3-(4-Bromobenzylidene)-2,4-pentanedione

Base Information

• Chemical Name: 3-(4-Bromobenzylidene)-2,4-pentanedione
• CAS No.: 15795-19-4
• Molecular Formula: C12H11BrO2
• Molecular Weight: 267.122
• NSC Number: 637174
• DSSTox Substance ID: DTXSID60876708
• Nikkaji Number: J1.606.720B
• Mol file: 15795-19-4.mol

Synonyms:3-(4-Bromobenzylidene)-2,4-pentanedione;NSC637174;15795-19-4;3-[(4-bromophenyl)methylidene]pentane-2,4-dione;SCHEMBL12630700;DTXSID60876708;ACETYLACETONE,4-BROMOBENZAL;STL025733;AKOS005641727;NSC-637174;3-(4-bromobenzylidene)pentane-2,4-dione;2,4-Pentanedione, 3-(p-bromobenzylidene)-;3-[(4-bromophenyl)methylene]pentane-2,4-dione;2,4-Pentanedione, 3-[(4-bromophenyl)methylene]-;Z227968430

Chemical Property of 3-(4-Bromobenzylidene)-2,4-pentanedione

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 265.99424
• Heavy Atom Count: 15
• Complexity: 270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C(=CC1=CC=C(C=C1)Br)C(=O)C

Technology Process of 3-(4-Bromobenzylidene)-2,4-pentanedione

There total 2 articles about 3-(4-Bromobenzylidene)-2,4-pentanedione 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: 89.0%

4-bromo-benzaldehyde (1122-91-4) + acetylacetone (123-54-6,81235-32-7) → 4'-bromo-3-benzylidene-2,4-pentanedione (15795-19-4)

Guidance literature:

With L-proline; at 20 ℃; for 0.333333h;

DOI:10.1016/j.tetlet.2008.12.036

Reference yield:

→ 4'-bromo-3-benzylidene-2,4-pentanedione (15795-19-4)

Guidance literature:

4-Brom-benzaldehyd, Pentan-2,4-dion, Ggw. v. Piperidin u. Eg., Bzl., Erwaermen;

DOI:10.1139/v67-166

Reference yield: 94.0%

diazoacetic acid ethyl ester (623-73-4) + 4'-bromo-3-benzylidene-2,4-pentanedione (15795-19-4) → trans-4-acetyl-3-(4-bromophenyl)-5-methyl-2,3-dihydrofuran-2-carboxylic acid ethyl ester

Guidance literature:

With pyridine; 5,10,15,20-tetrakis(p-chlorophenyl)porphyrin iron(III) chloride; In toluene; at 40 ℃; for 3h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/c0cc02347g

upstream raw materials:

4-bromo-benzaldehyde

acetylacetone

Downstream raw materials:

(2S,3S)-ethyl 4-acetyl-3-(4-bromophenyl)-5-methyl-2,3-dihydrofuran-2-carboxylate

p-BrC₆H₄CHC(CMeNNHPh)2

Refernces

• 1、 Worgull, Dennis,?hler, Laura,Strache, Joss Pepe,Friedrichs, Teresa,Ullrich, Patrick. "Enantioselective Synthesis of 2,3-Dihydrofurans via Ammonium Ylides". . p. 6077 - 6080. Retrieved 2017.
• 2、 Zhang, Fuyi,Wang, Yu-Xin,Yang, Feng-Ling,Zhang, Hong-Yu,Zhao, Yu-Fen. "Efficient solvent-free knoevenagel condensation between -diketone and aldehyde catalyzed by silica sulfuric acid". scheme or table. p. 347 - 356. Retrieved 2011/04/16.