2,2-Dibromopropanoic acid ethyl ester

Base Information

• Chemical Name: 2,2-Dibromopropanoic acid ethyl ester
• CAS No.: 34757-17-0
• Molecular Formula: C5H8Br2O2
• Molecular Weight: 259.925
• DSSTox Substance ID: DTXSID50447764
• Nikkaji Number: J88.965B
• Wikidata: Q82266651
• Mol file: 34757-17-0.mol

Synonyms:ethyl 2,2-dibromopropionate;2,2-dibromo-propionic acid ethyl ester;2,2-Dibrom-propionsaeure-aethylester;Propanoic acid,2,2-dibromo-,ethyl ester;CH3CBr2CO2Et;ethyl dibromopropionate;

Chemical Property of 2,2-Dibromopropanoic acid ethyl ester

Chemical Property:

• Boiling Point: 49 °C(Press: 2.2 Torr)
• PSA: 26.30000
• Density: 1.843±0.06 g/cm3(Predicted)
• LogP: 2.05550
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 259.88706
• Heavy Atom Count: 9
• Complexity: 112

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(Br)Br

Technology Process of 2,2-Dibromopropanoic acid ethyl ester

There total 2 articles about 2,2-Dibromopropanoic acid ethyl ester 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: 85.0%

Ethyl 2-bromopropionate (535-11-5,41978-69-2) → ethyl 2,2-dibromopropanoate (34757-17-0)

Guidance literature:

Ethyl 2-bromopropionate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With 1,2-dibromo-1,1,2,2-tetrafluoroethane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1248/cpb.51.477

Reference yield: 75.0%

1,2-dibromo-1,1,2,2-tetrachloroethane (630-25-1) + Ethyl 2-bromopropionate (535-11-5,41978-69-2) → ethyl 2,2-dibromopropanoate (34757-17-0)

Guidance literature:

Ethyl 2-bromopropionate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -71 ℃; for 0.866667h; Inert atmosphere;

1,2-dibromo-1,1,2,2-tetrachloroethane; In tetrahydrofuran; hexane; at -71 ℃; for 0.666667h; Inert atmosphere;

DOI:10.15227/orgsyn.084.0011

Reference yield: 100.0%

ethyl 2,2-dibromopropanoate (34757-17-0) + 2-(N-benzyl-N-methylamino)-1-phenylpropan-1-one (16735-30-1) → 1,3,5-trimethyl-4-phenyl-1,5-dihydro-2-pyrrolone (73081-72-8)

Guidance literature:

ethyl 2,2-dibromopropanoate; With tert.-butyl lithium; In tetrahydrofuran; at -78 - 0 ℃; for 3.5h;

2-(N-benzyl-N-methylamino)-1-phenylpropan-1-one; In tetrahydrofuran; at 20 ℃; for 0.5h;

In tetrahydrofuran; at 20 ℃; Further stages.;

DOI:10.1002/chem.200500574

upstream raw materials:

Ethyl 2-bromopropionate

1,2-dibromo-1,1,2,2-tetrachloroethane

Downstream raw materials:

(Z)-2-methyl-3-trimethylsilyl-3-phenylpropenoic acid

(Z)-2-methyl-3-trimethylsilyl-4-phenyl-2-butenoic acid

3-(tert-butyl-dimethyl-silanyl)-2-methyl-4-phenyl-but-2-enoic acid

2-benzyl-3-ethyl-4-methylisoxazolidin-5-one

Refernces

The effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates

10.1016/j.tet.2009.08.060

The research investigates the effects of C–S and C–Se bonds on torquoselectivity in the olefination of α-thio and α-selenoketones with ynolates. The purpose is to achieve highly Z-selective olefination and understand the underlying mechanisms. The study found that the torquoselectivity is controlled by secondary orbital interactions between the s orbital of the C–S bond or a lone pair orbital on the sulfur and the s* orbitals of the breaking C–O bond, and vice versa. Key chemicals used include α-thioketones such as 2-(dodecylthio)-1-phenylpropan-1-one and α-selenoketones like 2-(phenylseleno)-1-phenylpropan-1-one, as well as ynolates derived from ethyl 2,2-dibromopropionate. The research concludes that these interactions significantly influence the stereoselectivity of the olefination process, providing new insights into torquoselectivity and its practical applications in organic synthesis.