Diethyl meso-2,3-dibromosuccinate

Base Information

• Chemical Name: Diethyl meso-2,3-dibromosuccinate
• CAS No.: 1114-31-4
• Molecular Formula: C₈H₁₂Br₂O₄
• Molecular Weight: 331.989
• DSSTox Substance ID: DTXSID70358282
• Nikkaji Number: J505.792B
• Wikidata: Q96235730
• Mol file: 1114-31-4.mol

Synonyms:DTXSID70358282;Diethyl meso-2,3-dibromosuccinate;1114-31-4;(2R,3S)-2,3-Dibromosuccinic acid diethyl ester

Chemical Property of Diethyl meso-2,3-dibromosuccinate

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 331.90818
• Heavy Atom Count: 14
• Complexity: 186

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(C(=O)OCC)Br)Br
• Isomeric SMILES: CCOC(=O)[C@@H]([C@@H](C(=O)OCC)Br)Br

Technology Process of Diethyl meso-2,3-dibromosuccinate

There total 14 articles about Diethyl meso-2,3-dibromosuccinate 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: 94.0%

diethyl Fumarate (623-91-6) → diethyl 2,3-dibromosuccinate (1114-30-3,1114-31-4,40205-59-2,608-82-2)

Guidance literature:

With tetra-N-butylammonium tribromide; In chloroform; for 0.25h;

Reference yield: 82.0%

but-2-enedioic acid diethyl ester (1520-50-9) → diethyl 2,3-dibromosuccinate (1114-30-3,1114-31-4,40205-59-2,608-82-2)

Guidance literature:

With maghemite(γ-Fe₂O₃) nanoparticle supported 2,2'-bis[3-(triethoxysilyl)propyl]imidazolium substituted diethyl ether bis(tribromide); In methanol; dichloromethane; for 6h; Reflux;

DOI:10.1002/ejic.201300755

Reference yield:

diethyl (2R,3R)-tartrate (87-91-2) → diethyl 2,3-dibromosuccinate (1114-30-3,1114-31-4,40205-59-2,608-82-2)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; at 98 ℃; for 4h; Schlenk technique; Inert atmosphere;

DOI:10.1039/d1ob00379h

upstream raw materials:

Diethyl maleate

diethyl Fumarate

ethanol

bromine

Downstream raw materials:

diethyl Fumarate

tetraethyl ethane-1,1,2,2-tetracarboxylate

Diethyl maleate

4-oxo-pentane-1,2,3-tricarboxylic acid triethyl ester

Refernces

• 1、 Wu, Liqiang,Yin, Zhikui. "Magnetic-nanoparticle-supported 2,2′-bis[3-(triethoxysilyl)propyl] imidazolium-substituted diethyl ether bis(tribromide): A convenient recyclable reagent for bromination". . p. 6156 - 6163. Retrieved 2014/01/06.
• 2、 Fournier, M.,Fournier, F.,Berthelot, J.. "UNE NOUVELLE METHODE DE BROMATION : LE TRIBROMURE DE TETRABUTYLAMMONIUM.". . p. 157 - 158. Retrieved 2007/10/02.