Dimethyl (p-methoxybenzylidene)malonate

Base Information

• Chemical Name: Dimethyl (p-methoxybenzylidene)malonate
• CAS No.: 7443-25-6
• Molecular Formula: C13H14O5
• Molecular Weight: 250.251
• Hs Code.: 2918990090
• European Community (EC) Number: 231-185-8
• NSC Number: 306435
• UNII: VXO4D73WEH
• DSSTox Substance ID: DTXSID5042328
• Nikkaji Number: J76.672K
• Wikidata: Q27292078
• ChEMBL ID: CHEMBL2148174
• Mol file: 7443-25-6.mol

Synonyms:7443-25-6;Dimethyl (p-methoxybenzylidene)malonate;Dimethyl (4-methoxybenzylidene)malonate;Cyasorb UV 1988;dimethyl 2-[(4-methoxyphenyl)methylidene]propanedioate;Propanedioic acid, [(4-methoxyphenyl)methylene]-, dimethyl ester;Dimethyl 2-(4-Methoxybenzylidene)Malonate;UNII-VXO4D73WEH;VXO4D73WEH;CHEMBL2148174;EINECS 231-185-8;Malonic acid, (p-methoxybenzylidene)-, dimethyl ester;NSC 306435;NSC-306435;Propanedioic acid, ((4-methoxyphenyl)methylene)-, dimethyl ester;Propanedioic acid, 2-((4-methoxyphenyl)methylene)-, 1,3-dimethyl ester;dimethyl 4-methoxybenzylidenemalonate;SANDUVOR PR 25;dimethyl 4-methoxy benzylidene malonate;SCHEMBL77601;DTXSID5042328;dimethyl p-methoxybenzylidenemalonate;BDBM50391676;MFCD09753105;NSC306435;AKOS000264909;Dimethyl2-(4-Methoxybenzylidene)Malonate;AS-64110;D5642;p-methoxybenzylidenemalonic acid dimethyl ester;D90415;Q27292078;((4-METHOXYPHENYL)METHYLENE)MALONIC ACID DIMETHYL ESTER;2-[(4-methoxyphenyl)methylene]propanedioic acid, dimethyl ester;1,3-DIMETHYL 2-[(4-METHOXYPHENYL)METHYLIDENE]PROPANEDIOATE

Chemical Property of Dimethyl (p-methoxybenzylidene)malonate

Chemical Property:

• Vapor Pressure: 0.00012mmHg at 25°C
• Melting Point: 56-57℃
• Refractive Index: 1.54
• Boiling Point: 335.5 °C at 760 mmHg
• Flash Point: 145.9 °C
• PSA: 61.83000
• Density: 1.187 g/cm³
• LogP: 1.42460
• Solubility.: soluble in Methanol
• Water Solubility.: 91mg/L at 20℃
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 250.08412354
• Heavy Atom Count: 18
• Complexity: 308

Purity/Quality:

99.83% ^*data from raw suppliers

Dimethyl 2-(4-Methoxybenzylidene)malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=C(C(=O)OC)C(=O)OC
• Uses: Dimethyl 4-methoxybenzylidene malonate is an organic carboxylic acid ester, mainly used as an ultraviolet absorber.

Technology Process of Dimethyl (p-methoxybenzylidene)malonate

There total 6 articles about Dimethyl (p-methoxybenzylidene)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: 93.0%

4-methoxy-benzaldehyde (123-11-5) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-(4-methoxybenzylidene)malonate (7443-25-6)

Guidance literature:

With piperidine; acetic acid; In toluene; for 24h; Inert atmosphere; Molecular sieve; Dean-Stark; Reflux;

DOI:10.1002/ejoc.201701058

Reference yield: 89.0%

dimethyl diazomalonate (6773-29-1) + 4-methoxy-benzaldehyde (123-11-5) → dimethyl 2-(4-methoxybenzylidene)malonate (7443-25-6)

Guidance literature:

With tributylstibine; copper(l) iodide; In benzene; at 80 ℃; for 6h;

DOI:10.1016/S0040-4039(00)97988-7

Reference yield: 80.0%

N-(p-methoxybenzylidene)-p-aminoacetophenone (23596-02-3) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-(4-methoxybenzylidene)malonate (7443-25-6)

Guidance literature:

With pyridine; In benzene; at 20 ℃; chemoselective reaction; Heating;

upstream raw materials:

4-methoxy-benzaldehyde

malonic acid dimethyl ester

dimethyl diazomalonate

N-(p-methoxybenzylidene)-p-aminoacetophenone

Downstream raw materials:

2-[2-(2-Chloro-6-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

2-[2-(2,6-Dinitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

[2-(5-trifluoromethyl-2-nitrophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid,dimethyl ester

2-[2-(2-Methoxy-6-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

Refernces

• 1、 Khaligh, Nader Ghaffari,Gorjian, Hayedeh,Fahim, Hoda,Titinchi, Salam J. J.. "Solid-phase synthesis of arylidene and alkylidene malonates, as versatile intermediates, catalyzed using mesoporous poly-melamine–formaldehyde as a nitrogen-rich porous organic polymer (POP)". . p. 3529 - 3536. Retrieved 2021/05/11.
• 2、 Chan, Wei Chuen,Vinod, Jincy K.,Koide, Kazunori. "Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step". . p. 3674 - 3682. Retrieved 2021/02/16.