37784-67-1

Basic information

• Product Name: diethyl (3-thienyl)malonate
• Synonyms: diethyl (3-thienyl)malonate;2-(3-Thienyl)malonic acid diethyl ester;3-Thienylpropanedioic acid diethyl ester;Propanedioic acid, 3-thienyl-, diethyl ester;diethyl 2-(thiophen-3-yl)malonate
• CAS NO: 37784-67-1
• Molecular Formula: C₁₁H₁₄O₄S
• Molecular Weight: 242.29146
• EINECS: 253-666-1
• Mol File: 37784-67-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 312.5°C at 760 mmHg
• Flash Point: 142.8°C
• Appearance: /
• Density: 1.199
• Vapor Pressure: 0.000527mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: diethyl (3-thienyl)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (3-thienyl)malonate(37784-67-1)
• EPA Substance Registry System: diethyl (3-thienyl)malonate(37784-67-1)

Safety Data

• Hazardous Substances Data: 37784-67-1(Hazardous Substances Data)

Usage

Description

Diethyl (3-thienyl)malonate is a chemical compound with the molecular formula C11H14O4S. It is a malonate ester with a 3-thienyl group and two ethyl groups attached to the central malonate moiety. This colorless to pale yellow liquid at room temperature has a fruity odor and is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and organic compounds. Its versatile reactivity and potential biological activities make it a valuable compound in the field of medicinal chemistry for the development of new drugs and treatments.

Uses

Used in Pharmaceutical Industry:
Diethyl (3-thienyl)malonate is used as a key intermediate in the synthesis of various pharmaceuticals for its versatile reactivity and potential biological activities, contributing to the development of new drugs and treatments.
Used in Agrochemical Industry:
Diethyl (3-thienyl)malonate is utilized as a building block in the creation of agrochemicals, playing a crucial role in the development of effective and innovative products for agricultural applications.
Used in Organic Synthesis:
Diethyl (3-thienyl)malonate serves as a valuable intermediate in organic synthesis, enabling the production of a wide range of organic compounds for various industrial and research purposes.

InChI:InChI=1/C11H14O4S/c1-3-14-10(12)9(11(13)15-4-2)8-5-6-16-7-8/h5-7,9H,3-4H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 21080-92-2 2-(thiophen-3-yl)malonic acid 
• 13781-53-8 (thiophen-3-yl)acetonitrile 
• 872-31-1 3-Bromothiophene 
• 105-53-3 diethyl malonate 
• 21418-54-2 ethyl 3-thienyl-α-cyanoacetate 
• 7787-70-4 copper(I) bromide 
• 10486-61-0 3-thienyl iodide 
• 37784-63-7 ethyl-3 thiophene acetate 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 182952-28-9 2,3-Bis-ethoxycarbonyl-2,3-di-thiophen-3-yl-succinic acid diethyl ester 
• 182952-30-3 benzo[1,2-b;4,5-b']dithiophene-4,4,8,8-tetracarboxylic acid tetraethyl ester 
• 21080-92-2 2-(thiophen-3-yl)malonic acid 
• 99727-96-5 2-allyl-3-methylthiophene 

Relevant articles and documents

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Oxidative dimerization of diethyl 3-thienylmalonate by high valent metal salts. Synthesis of benzo[1,2-b:4,5-b']dithiophene derivatives

The oxidation of diethyl 3-thienylmalonate (1) by metal oxidants (Fe(ClO4)3, Mn(OAc)3, MnO2 and CuO) in various solvents at 60 °C affords dimerization products arising from side-chain and nuclear coupling of the intermediate delocalized malonyl radicals 6. Metal to sulphur binding is suggested to play a role in controlling the distribution of dimers 2-5. The higher thermodynamic stability of unsymmetric dimer 3, along with its oxidative intramolecular 1,6-cyclization to 4, allows to develop a new simple synthesis of benzo[1,2-b:4,5-b']dithiophene derivatives 15-18.

Chemical process

An improved process for the preparation of 3-substituted thiophenes. The thiophenes are useful for the preparation of penicillins and cephalosporins. The process is for the preparation of a thiophene of formula (I): STR1 where R1 represents a carboxylic acid group, or an ester or amide thereof or a nitrile group; R2 represents a group suitable for use as an α-substituent in the side-chain of a penicillin or cephalosporin; which comprises treating under basic conditions a compound of formula (II): STR2 wherein X represents halogen or optionally functionalized hydroxyl, Y represents halogen, hydroxyl, or alkoxy; with a source of nucleophilic sulphur ionically bound to a polymeric support.