2-Methoxybenzonitrile

Base Information

• Chemical Name: 2-Methoxybenzonitrile
• CAS No.: 6609-56-9
• Molecular Formula: C8H7NO
• Molecular Weight: 133.15
• Hs Code.: 29269090
• European Community (EC) Number: 229-559-0
• DSSTox Substance ID: DTXSID10216291
• Nikkaji Number: J150.105D
• Wikidata: Q72457847
• Mol file: 6609-56-9.mol

Synonyms:2-methoxybenzonitrile;o-methoxybenzonitrile;ortho-methoxybenzonitrile

Chemical Property of 2-Methoxybenzonitrile

Chemical Property:

• Appearance/Colour: Colorless to yellow clear liquid
• Vapor Pressure: 0.0162mmHg at 25°C
• Melting Point: 24.5°C
• Refractive Index: n20/D 1.5465(lit.)
• Boiling Point: 255.5 °C at 760 mmHg
• Flash Point: 103.4 °C
• PSA: 33.02000
• Density: 1.08 g/cm³
• LogP: 1.56688
• Storage Temp.: Room temperature.
• Water Solubility.: Slightly soluble in water
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 133.052763847
• Heavy Atom Count: 10
• Complexity: 147

Purity/Quality:

98% ^*data from raw suppliers

2-Methoxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=CC=C1C#N
• Uses: 2-Methoxybenzonitrile was used in the synthesis of 5-(4′-methyl [1,1′-biphenyl]-2-yl)-1H-tetrazole.

Technology Process of 2-Methoxybenzonitrile

There total 170 articles about 2-Methoxybenzonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-methoxybenzylamine (6850-57-3) → 2-methoxy-benzonitrile (6609-56-9)

Guidance literature:

With oxygen; In acetone; at 20 ℃; for 4.6h; Electrochemical reaction;

DOI:10.1002/chem.201103913

Reference yield: 99.0%

ortho-anisaldehyde (135-02-4) → 2-methoxy-benzonitrile (6609-56-9)

Guidance literature:

With ammonium iodide; In dimethyl sulfoxide; at 20 ℃; for 4h; Electrolysis;

DOI:10.1007/s11426-015-5331-z

Reference yield: 94.0%

potassiumhexacyanoferrate(II) trihydrate + 2-Chloroanisole (766-51-8) → 2-methoxy-benzonitrile (6609-56-9)

Guidance literature:

potassiumhexacyanoferrate(II) trihydrate; 2-Chloroanisole; With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; potassium carbonate; In water; at 120 ℃; for 12h; Inert atmosphere; Sealed tube;

potassiumhexacyanoferrate(II) trihydrate; 2-Chloroanisole; With potassium carbonate; In water; at 120 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1007/s10562-021-03864-6

upstream raw materials:

tetrachloromethane

2-methoxy-benzaldehyde-((E)-O-benzoyl oxime )

diethyl ether

ethylmagnesium bromide

Downstream raw materials:

1-(2-methoxyphenyl)propan-1-one

2-Methoxyacetophenone

2-methoxy-benzophenone-imine

N,N-dibutyl-2-methoxy-benzamidine

Refernces

Deuterated Aryl Alkyl Ethers Synthesis via Nucleophilic Etherification of Aryl Alkyl Ethers and Thioethers with Deuterated Alcohols

10.1055/s-0037-1611898

The research aims to develop a practical and transition-metal-free etherification protocol for synthesizing deuterated ethers, which have significant applications in pharmaceutical discoveries and developments. The study explores the nucleophilic etherification of aryl alkyl ethers and thioethers using deuterated alcohols in the presence of potassium tert-butoxide (KOt-Bu) under mild reaction conditions. The researchers found that a wide range of sterically bulky deuterated alcohols and aryl ethers, including methoxybenzonitriles and aryl alkyl thioethers, were suitable for this transformation, achieving yields up to 97%. Mechanistic studies suggested that the reaction proceeds via a nucleophilic aromatic substitution pathway. The developed method provides a simple yet effective technique for generating deuterated ethers, which are difficult to prepare using traditional Williamson etherification, and is expected to have broad applications in the pharmaceutical field.