2-Chloro-5-methoxybenzonitrile

Base Information

• Chemical Name: 2-Chloro-5-methoxybenzonitrile
• CAS No.: 127667-00-9
• Molecular Formula: C8H6ClNO
• Molecular Weight: 167.595
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID30563259
• Nikkaji Number: J336.399F
• Wikidata: Q82447647
• Mol file: 127667-00-9.mol

Synonyms:2-CHLORO-5-METHOXYBENZONITRILE;127667-00-9;Benzonitrile, 2-chloro-5-methoxy-;MFCD08061919;SCHEMBL10662281;DTXSID30563259;AMY14464;AKOS006287396;AS-33148;SY111321;CS-0099150;A21144

Chemical Property of 2-Chloro-5-methoxybenzonitrile

Chemical Property:

• Vapor Pressure: 0.0083mmHg at 25°C
• Boiling Point: 267.1°C at 760 mmHg
• Flash Point: 115.4°C
• PSA: 33.02000
• Density: 1.25g/cm³
• LogP: 2.22028
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 167.0137915
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-5-methoxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)Cl)C#N

Technology Process of 2-Chloro-5-methoxybenzonitrile

There total 6 articles about 2-Chloro-5-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: 93.0%

C9H10ClNO2 (1146731-96-5) → 2-chloro-5-methoxybenzonitrile (127667-00-9)

Guidance literature:

With [Ru(η⁶-p-cymene)Cl₂]₂; acrylic acid methyl ester; diphenyl acetylene; In isopropyl alcohol; at 100 ℃; for 16h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c3cc41124a

Reference yield:

2-chloro-5-methoxybenzaldehyde oxime → 2-chloro-5-methoxybenzonitrile (127667-00-9)

Guidance literature:

With acetic anhydride; triethylamine; In tetrahydrofuran;

Reference yield:

4-chloromethoxybenzene (623-12-1) → 2-chloro-5-methoxybenzonitrile (127667-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C

1.2: -78 - 20 °C

2.1: hydroxylamine hydrochloride / ethanol / 4 h / Reflux

3.1: acetic anhydride; triethylamine / tetrahydrofuran

With n-butyllithium; hydroxylamine hydrochloride; acetic anhydride; triethylamine; In tetrahydrofuran; ethanol;

upstream raw materials:

2-chloro-5-methoxyaniline

copper(I) cyanide

C₉H₁₀ClNO₂

4-chloromethoxybenzene

Downstream raw materials:

2-chloro-5-methoxybenzimidamide

2-(Cyano-phenyl-methyl)-5-methoxy-benzonitrile

Refernces

• 1、 Chinnagolla, Ravi Kiran,Pimparkar, Sandeep,Jeganmohan, Masilamani. "Ruthenium-catalyzed intramolecular selective halogenation of O-methylbenzohydroximoyl halides: A new route to halogenated aromatic nitriles". supporting information. p. 3146 - 3148. Retrieved 2013/06/04.