30313-06-5

Basic information

• Product Name: DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE
• Synonyms: DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE;(2-thenylidene)-malonicacidiethylester;DIETHYL 2-THIENYLIDENE MALONATE;[(2-Thienyl)methylene]malonic acid diethyl ester;2-Thenylidenemalonic acid diethyl ester;diethyl (thiophen-2-ylmethylidene)propanedioate;Diethyl 2-thienylmethylidenemalonate
• CAS NO: 30313-06-5
• Molecular Formula: C₁₂H₁₄O₄S
• Molecular Weight: 254.3
• Mol File: 30313-06-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 320.4°Cat760mmHg
• Flash Point: 147.6°C
• Appearance: /
• Density: 1.215g/cm³
• Vapor Pressure: 0.000318mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE(30313-06-5)
• EPA Substance Registry System: DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE(30313-06-5)

Safety Data

• Hazardous Substances Data: 30313-06-5(Hazardous Substances Data)

Usage

General Description

DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE is a chemical compound that belongs to the category of thienyl compounds, which contain a thiophene ring. Thiophene is a heterocyclic compound with the formula C4H4S. The compound DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE is utilized in the field of organic chemistry to produce complex organic molecules. It is necessary to handle this chemical with precise care as there may be safety and hazards associated with it, just like with any other chemicals. Detailed data including the physical and chemical properties, safety, hazards, toxicity, and synthetic procedure of this chemical can be found in the Material Safety Data Sheet (MSDS).

InChI:InChI=1/C12H14O4S/c1-3-15-11(13)10(12(14)16-4-2)8-9-6-5-7-17-9/h5-8H,3-4H2,1-2H3

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 105-53-3 diethyl malonate 

Downstream Products

• 133485-98-0 2-[2-Butyl-5-((E)-2-carboxy-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid 
• 133485-77-5 SKF 108834 
• 143468-96-6 3-ethoxy-3-oxo-2-(thien-3-ylmethyl)propanoic acid 
• 133485-84-4 (E)-3-[2-n-butyl-1-{(2,3-dichlorophenyl)methyl}-1H-imidazol-5-yl]-2-(thien-2-yl)methyl-2-propenoic acid 

Relevant articles and documents

Synthesis of two precursors of heterocarbocyclic nucleoside analogues

The racemic heterobicyclic amino alcohols 6 and 7, which are of interest as intermediates in the synthesis of nucleoside analogues with heterobicyclic pseudosugars, were efficiently prepared from 2-thienylsuccinic acid via methyl 4-hydroxyimino-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylate [(±)-14]. The target compounds were obtained together by direct reduction of (±)-14 with AlH3 in refluxing THF, and were separated by flash chromatography of their N-acetylated derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Preparation method of improved eprosartan intermediate

The invention discloses a method for preparing an eprosartan intermediate 2-thenylidene diethyl malonate. The method comprises the steps of adopting 2-thiophenecarboxaldehyde and diethyl malonate as starting raw materials; under co-catalysis of acid-base, adopting cyclohexane as a reaction solvent, adopting a strong-polar aprotic organic solvent as a solvent additive, and preparing to obtain the eprosartan intermediate 2-thenylidene diethyl malonate. According to the method provided by the invention, the reaction time can be greatly shortened, and the eprosartan intermediate 2-thenylidene diethyl malonate with high purity can be obtained.

Nickel(ii)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine imines with alkylidene malonates

We demonstrated an asymmetric 1,3-dipolar cycloaddition of azomethine betaines with alkylidene malonates by using a chiral N,N'-dioxide- NiII complex as a catalyst. Both aromatic- and aliphatic-substituted alkylidene malonates were found to be suitable for the reaction. A range of transpyrazolone derivatives was exclusively obtained with excellent yields (up to 99% yield) and good enantioselectivities (up to 97% ee) under mild reaction conditions. The reaction could be carried out on a gram scale with the good results being maintained. Control experiments were performed to elucidate the specific diastereoselectivity of the reaction. The formation of single trans isomers was dominated by secondary orbital interactions between the ester groups of the dipolarophile and the azomethine imine. On the basis of the experimental results and previous reports, a possible catalytic model was assumed.