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

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

Uses

Used in Organic Chemistry:
DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE is used as a building block for the synthesis of complex organic molecules, contributing to the development of new compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE is used as an intermediate in the production of pharmaceutical compounds, facilitating the creation of new drugs with potential therapeutic benefits.
Used in Material Science:
DIETHYL 2-(2-THIENYLMETHYLIDENE)MALONATE is used as a component in the development of new materials, such as polymers and composites, that may have unique properties and applications in various fields.

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

• 1312929-66-0 (2S,3S)-1,1-diethyl 3-methyl 3-(diphenylmethyleneamino)-2-(thiophen-2-yl)propane-1,1,3-tricarboxylate 
• 1309167-09-6 2,3-diphenyl-5-(2-thienyl)-4,4-isoxazolidine-dicarboxylate 
• 1310582-81-0 C₃₆H₅₂N₂O₂S₃Si₂ 
• 1310582-87-6 bis[(S)-4-phenylthiazoline-2-yl]-2-thienylethene 
• 1310582-80-9 C₃₈H₅₆N₂O₂S₃Si₂ 
• 1310582-75-2 C₃₆H₅₂N₂O₄SSi₂ 
• 1310582-74-1 C₃₈H₅₆N₂O₄SSi₂ 
• 1310582-86-5 bis[(S)-4-benzylthiazoline-2-yl]-2-thienylethene 
• 1201653-19-1 (S,S)-N,N'-bis(2-hydroxy-1-phenyl)-2-(2-thienylmethylidene)malonamide 
• 1201653-17-9 (S,S)-N,N'-bis(2-hydroxy-1-benzyl)-2-(2-thienylmethylidene)malonamide 

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.

Method for preparing eprosartan intermediate by using reaction auxiliaries

The invention discloses a method for preparing an eprosartan intermediate diethyl 2-thienylidene malonate through using a reaction assistant. The method is characterized in that 2-thiophenecarboxaldehyde and diethyl malonate adopt cyclohexane as a reaction solvent, piperidine and benzoic acid are adopted as a catalyst, one or more ortho-formates is/are added into a reaction solution as the reaction assistant, and a reaction is carried out to obtain diethyl 2-thienylidene malonate. The synthetic method has the advantages of mild reaction conditions, simple process, short reaction time, few byproducts, good yield, and obtaining of a highly pure product.

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.

Knoevenagel condensation of diethylmalonate with aldehydes catalyzed by immobilized bovine serum albumin (BSA)

Knoevenagel condensation between aldehydes and diethylmalonate is catalyzed efficiently by bovine serum albumin (BSA) immobilized covalently on an epoxy-functionalized polymeric support, Immobead IB-350. The reaction is carried out conveniently at room temperature in DMSO in which aliphatic, heterocyclic and aromatic aldehydes react efficiently. After extraction with heptane and treatment with Candida antarctica lipase CAL B, the products are obtained in >95% purity and 85-89% yield. The solvent DMSO, unreacted diethylmalonate and immobilized BSA were easily recovered. Immobilized BSA and recovered DMSO were recycled 5 times without any appreciable loss in yield.

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.

Chiral-Zn(NTf2)2-complex-catalyzed diastereo- and enantioselective direct conjugate addition of arylacetonitriles to alkylidene malonates

Chiral N,N′-dioxide/Zn(NTf2)2 complexes were demonstrated to be highly effective in the direct asymmetric conjugate addition of arylacetonitriles to alkylidene malonates under mild conditions. A wide range of substrates were tolerated to afford their corresponding products in moderate-to-good yields with high diastereoselectivities (82:18->99:1 d.r.) and enantioselectivities (81-99 % ee). The reactions performed well, owing to the high Lewis acidity of the metal triflimidate and a ligand-acceleration effect. The N,N′-dioxide also benefited the deprotonation process as a Bronsted base. The catalytic reaction could be performed on the gram-scale with retention of yield, diastereoselectivity, and enantioselectivity. The products that contained functional groups were ready for further manipulation. In addition, a possible catalytic model was proposed to explain the origin of the asymmetric induction. Copyright

Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3a,4,6- tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates

A series of ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a- carboxylates were prepared through the metal-catalyzed domino reaction of alkylidene malonates and 1,4-butynediol under a one-pot reaction condition at room temperature. Their in vitro anti-proliferative activities were subsequently evaluated in A549, QGY and HeLa cells. The majority of the compounds showed potent anti-tumor activity against HeLa cells. In particular, compound 3l was the most potent compound with IC50 value of 5.4 μM. For the first time, the X-ray structure of the anti-tumor ethyl 3-aryl-4-oxo-3,3a,4,6- tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates is determined.

Rapid and regioselective hydrogenation of α,β-unsaturated ketones and alkylidene malonic diesters using Hantzsch ester catalyzed by titanium tetrachloride

A regioselective hydrogenation of α,β-unsaturated ketones and alkylidene malonic diesters using Hantzsch ester as the reducing agent and titanium tetrachloride as a catalyst is described. The short reaction times and mild reaction conditions are the advantages of this method. Georg Thieme Verlag Stuttgart New York.

Synthesis and biological evaluation of [carboxyl-11C]eprosartan

Essential hypertension occurs in approximately 25% of the adult population and one cause of hypertension is primary aldosteronism. Targeting the angiotensin II AT1 receptor using PET and an appropriate tracer may offer a diagnostic method for a

IMPROVED PROCESS FOR MANUFACTURING ANHYDROUS (E)-3-[2-BUTYL-1- {(4-CARBOXYPHENYL) METHYL}-1H-IMIDAZOLE-5-YL]-(THIOPHEN-2- YLMETHYL)PROP-2-ENOIC ACID METHANE SULFONATE

The present invention relates to a simple efficient and cost effective process for commercial manufacture of (E)-3-[2-Butyl-1-{(4-carboxyphenyl) methyl}-1H-imidazole-5-yl]- 2-(thiophen-2-ylmethyl)prop-2-enoic acid and its conversion to substantially pure