Diethyl (4-bromobenzylidene)malonate

Base Information

• Chemical Name: Diethyl (4-bromobenzylidene)malonate
• CAS No.: 22399-01-5
• Molecular Formula: C14H15BrO4
• Molecular Weight: 327.175
• NSC Number: 637153
• DSSTox Substance ID: DTXSID20327206
• Nikkaji Number: J638.198G
• ChEMBL ID: CHEMBL1362503
• Mol file: 22399-01-5.mol

Synonyms:diethyl (4-bromobenzylidene)malonate;diethyl 2-[(4-bromophenyl)methylidene]propanedioate;22399-01-5;MLS000756785;NSC637153;SR-01000076616;SR-01000076616-3;cid_367432;SCHEMBL1673521;CHEMBL1362503;BDBM62222;DTXSID20327206;HMS2886H18;propanedioic acid, [(4-bromophenyl)methylene]-, diethyl ester;DNDI1417400;AKOS002134081;Diethyl 2-(4-bromobenzylidene)malonate;NSC-637153;SMR000529064;4-Bromobenzylidenemalonic acid diethyl ester;2-(4-bromobenzylidene)malonic acid diethyl ester;diethyl 2-[(4-bromophenyl)methylene]propanedioate;2-(4-bromo-benzylidene)-malonic acid diethyl ester;SR-01000076616-1;2-[(4-bromophenyl)methylidene]propanedioic acid diethyl ester

Chemical Property of Diethyl (4-bromobenzylidene)malonate

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 326.01537
• Heavy Atom Count: 19
• Complexity: 323

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diethyl (4-bromobenzylidene)malonate

There total 8 articles about Diethyl (4-bromobenzylidene)malonate 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: 95.0%

4-bromo-benzaldehyde (1122-91-4) + Diethyl 2-bromomalonate (685-87-0) → diethyl 2-(4-bromobenzylidene)malonate (22399-01-5)

Guidance literature:

With tri-n-butylarsine; at 80 ℃; for 10h;

DOI:10.1016/0022-328X(89)85082-X

Reference yield: 81.0%

4-bromo-benzaldehyde (1122-91-4) + diethyl malonate (105-53-3) → diethyl 2-(4-bromobenzylidene)malonate (22399-01-5)

Guidance literature:

With indium(III) chloride; acetic anhydride; In toluene; at 70 ℃;

DOI:10.1039/c8tc06000b

Reference yield: 7.0%

4-bromo-benzaldehyde (1122-91-4) + diethyl malonate (105-53-3) → 4-Bromobenzoic acid (586-76-5) + diethyl 2-(4-bromobenzylidene)malonate (22399-01-5)

Guidance literature:

With bentonite Actisil FF; for 0.25h; Irradiation;

DOI:10.1080/00397919508011413

upstream raw materials:

4-bromo-benzaldehyde

diethyl malonate

Diethyl 2-bromomalonate

malonic acid dimethyl ester

Downstream raw materials:

(4S,5R)-4-(4-Bromo-phenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester

Refernces

• 1、 Riva, Laura,Punta, Carlo,Sacchetti, Alessandro. "Co-Polymeric Nanosponges from Cellulose Biomass as Heterogeneous Catalysts for amine-catalyzed Organic Reactions". . p. 6214 - 6222. Retrieved 2020/10/02.
• 2、 Moser, Maximilian,Thorley, Karl J.,Moruzzi, Floriana,Ponder, James F.,Maria, Iuliana P.,Giovannitti, Alexander,Inal, Sahika,McCulloch, Iain. "Highly selective chromoionophores for ratiometric Na+ sensing based on an oligoethyleneglycol bridged bithiophene detection unit". supporting information. p. 5359 - 5365. Retrieved 2019/05/21.