2-Ethoxybenzonitrile

Base Information

• Chemical Name: 2-Ethoxybenzonitrile
• CAS No.: 6609-57-0
• Molecular Formula: C9H9 N O
• Molecular Weight: 147.177
• Hs Code.: 29269095
• European Community (EC) Number: 613-895-3
• DSSTox Substance ID: DTXSID90341919
• Nikkaji Number: J410.621K
• Wikidata: Q72471307
• Mol file: 6609-57-0.mol

Synonyms:Benzonitrile,o-ethoxy- (7CI,8CI); 2-Ethoxybenzonitrile; o-Ethoxybenzonitrile

Chemical Property of 2-Ethoxybenzonitrile

Chemical Property:

• Vapor Pressure: 0.0104mmHg at 25°C
• Melting Point: 5°C(lit.)
• Refractive Index: n20/D 1.5322(lit.)
• Boiling Point: 154°C 20mm
• Flash Point: >110 ºC
• PSA: 33.02000
• Density: 1.053
• LogP: 1.95698
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

98% ^*data from raw suppliers

2-Ethoxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=CC=C1C#N
• Uses: 2-Ethoxybenzonitrile has been used in the synthesis of selective phosphodiesterase(V) inhibitor, vardenafil.

Technology Process of 2-Ethoxybenzonitrile

There total 20 articles about 2-Ethoxybenzonitrile 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: 98.0%

2-Chlorobenzonitrile (873-32-5) + ethanol (64-17-5) → 2-ethoxybenzonitrile (6609-57-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 25 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.joc.0c01250

Reference yield: 97.0%

ethyl bromide (74-96-4) + salicylonitrile (611-20-1) → 2-ethoxybenzonitrile (6609-57-0)

Guidance literature:

With potassium carbonate; In acetone; Heating / reflux;

Reference yield: 95.0%

2-ethoxybenzamide (938-73-8) → 2-ethoxybenzonitrile (6609-57-0)

Guidance literature:

2-ethoxybenzamide; With C₃₉H₄₅N₂; In acetonitrile; at 20 ℃; Schlenk technique; Glovebox; Inert atmosphere;

With phenylsilane; In acetonitrile; at 20 ℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1039/c9cc08413d

upstream raw materials:

2-ethoxy-benzaldehyde-oxime

acetic anhydride

ortho-phenitidine

ethanol

Downstream raw materials:

2-ethoxybenzamide

2-ethoxybenzoic acid

(E,E)-bis-(2-ethoxy-benzylidene)-hydrazine

2-ethoxy-3,5-dinitro-benzonitrile

Refernces

• 1、 Ando, Shin,Tsuzaki, Marina,Ishizuka, Tadao. "Aryl Ether Syntheses via Aromatic Substitution Proceeding under Mild Conditions". . p. 11181 - 11189. Retrieved 2020/10/12.
• 2、 -. "Oxadiazole pyrazole compound and application thereof". Paragraph 0021; 0022; 0023. . Retrieved 2018/09/08.