n-(2-Chloroethyl)-4-nitrobenzamide

Base Information

• Chemical Name: n-(2-Chloroethyl)-4-nitrobenzamide
• CAS No.: 51816-15-0
• Molecular Formula: C9H9 Cl N2 O3
• Molecular Weight: 228.635
• Hs Code.: 2924299090
• NSC Number: 49011
• DSSTox Substance ID: DTXSID20287119
• Wikidata: Q82023045
• Mol file: 51816-15-0.mol

Synonyms:n-(2-chloroethyl)-4-nitrobenzamide;51816-15-0;N-(2-CHLOROETHYL)-4-NITRO-BENZAMIDE;NSC49011;SCHEMBL5610870;DTXSID20287119;ZSSIFUDFKRJWMF-UHFFFAOYSA-N;NSC-49011;AKOS010539142;CS-0264045;EN300-9157555

Chemical Property of n-(2-Chloroethyl)-4-nitrobenzamide

Chemical Property:

• Vapor Pressure: 9.62E-08mmHg at 25°C
• Boiling Point: 434.2°Cat760mmHg
• PKA: 12.54±0.46(Predicted)
• Flash Point: 216.4°C
• PSA: 74.92000
• Density: 1.348g/cm³
• LogP: 2.47750
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 228.0301698
• Heavy Atom Count: 15
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of n-(2-Chloroethyl)-4-nitrobenzamide

There total 6 articles about n-(2-Chloroethyl)-4-nitrobenzamide 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: 48.0%

4-nitrobenzyl chloride (619-73-8) + 2-chloroethanamine hydrochloride (870-24-6) → N-(2-chloroethyl)-4-nitrobenzamide (51816-15-0)

Guidance literature:

With tert.-butylhydroperoxide; tris(bipyridine)ruthenium(II) dichloride hexahydrate; calcium carbonate; In water; ethyl acetate; at 20 ℃; for 72h; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.0c01320

Reference yield:

1-chlorocarbonyloxy-2-(4-nitro-benzoylamino)-ethane (99183-81-0) → N-(2-chloroethyl)-4-nitrobenzamide (51816-15-0)

Guidance literature:

With 1,4-dioxane;

DOI:10.1021/ja01600a042

Reference yield:

2-chloroethanamine hydrochloride (870-24-6) + 4-nitro-benzoic acid (62-23-7) → N-(2-chloroethyl)-4-nitrobenzamide (51816-15-0)

Guidance literature:

4-nitro-benzoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

2-chloroethanamine hydrochloride; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.3998/ark.5550190.p009.609

upstream raw materials:

pyridine

2-chloroethanamine hydrochloride

4-nitro-benzoyl chloride

1-chlorocarbonyloxy-2-(4-nitro-benzoylamino)-ethane

Downstream raw materials:

1-(4-methoxyphenyl)-2-(4-nitrophenyl)-4,5-dihydroimidazole

C₁₅H₂₇N₆O₃P

2-(4-nitrophenyl)-4,5-dihydro-1H-imidazoline

N-(2-Azidoethyl)p-nitrobenzamid

Refernces

• 1、 Gutierrez, David A.,Dean, Dayton R.,Laxamana, Candace M.,Migliozzi-Smith, Madyson,O'Brien, Connor J.,O'Neill, Claire L.,Li, Jie Jack. "Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles". . p. 261 - 276. Retrieved 2016/07/06.