meso-1,2-Bis(4-chlorophenyl)ethylenediamine

Base Information

• Chemical Name: meso-1,2-Bis(4-chlorophenyl)ethylenediamine
• CAS No.: 74641-30-8
• Molecular Formula: C₁₄H₁₄Cl₂N₂
• Molecular Weight: 281.185
• Mol file: 74641-30-8.mol

Synonyms:1,2-Ethanediamine,1,2-bis(4-chlorophenyl)-, (R*,S*)-;Meso-1,2-Bis(4-chlorophenyl)ethylenediamine;meso-1,2-Bis(4-chlorophenyl)ethane-1,2-diamine;

Chemical Property of meso-1,2-Bis(4-chlorophenyl)ethylenediamine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 418.6 °C at 760 mmHg
• PKA: 9.32±0.10(Predicted)
• Flash Point: 206.9 °C
• PSA: 52.04000
• Density: 1.303 g/cm³
• LogP: 5.09380
• Storage Temp.: 2-8°C(protect from light)
• Sensitive.: air sensitive

Purity/Quality:

99%, ^*data from raw suppliers

(1R,2S)-1,2-Bis(4-chlorophenyl)ethane-1,2-diamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,2-bis(4-Chlorophenyl)ethane-1,2-diamine is used as a reactant in the synthesis of sinomenine derivatives exhibiting potent TNF-α inhibitory activity.

Technology Process of meso-1,2-Bis(4-chlorophenyl)ethylenediamine

There total 7 articles about meso-1,2-Bis(4-chlorophenyl)ethylenediamine 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%

4-chlorobenzaldehyde (104-88-1) → (1R,2S)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine (86212-34-2,91044-20-1,98674-96-5,74641-30-8)

Guidance literature:

4-chlorobenzaldehyde; With ammonium acetate; at 120 ℃; for 3h;

With sulfuric acid; water; at 170 ℃; for 12h;

DOI:10.1016/j.tetasy.2014.01.007

Reference yield: 50.0%

N-[1,2-bis(4-chlorophenyl)-2-[(E)-(4-chlorophenyl)methyleneamino]ethyl]-4-chlorobenz amide → (1R,2S)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine (86212-34-2,91044-20-1,98674-96-5,74641-30-8)

Guidance literature:

With sulfuric acid; In water; at 180 ℃; for 4h;

Reference yield: 47.0%

N-[1,2-bis(4-chlorophenyl)-2-[(E)-(4-chlorophenyl)methyleneamino]ethyl]-4-chlorobenzamide → (1R,2S)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine (86212-34-2,91044-20-1,98674-96-5,74641-30-8)

Guidance literature:

With sulfuric acid; for 1h; Reflux;

upstream raw materials:

4-chloro-benzoic acid-[erythro-4,4'-dichloro-α'-(4-chloro-benzylidenamino)-bibenzyl-α-ylamide]

(1E, 2E)-1,2-bis (4-chlorobenzylidene) hydrazine

4-chlorobenzaldoxime

4-chlorobenzaldehyde

Downstream raw materials:

4,5-di(p-chlorophenyl)imidazoline-2-thione

meso-4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-1H-imidazole

N-((1S,2R)-1,2-bis(4-chlorophenyl)-2-(pyrrolidin-1-yl)ethyl)benzamide

(1S,2R)-1,2-bis(4-chlorophenyl)-2-(pyrrolidin-1-yl)ethanamine

Refernces

• 1、 -. "Chiral synthesis method for producing cis-imidazoline compounds for pharmaceutical use". . . Retrieved 2018/06/19.
• 2、 -. "Dimer ester micromolecule PROTACs for inducing MDM2 to self-degrade E3 ubiquitin ligase". . . Retrieved 2018/10/19.