2-(2-Chloro-benzylidene)-3-oxo-butyric acid methyl ester

Base Information

• Chemical Name: 2-(2-Chloro-benzylidene)-3-oxo-butyric acid methyl ester
• CAS No.: 67593-46-8
• Molecular Formula: C12H11ClO3
• Molecular Weight: 238.671
• NSC Number: 172863
• DSSTox Substance ID: DTXSID401201843
• Mol file: 67593-46-8.mol

Synonyms:67593-46-8;2-(2-Chloro-benzylidene)-3-oxo-butyric acid methyl ester;2-Acetyl-3-(2-chlorophenyl)-acrylacidmethylester;NSC172863;SCHEMBL3194980;DTXSID401201843;AKOS015963359;AKOS025311599;NSC-172863;AC-19468;Methyl (2Z)-2-[(2-chlorophenyl)methylene]-3-oxobutanoate;1170036-31-3

Chemical Property of 2-(2-Chloro-benzylidene)-3-oxo-butyric acid methyl ester

Chemical Property:

• Vapor Pressure: 5.46E-05mmHg at 25°C
• Refractive Index: 1.564
• Boiling Point: 347.2 °C at 760 mmHg
• Flash Point: 142.6 °C
• PSA: 43.37000
• Density: 1.241 g/cm³
• LogP: 2.48540
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 238.0396719
• Heavy Atom Count: 16
• Complexity: 309

Purity/Quality:

99% ^*data from raw suppliers

2-(2-Chloro-benzylidene)-3-oxo-butyricacidmethylester 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(=CC1=CC=CC=C1Cl)C(=O)OC
• Isomeric SMILES: CC(=O)/C(=C/C1=CC=CC=C1Cl)/C(=O)OC

Technology Process of 2-(2-Chloro-benzylidene)-3-oxo-butyric acid methyl ester

There total 3 articles about 2-(2-Chloro-benzylidene)-3-oxo-butyric acid methyl 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: 84.0%

2-chloro-benzaldehyde (89-98-5) + acetoacetic acid methyl ester (105-45-3) → methyl 2-(2-chlorophenylmethylene)acetoacetate (67593-46-8)

Guidance literature:

With piperidine; acetic acid; In benzene; for 4h; Ambient temperature;

DOI:10.1248/cpb.34.1589

Reference yield:

methanolic dimethylamine + 2-chloro-benzaldehyde (89-98-5) + acetoacetic acid methyl ester (105-45-3) → methyl 2-(2-chlorophenylmethylene)acetoacetate (67593-46-8)

Guidance literature:

With acetic acid; In ethyl acetate; isopropyl alcohol;

Reference yield:

2-chloro-benzaldehyde (89-98-5) + acetoacetic acid methyl ester (105-45-3) → methyl (E)-2-acetyl-3-(2-chlorophenyl)acrylate + methyl (Z)-2-acetyl-3-(2-chlorophenyl)acrylate (67593-46-8)

Guidance literature:

With [Pip][OAc]; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 20 ℃; for 5h; Title compound not separated from byproducts;

DOI:10.1007/s11172-005-0386-1

upstream raw materials:

2-chloro-benzaldehyde

acetoacetic acid methyl ester

Downstream raw materials:

4-(2-chloro-phenyl)-2,6-bis-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine

2-(2-azidoethoxy)methyl-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

4-(2-Chloro-phenyl)-2-methyl-6-(2-morpholin-4-yl-ethoxymethyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-ethyl ester 3-methyl ester

Refernces

• 1、 Putilova,Troitskii,Zlotin. "Reaction of aromatic aldehydes with β-dicarbonyl compounds in a catalytic system: Piperidinium acetate - 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid". . p. 1233 - 1238. Retrieved 2007/10/03.
• 2、 Ohno,Komatsu,Mizukoshi,Ichihara,Nakamura,Morishima,Sumita. "Synthesis of asymmetric 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates with vasodilating and antihypertensive activities". . p. 1589 - 1606. Retrieved 2007/10/02.