1-(Dichloromethyl)-2-nitrobenzene

Base Information

• Chemical Name: 1-(Dichloromethyl)-2-nitrobenzene
• CAS No.: 3284-77-3
• Molecular Formula: C7H5 Cl2 N O2
• Molecular Weight: 206.028
• Hs Code.: 2904909090
• European Community (EC) Number: 221-931-0
• DSSTox Substance ID: DTXSID70186507
• Nikkaji Number: J7.711I
• Wikidata: Q83057812
• Mol file: 3284-77-3.mol

Synonyms:1-(Dichloromethyl)-2-nitrobenzene;3284-77-3;EINECS 221-931-0;2-Nitro-benzalchlorid;o-Nitrobenzylidene chloride;SCHEMBL7616610;DTXSID70186507;1-(dichloro-methyl)-2-nitro-benzene

Chemical Property of 1-(Dichloromethyl)-2-nitrobenzene

Chemical Property:

• Vapor Pressure: 0.000547mmHg at 25°C
• Melting Point: 27-27.5 °C(Solv: ethanol (64-17-5))
• Boiling Point: 321.8°Cat760mmHg
• Flash Point: 148.4°C
• PSA: 45.82000
• Density: 1.46g/cm³
• LogP: 3.59420
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 204.9697338
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1-(Dichloromethyl)-2-nitrobenzene

There total 12 articles about 1-(Dichloromethyl)-2-nitrobenzene 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: 73.0%

dichloromethane (75-09-2) + 1,2-Dinitrobenzene (528-29-0) → 1-(dichloromethyl)-2-nitrobenzene (3284-77-3)

Guidance literature:

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

1,2-Dinitrobenzene; In tetrahydrofuran; hexane; at -100 ℃; for 0.00833333h; Inert atmosphere;

With trifluorormethanesulfonic acid; In tetrahydrofuran; hexane; water; at -100 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01676

Reference yield: 60.0%

2-nitro-benzaldehyde (552-89-6) → 1-(dichloromethyl)-2-nitrobenzene (3284-77-3)

Guidance literature:

With N-chloro-succinimide; chloro-diphenylphosphine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1080/00397910802271271

Reference yield: 52.0%

chloroform (67-66-3,8013-54-5) + nitrobenzene (98-95-3,26969-40-4) → 1-dichloromethyl-4-nitrobenzene (619-78-3) + 1-(dichloromethyl)-2-nitrobenzene (3284-77-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at -73 - -68 ℃; for 0.0166667h;

DOI:10.1021/jo00282a025

upstream raw materials:

chloroform

nitrobenzene

2-nitrobenzaldehyde oxime

2-nitro-benzaldehyde

Downstream raw materials:

hydrogenchloride

2-nitro-benzaldehyde

2,2'-dinitrostilbene

1-(1-Chloro-2-methyl-2-nitro-propyl)-2-nitro-benzene

Refernces

• 1、 Khutorianskyi, Viktor V.,Klepetá?ová, Blanka,Beier. "Vicarious Nucleophilic Chloromethylation of Nitroaromatics". supporting information. p. 5443 - 5446. Retrieved 2019/07/03.
• 2、 Aghapour, Ghasem,Afzali, Asieh. "Facile conversion of aldehydes and ketones to gem-dichlorides using chlorodiphenylphosphine/N-chlorosuccinimide as a new and neutral system". experimental part. p. 4023 - 4035. Retrieved 2009/04/11.