38487-85-3

Basic information

• Product Name: 2-Amino-4-methoxybenzonitrile
• Synonyms: 2-Amino-4-methoxybenzonitrile
• CAS NO: 38487-85-3
• Molecular Formula: C₈H₈N₂O
• Molecular Weight: 148.16192
• Mol File: 38487-85-3.mol

Chemical Properties

• Melting Point: 96 °C
• Boiling Point: 341.5 °C at 760 mmHg
• Flash Point: 160.4 °C
• Appearance: /
• Density: 1.17 g/cm³
• Vapor Pressure: 8E-05mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.39±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-4-methoxybenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-methoxybenzonitrile(38487-85-3)
• EPA Substance Registry System: 2-Amino-4-methoxybenzonitrile(38487-85-3)

Safety Data

• Hazardous Substances Data: 38487-85-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-methoxybenzonitrile is used as a building block in organic synthesis for the preparation of various pharmaceuticals. Its unique structure contributes to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Amino-4-methoxybenzonitrile serves as a key intermediate in the synthesis of agrochemicals, aiding in the creation of compounds that can protect crops from pests and diseases.
Used in Dye Industry:
2-Amino-4-methoxybenzonitrile is utilized in the production of dyes, where its aromatic structure and functional groups enable the creation of a wide range of colorants for various applications.
Used in Organic Electronic Materials:
2-Amino-4-methoxybenzonitrile is also employed in the development of organic electronic materials, such as organic light-emitting diodes (OLEDs) and organic solar cells, due to its electronic properties and potential for molecular engineering.
Used in Medicinal Research:
2-Amino-4-methoxybenzonitrile is used as a subject of investigation in medicinal research for its potential anti-cancer and anti-inflammatory activities, with the aim of discovering new therapeutic agents for various diseases.

InChI:InChI=1/C8H8N2O/c1-11-7-3-2-6(5-9)8(10)4-7/h2-4H,10H2,1H3

Upstream product

• 38469-83-9 4-methoxy-2-nitro-benzonitrile 
• 874-90-8 4-methoxybenzonitrile 
• 1210035-07-6 2-(cyanothioformamido)-4-methoxybenzonitrile 
• 603-35-0 triphenylphosphine 
• 1192690-78-0 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-4-methoxybenzonitrile 
• 96-96-8 4-methoxy-2-nitroaniline 
• 110-86-1 pyridine 
• 109128-43-0 6'-methoxy-spiro[cyclopentane-1,2'-indolin]-3'-one oxime 
• 7732-18-5 water 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 939970-64-6 O-ethyl ester of 2-cyano-5-methoxyphenyl dithiocarbonic acid 
• 490039-83-3 2-iodo-4-methoxybenzonitrile 
• 855877-33-7 2-[(N-acetyl-sulfanilyl)-amino]-4-methoxy-benzonitrile 
• 855275-45-5 2-(4-chloro-benzoylamino)-4-methoxy-benzonitrile 
• 103040-84-2 N-(2-cyano-5-methoxyphenyl)acetamide 
• 62484-12-2 7-methoxyquinazoline-2,4(1H,3H)-dione 
• 42465-53-2 1-(2-amino-4-methoxyphenyl)ethanone 
• 90347-63-0 1-(2-iodo-4-methoxyphenyl)ethanone 

Relevant articles and documents

Substrate-Independent High-Throughput Assay for the Quantification of Aldehydes

The selective and direct reduction of carboxylic acids into the corresponding aldehydes by chemical methods is still a challenging task in synthesis. Several reductive and oxidative chemical methods are known to produce aldehydes, but most of them require

Pyridyl Radical Cation for C?H Amination of Arenes

Electron-transfer photocatalysis provides access to the elusive and unprecedented N-pyridyl radical cation from selected N-substituted pyridinium reagents. The resulting C(sp2)?H functionalization of (hetero)arenes furnishes versatile intermediates for the development of valuable aminated aryl scaffolds. Mechanistic studies that include the first spectroscopic evidence of a spin-trapped N-pyridyl radical adduct implicate SET-triggered, pseudo-mesolytic cleavage of the N?X pyridinium reagents mediated by visible light.

The conversion of 2-cyano cyanothioformanilides into 3-aminoindole-2- carbonitriles using triphenylphosphine

2-Cyano cyanothioformanilide 3a reacts with triphenylphosphine in the presence of water to give 2-(cyanomethyleneamino)benzonitrile 4a, 2-(cyanomethylamino)benzonitrile 5, 3-aminoindole-2-carbonitrile 2a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 6a. In the presence of p-toluenesulfonic acid in MeOH the reaction between 2-cyano cyanothioformanilide 3a and triphenylphosphine (2 equiv) gives 3-aminoindole-2-carbonitrile 2a in 90% yield. Under the same conditions 2-(cyanomethyleneamino)benzonitrile 4a gives anthranilonitrile 8a, 3-aminoindole-2-carbonitrile 2a and N-(2-cyanophenyl)formamide 9. In addition, substituted 2-cyano cyanothioformanilides 3b-f react with triphenylphosphine and p-toluenesulfonic acid in MeOH to give 3-aminoindole-2-carbonitriles 2b-f in 63-75% yields. Under analogous conditions 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 2g gives only 4,5-dimethoxyanthranilonitrile 8g and 4,6,7-trimethoxyquinazoline-2- carbonitrile 14g, but in refluxing dry PhMe in the absence of p-toluenesulfonic acid 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 3g, (2-cyano-5,6- dimethoxyindol-3-yl)iminotriphenylphosphorane 6g and 2-(cyanomethyleneamino)-4, 5-dimethoxybenzonitrile 4g are obtained. The structure of 2- (cyanomethyleneamino)-4,5-dimethoxybenzonitrile 4g is supported unambiguously via independent synthesis and comparison to the isomeric 6,7- dimethoxyquinazoline-2-carbonitrile 15. All new compounds are fully characterised and a tentative mechanism for the transformation of 2-cyano cyanothioformanilides to indoles is proposed.

Therapeutic Compounds and Their Use in Treating Diseases and Disorders

The invention provides novel therapeutic compounds, pharmaceutical compositions comprising these compounds, and methods for using these compounds and compositions to treat diseases and disorders, such as cancer.

The conversion of 2-(4-chloro-5H-1,2,3-dithiazolylideneamino)benzonitriles into 3-aminoindole-2-carbonitriles using triphenylphosphine

2-(4-Chloro-5H-1,2,3-dithiazolylideneamino)benzonitrile 1a reacts with triphenylphosphine (4 equiv) in the presence of water (2 equiv) to afford anthranilonitrile 2a, 3-aminoindole-2-carbonitrile 3a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 4a, tog

Carbopalladation of nitriles: Synthesis of 2,3-diarylindenones and polycyclic aromatic ketones by the Pd-catalyzed annulation of alkynes and bicyclic alkenes by 2-iodoarenenitriles

2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(O)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon-nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.