Butanedioic acid, propylidene-, dimethyl ester

Base Information

• Chemical Name: Butanedioic acid, propylidene-, dimethyl ester
• CAS No.: 139474-72-9
• Molecular Formula: C9H14O4
• Molecular Weight: 186.20500
• Mol file: 139474-72-9.mol

Synonyms:(E)-dimethyl 2-propylidenesuccinate;Propyliden-bernsteinsaeure-dimethylester;propylidene-succinic acid dimethyl ester;dimethyl (2E)-2-propylidenesuccinate;Butanedioic acid,propylidene-,dimethyl ester;dimethyl (E)-2-(propylidene)succinate;Penten-(2)-dicarbonsaeure-(1.2)-dimethylester;

Chemical Property of Butanedioic acid, propylidene-, dimethyl ester

Chemical Property:

• Boiling Point: 78.5-80 °C(Press: 1.25 Torr)
• PSA: 52.60000
• Density: 1.0746 g/cm3
• LogP: 1.05890

Purity/Quality:

DimethylPropylidenesuccinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Dimethyl Propylidenesuccinate is an intermediate in the synthesis of 2-Ethyl-3-methylmaleic Anhydride (E923520). 2-Ethyl-3-methylmaleic Anhydride is one of the bioactive ingredients present in essential oil of the leaves of Maytenus obtusifolia (Celastraceae), showed antimicrobial activity against 13 strains of bacteria, and fungus and yeast. The oil showed significant antimicrobial activity against Sthaphylococcus aureus (ATCC 6538), Escherichia coli (ATCC 18739), Listeria monocytogenes (ATCC 9610), Candida albicans (ATCC 13803), Candida tropicalis (LM 37), Candida guilliermondii (LM V70) and Aspergillus flavus (LM 247).

Technology Process of Butanedioic acid, propylidene-, dimethyl ester

There total 5 articles about Butanedioic acid, propylidene-, dimethyl 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: 91.0%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) + 1-Nitropropane (108-03-2) → dimethyl (E)-2-(propylidene)succinate (139474-72-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 0.25h; Ambient temperature;

DOI:10.1016/0040-4039(94)88479-X

Reference yield: 91.0%

1-Nitropropane (108-03-2) + dimethylfumarate (624-49-7) → dimethyl (E)-2-(propylidene)succinate (139474-72-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1002/1099-0690(200008)2000:16<2927::aid-ejoc2927>3.3.co;2-p

Reference yield: 72.0%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) + propionaldehyde (123-38-6) → dimethyl (E)-2-(propylidene)succinate (139474-72-9)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0030-1260013

upstream raw materials:

dimethyl cis-but-2-ene-1,4-dioate

1-Nitropropane

dimethylfumarate

propionaldehyde

Downstream raw materials:

propyl-succinic acid

Refernces

• 1、 Ballini, Roberto,Rinaldi, Alessandro. "Michael Addition of Nitroalkanes to Dimethyl Maleate with DBU. A New Direct Method for the Synthesis of Polyfunctionalized α,β-Unsaturated Esters.". . p. 9247 - 9250. Retrieved 1994.
• 2、 Kshirsagar, Umesh A.,Argade, Narshinha P.. "Regioselective monoalkylation of dimethyl alkylidenesuccinates: Simple approach to dialkyl-substituted maleic anhydrides including chaetomellic acid A". experimental part. p. 1804 - 1808. Retrieved 2011/07/29.
• 3、 Ruan, Jiwu,Lu, Gui,Xu, Lijing,Li, Yue-Ming,Chan, Albert S. C.. "Catalytic asymmetric alkynylation and arylation of aldehydes by an H 8-binaphthyl-based amino alcohol ligand". experimental part. p. 76 - 84. Retrieved 2009/04/11.