1527-89-5

Basic information

• Product Name: 3-Methoxybenzonitrile
• Synonyms: 1-Cyano-3-methoxybenzene;1-Methoxy-3-cyanobenzene;3-Methoxybenzonitrile,98%;3-Methoxybenzonitrile, 98% 5ML;3-Cyanoanisole, m-Anisonitrile;3-Methoxybenzonitrile, 97+%;Between Methoxy benzene nitrile;M-ANISONITRILE
• CAS NO: 1527-89-5
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.15
• EINECS: 216-201-3
• Product Categories: Phenyls & Phenyl-Het;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;cyanide;Aromatic Nitriles;Phenyls & Phenyl-Het;Nitriles
• Mol File: 1527-89-5.mol
• Article Data: 171

Chemical Properties

• Melting Point: 20-22°C
• Boiling Point: 111-112 °C13 mm Hg(lit.)
• Flash Point: 221 °F
• Appearance: clear colourless to light yellow liquid
• Density: 1.089 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0567mmHg at 25°C
• Refractive Index: n20/D 1.5402(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Slightly soluble in water
• BRN: 1932666
• CAS DataBase Reference: 3-Methoxybenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxybenzonitrile(1527-89-5)
• EPA Substance Registry System: 3-Methoxybenzonitrile(1527-89-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36/37-24/25
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1527-89-5(Hazardous Substances Data)

Usage

Description

3-Methoxybenzonitrile, also known as m-anisatonitrile, is an organic compound with the chemical formula C8H7NO. It is a clear colorless to light yellow liquid that undergoes dealkylation when treated with SiCl4/LiI and BF3. 3-Methoxybenzonitrile is known for its versatile chemical properties and applications in various industries.

Uses

Used in Chemical Synthesis:
3-Methoxybenzonitrile is used as a key intermediate in the synthesis of various organic compounds, particularly in the production of pharmaceuticals and agrochemicals. Its unique chemical structure allows for further functionalization and modification, making it a valuable building block in the development of new molecules with specific properties and applications.
Used in Organic Pigment Synthesis:
3-Methoxybenzonitrile is used as a starting material for the synthesis of new organic pigments. These pigments have been evaluated as the active medium of solid-state dye lasers, showcasing the compound's importance in the development of advanced laser technologies.
Used in the Pharmaceutical Industry:
In the pharmaceutical industry, 3-Methoxybenzonitrile is utilized as a precursor for the synthesis of various active pharmaceutical ingredients (APIs). Its unique chemical properties enable the creation of novel drug candidates with potential therapeutic applications.
Used in the Agrochemical Industry:
3-Methoxybenzonitrile is also employed in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its versatility in chemical reactions allows for the development of innovative products that can help improve crop yields and protect against various pests and diseases.

InChI:InChI=1/C8H7NO/c1-10-8-4-2-3-7(5-8)6-9/h2-5H,1H3

Upstream product

• 860724-68-1 chloro-(3-methoxy-benzyliden)-amine 
• 115484-88-3 1-(3-methoxy-phenyl)-nonadecan-2-one 
• 141-52-6 sodium ethanolate 
• 110-46-3 isopentyl nitrite 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 536-90-3 m-Anisidine 
• 58296-98-3 3-methoxybenzaldehyde N,N-dimethylhydrazone 
• 38489-80-4 (E)-3-methoxybenzaldoxime 
• 2398-37-0 3-methoxyphenyl bromide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 123767-44-2 3-methoxylbenzyl azide 
• 10365-98-7 3-methoxyphenylboronic acid 

Downstream Products

• 5585-14-8 3,4-diphenyl-furazan 2-oxide 
• 54494-11-0 5-(3-methoxyphenyl)-3-phenyl-1,2,4-oxadiazole 
• 10002-44-5 2-(3'-methoxyphenyl)benzothiazole 
• 186835-00-7 6-(3-Methoxy-phenyl)-[1,3,5]triazine-2,4-diamine 
• 61161-41-9 2-(3-methoxyphenyl)-4,5-dihydro-1H-imidazole 
• 348637-69-4 6-(3-methoxylphenyl)-5H-pyrrolo[2,3-b]pyrazine 
• 99209-60-6 1-(3-methoxyphenyl)-1-octyne 
• 27834-99-7 ethyl (3-methoxybenzoyl)acetate 
• 17816-49-8 5-(3-methoxy-phenyl)-5-phenyl-imidazolidine-2,4-dione 
• 491859-14-4 2-(3-methoxyphenyl)-6-(pentafluoroethyl)-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine 
• 1192469-28-5 2-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine 
• 1192469-36-5 5-(tert-butyl)-3-(3-methoxyphenyl)-1H-1,2,4-triazole 
• 1164111-45-8 C₉H₁₁NO*ClH 
• 1226772-08-2 2-(cyclohexyl-hydroxy-methyl)-3-methoxy-benzonitrile 

Relevant articles and documents

Increasing the scope of palladium-catalyzed cyanations of aryl chlorides

An improved protocol for the palladium-catalyzed cyanation of electron-rich aryl chlorides with potassium ferrocyanide [K4[Fe(CN)6]] is presented. Compared to previous procedures the substrate scope is significantly broadened.

Synthesis of low molecular weight compounds with complement inhibition activity

An attempt was made to synthesize a series of non-cytotoxic low molecular weight meta-substituted aromatic ethers (2-4, 5-7) and some of their bioisosteres (14-16) and to evaluate their activity on the activation of human complement (classical pathway) and their intrinsic hemolytic activity. The in vitro assay results of the inhibition of complement-mediated hemolysis by these analogues indicate that the aldehydic meta substituted aromatic ethers show inhibitory potency, while carboxylic acid meta substituted aromatic ethers show hemolytic activity. Some of the bioisosteres exhibit both inhibitory as well as hemolytic property.

Highly dispersed Co species in N-doped carbon enhanced the aldehydes ammoxidation reaction activity

Developing environmentally friendly catalysts with high activity for the ammoxidation of aromatic aldehydes to aromatic nitriles is greatly important for this industrial transformation. Herein, natural vitamin B12 was used as a carbon source for the preparation of a cobalt- and nitrogen-doped catalyst precursor, which was pyrolyzed at different temperatures to obtain cobalt- and nitrogen-doped carbon (Co@NC-T) (T denotes pyrolysis temperature) catalysts. The Co@NC-800 exhibited excellent activity and selectivity in the ammoxidation of aromatic aldehydes with ammonium carbonate to aromatic nitriles compared to the Co@NC-700, Co@NC-600 and Co@NC-500 catalysts. The high catalytic performance of Co@NC-800 could be due to the presence of the low-density electron cloud of the highly dispersed Co species, which could interact with the benzene ring of benzaldehyde bearing p-π conjugate, thereby promoting the adsorption and activation of benzaldehyde. Consequently, the activated benzaldehyde reacted with amino groups that were decomposed from ammonium carbonate and subsequently underwent a dehydration process to form nitriles.

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.