α1- and AII-receptors antagonism

Multiple-targeted ligands can have certain advantages for the management of hypertension which has multiple controls. Molecules with dual bioactivities are available in literature for treating metabolic disorders like diabetes, hypertension and hypercholesterolemia. After scrutinizing the SAR of prazosin-type α1-blockers and AII-antagonists it was planned to develop dual α1- and AII-antagonists. Five series of quinazoline derivatives were synthesized and evaluated as dual α1- and AII-antagonists on rat aortic strips for the blockade of known α1- and AII-agonist mediated contractions. Many compounds showed balanced activity on both the receptors but compound (22) was found to be the most active derivative having higher antagonistic activity on both the receptors. In the in vivo experiments the chosen compound (22) was slightly less active than prazosin but was found to be equipotent to losartan. These findings shed a new light on the structural requirements for both α1- as well as AII-receptor antagonists.

Conversions of aryl carboxylic acids into aryl nitriles using multiple types of Cu-mediated decarboxylative cyanation under aerobic conditions

Here, we used malononitrile or AMBN as a cyanating agent to develop efficient and practical protocols for Cu-mediated decarboxylative cyanations, under aerobic conditions, of aryl carboxylic acids bearing nitro and methoxyl substituents at the ortho position as well as of heteroaromatic carboxylic acids. These protocols involved economical methods to synthesize value-added aryl nitriles from simple and inexpensive raw materials. Further diversification of the 2-nitrobenzonitrile product was performed to highlight the practicality of the protocols. This journal is

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.

Method for synthesizing aryl cyanide by taking aryl carboxylic acid as raw material

The invention discloses a method for synthesizing aryl cyanide by taking aryl carboxylic acid as a raw material, which is characterized in that aryl cyanide is synthesized by taking aryl carboxylic acid as a raw material, taking a combination of NH4X and N, N-dimethylformamide as a cyanide source and taking silver sulfate and copper acetate as catalysts under the action of acid and oxygen. Compared with a conventional aryl cyanide synthesis method, the method disclosed by the invention has the advantages that reaction raw materials (aryl carboxylic acid, NH4X and N, N-dimethylformamide) are cheap and easy to obtain, and the dosage of a metal catalyst is small; meanwhile, oxygen is used as an oxidizing agent, so that the method has the obvious advantages of small environmental pollution, good tolerance to various functional groups on an aromatic ring, high yield and the like; the method disclosed by the invention can be widely applied to synthesis of medicines, functional materials, natural products and other fields in the industry and academic circles.

Thiocyanate radical mediated dehydration of aldoximes with visible light and air

We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.

Identification of 2,4-diamino-6,7-dimethoxyquinoline derivatives as G9a inhibitors

G9a is a histone lysine methyltransferase (HKMT) involved in epigenetic regulation via the installation of histone methylation marks. 6,7-Dimethoxyquinazoline analogues, such as BIX-01294, are established as potent, substrate competitive inhibitors of G9a. With an objective to identify novel chemotypes for substrate competitive inhibitors of G9a, we have designed and synthesised a range of heterocyclic scaffolds, and investigated their ability to inhibit G9a. These studies have led to improved understanding of the key pharmacophoric features of BIX-01294 and the identification of a new core quinoline inhibitory scaffold, which retains excellent potency and high selectivity. Molecular docking was carried out to explain the observed in vitro data. This journal is

One-pot conversion of 2-nitrobenzonitriles to quinazolin-4(3H)-ones and synthesis of gefitinib and erlotinib hydrochloride

A simple and efficient one-pot conversion of 2-nitrobenzonitriles to quinazolin-4(3H)-ones involving reduction, formylation, hydrolysis and cyclization is reported. These quinazolinones have been used for making in economical way the anticancer drug molecules gefitinib (Iressa) and erlotinib HCl (Tarceva).

2-substituted methyl-2,3-dihydroimidazo[1,2-c]quinazolin-5(6H)-ones (thiones), the preparation and use thereof

The present invention provides a novel series of 2-substituted methyl-2,3-dihydroimidazo[1,2-c]quinazolin-5(6H)-ones (-thiones) compounds. These compounds are found useful as an active ingredient for the prophylaxis and treatment of hypertension.