4-(Chloromethyl)-3-nitrobenzonitrile

Base Information

• Chemical Name: 4-(Chloromethyl)-3-nitrobenzonitrile
• CAS No.: 90178-80-6
• Molecular Formula: C8H5ClN2O2
• Molecular Weight: 196.593
• DSSTox Substance ID: DTXSID30531094
• Wikidata: Q82402685
• Mol file: 90178-80-6.mol

Synonyms:4-(Chloromethyl)-3-nitrobenzonitrile;90178-80-6;Benzonitrile, 4-(chloromethyl)-3-nitro-;DTXSID30531094

Chemical Property of 4-(Chloromethyl)-3-nitrobenzonitrile

Chemical Property:

• PSA: 69.61000
• LogP: 2.72848
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 196.0039551
• Heavy Atom Count: 13
• Complexity: 242

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C#N)[N+](=O)[O-])CCl

Technology Process of 4-(Chloromethyl)-3-nitrobenzonitrile

There total 1 articles about 4-(Chloromethyl)-3-nitrobenzonitrile 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: 88.0%

dichloromethane (75-09-2) + 3-nitrobenzonitrile (619-24-9) → 4-(chloromethyl)-3-nitrobenzonitrile (90178-80-6)

Guidance literature:

dichloromethane; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.333333h; Inert atmosphere;

3-nitrobenzonitrile; With N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -100 ℃; for 6h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; hexane; water; at -100 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01676

Reference yield: 96.0%

pyridine (110-86-1) + 4-(chloromethyl)-3-nitrobenzonitrile (90178-80-6) → 1-(4-Cyan-2-nitrobenzyl)pyridiniumchlorid (90179-04-7)

Guidance literature:

With potassium hydroxide; for 0.25h; Heating;

DOI:10.1002/jlac.198419840302

Reference yield: 76.0%

4-(chloromethyl)-3-nitrobenzonitrile (90178-80-6) → 4-Cyan-2-nitrobenzyliodid (90178-76-0)

Guidance literature:

With sodium iodide; In acetone; for 6h;

DOI:10.1002/jlac.198419840302

upstream raw materials:

dichloromethane

3-nitrobenzonitrile

Downstream raw materials:

Ethyl 4-(chloromethyl)-3-nitrobenzoate

5-cyano-2-methylaniline

1-(4-Cyan-2-nitrobenzyl)pyridiniumchlorid

4-Cyan-2-nitrobenzyliodid

Refernces