Di-(4-chlorobenzyl)azodicarboxylate

Base Information

• Chemical Name: Di-(4-chlorobenzyl)azodicarboxylate
• CAS No.: 916320-82-6
• Molecular Formula: C₁₆H₁₂Cl₂N₂O₄
• Molecular Weight: 367.188
• European Community (EC) Number: 693-431-4
• Mol file: 916320-82-6.mol

Synonyms:Di-(4-chlorobenzyl)azodicarboxylate;DCAD;Bis(4-chlorobenzyl)azodicarboxylate;(4-chlorophenyl)methyl (NZ)-N-[(4-chlorophenyl)methoxycarbonylimino]carbamate;916320-82-6;AKOS037652917;FS-3889;Di-(4-chlorobenzyl)azodicarboxylate, 97%

Chemical Property of Di-(4-chlorobenzyl)azodicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 108-112°C
• Refractive Index: 1.592
• Boiling Point: 505.576 °C at 760 mmHg
• Flash Point: 259.563 °C
• PSA: 77.32000
• Density: 1.366 g/cm³
• LogP: 5.41900
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 366.0174123
• Heavy Atom Count: 24
• Complexity: 405

Purity/Quality:

98%,99%, ^*data from raw suppliers

Di-(4-chlorobenzyl)azodicarboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1COC(=O)N=NC(=O)OCC2=CC=C(C=C2)Cl)Cl
• Isomeric SMILES: C1=CC(=CC=C1COC(=O)/N=N\C(=O)OCC2=CC=C(C=C2)Cl)Cl
• Uses: Reactant for preparation of:Amino thioesters via guanidine-catalyzed biomimetic enantioselective decarboxylative Mannich and amination reactions of malonic acid half thioestersHydroacylation reaction of aldehydes in Ionic liquid (IL) mediumDCAD (di-p-chlorobenzyl azodicarboxylate) for Mitsunobu coupling reactions

Technology Process of Di-(4-chlorobenzyl)azodicarboxylate

There total 3 articles about Di-(4-chlorobenzyl)azodicarboxylate 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: 99.0%

bis(4-chlorobenzyl) hydrazine-1,2-dicarboxylate → bis(4-chlorobenzyl) diazene-1,2-dicarboxylate (916320-82-6)

Guidance literature:

With pyridine; N-Bromosuccinimide; In toluene; at 20 ℃; for 2h;

DOI:10.1055/s-0028-1083274

Reference yield:

imidazole-1-carboxylic acid 4-chloro-benzyl ester → bis(4-chlorobenzyl) diazene-1,2-dicarboxylate (916320-82-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.96 g / NH₂NH₂; Et₃N / 7.5 h / Heating

2: 98 percent / pyridine; NBS / toluene / 0.28 h / 20 °C

With pyridine; N-Bromosuccinimide; triethylamine; hydrazine; In toluene;

DOI:10.1021/ol0618757

Reference yield:

para-Chlorobenzyl alcohol (873-76-7) → bis(4-chlorobenzyl) diazene-1,2-dicarboxylate (916320-82-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 1 h / 0 - 20 °C

2: 2.96 g / NH₂NH₂; Et₃N / 7.5 h / Heating

3: 98 percent / pyridine; NBS / toluene / 0.28 h / 20 °C

With pyridine; N-Bromosuccinimide; triethylamine; hydrazine; In tetrahydrofuran; toluene;

DOI:10.1021/ol0618757

upstream raw materials:

para-Chlorobenzyl alcohol

Refernces

• 1、 Lipshutz, Bruce H.,Chung, David W.,Rich, Brian,Corral, Ricardo. "Simplification of the Mitsunobu reaction. Di-p-chlorobenzyl azodicarboxylate: A new azodicarboxylate". . p. 5069 - 5072. Retrieved 2007/10/03.