111293-23-3

Basic information

• Product Name: (-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE
• Synonyms: (-)-BIS((S)-1-(ETHOXYCARBONYL)ETHYL) &;(-)-fumaric acid bis[(s)-1-(ethoxycarbonyl)ethyl] ester;(-)-Bis[(S)-1-(ethoxycarbonyl)ethyl] fumarate 97%;(-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE
• CAS NO: 111293-23-3
• Molecular Formula: C₁₄H₂₀O₈
• Molecular Weight: 316.3
• Mol File: 111293-23-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 151 °C0.4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.139 g/mL at 20 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.450
• BRN: 4201513
• CAS DataBase Reference: (-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE(111293-23-3)
• EPA Substance Registry System: (-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE(111293-23-3)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 111293-23-3(Hazardous Substances Data)

Usage

General Description

(-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE is a chemical compound containing two stereoisomers connected by a fumarate group. It is a fumaric acid derivative with a symmetric structure, and is commonly used in organic synthesis and pharmaceutical research. The compound has potential applications in drug development due to its ability to act as a chiral building block. It is also used in the production of various fine chemicals and pharmaceutical intermediates. The compound is characterized by its ethoxycarbonyl ethyl groups, which contribute to its stereochemistry and reactivity in chemical reactions. (-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE is a versatile compound with potential uses in both academic and industrial settings.

InChI:InChI=1/C14H20O8/c1-5-19-13(17)9(3)21-11(15)7-8-12(16)22-10(4)14(18)20-6-2/h7-10H,5-6H2,1-4H3/b8-7+/t9-,10-/m0/s1

Upstream product

• 687-47-8 (S)-Ethyl lactate 
• 627-63-4 fumaryl dichloride 
• 108-31-6 maleic anhydride 
• 97-64-3 ethyl 2-hydroxypropionate 

Downstream Products

• 142608-04-6 (1R,3R,4S)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (S)-1-ethoxycarbonyl-ethyl ester 
• 142696-88-6 (1S,3S,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (S)-1-ethoxycarbonyl-ethyl ester 
• 142608-03-5 (S)-2-{2-[(E)-Toluene-4-sulfonylimino]-acetoxy}-propionic acid ethyl ester 
• 111293-21-1 (1S,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid bis-((S)-1-ethoxycarbonyl-ethyl) ester 
• 111293-20-0 (1R,2R)-Cyclohex-4-ene-1,2-dicarboxylic acid bis-((S)-1-ethoxycarbonyl-ethyl) ester 

Relevant articles and documents

Simple and highly efficient chiral dopant molecules possessing both rod- and arch-like units

A simple chiral dopant molecule (R)-1 with both rod- and arch-like units was prepared, and extremely large helical twisting powers (+123 to +228 μm-1) in nematic liquid crystal phases were achieved. We have demonstrated that the introduction of an arch-like unit in addition to rod-like units is highly effective in controlling the helical molecular alignment. As an application of the dopant, induction of blue phases by addition of a small amount of it was achieved. This journal is the Partner Organisations 2014.

Enantioselective synthesis of dual 5-HT4/5-HT3 serotonergic azanoradamantane SC-52491

A racemic synthesis of azanoradamantane (±)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e.