1476-06-8

Basic information

• Product Name: (2E)-1-ethoxybut-2-ene
• Synonyms: (2E)-1-Ethoxybut-2-ene; (2E)-But-2-en-1-yl ethyl ether; 2-butene, 1-ethoxy-, (2E)-
• CAS NO: 1476-06-8
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.1589
• Mol File: 1476-06-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 95.8°C at 760 mmHg
• Density: 0.785g/cm³
• Vapor Pressure: 51mmHg at 25°C
• Refractive Index: 1.41
• CAS DataBase Reference: (2E)-1-ethoxybut-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-ethoxybut-2-ene(1476-06-8)
• EPA Substance Registry System: (2E)-1-ethoxybut-2-ene(1476-06-8)

Safety Data

• Hazardous Substances Data: 1476-06-8(Hazardous Substances Data)

Usage

Description

(2E)-1-ethoxybut-2-ene, also known as (E)-1-Ethoxy-2-butene and Ethyl vinyl ether, is a colorless liquid chemical compound with the molecular formula C6H12O. It features a butene chain with an ethoxy group attached to the second carbon atom and has a cis configuration at the double bond. Known for its sweet, fruity odor, this compound is commonly used as a solvent or as an intermediate in the production of other chemicals. It can undergo polymerization or be utilized in reactions such as the Wittig reaction to form different compounds. Due to its flammable and hazardous nature, it is crucial to handle (2E)-1-ethoxybut-2-ene with care.

Uses

Used in Chemical Synthesis:
(2E)-1-ethoxybut-2-ene is used as an intermediate in the chemical synthesis industry for the production of various compounds. Its ability to undergo polymerization and participate in reactions like the Wittig reaction makes it a valuable component in creating a range of chemical products.
Used in Solvent Applications:
In the chemical industry, (2E)-1-ethoxybut-2-ene is utilized as a solvent for various processes. Its properties as a colorless liquid with a sweet, fruity odor make it suitable for dissolving substances in a controlled environment, facilitating different stages of chemical production and processing.
Used in Polymerization Processes:
(2E)-1-ethoxybut-2-ene is used as a monomer in polymerization processes to form polymers with specific properties. Its structure allows it to be polymerized into long chains, which can be used in the production of plastics, rubbers, and other materials with diverse applications.
Used in Research and Development:
Due to its unique chemical properties and reactivity, (2E)-1-ethoxybut-2-ene is employed in research and development settings to explore new chemical reactions, synthesize novel compounds, and study the behavior of molecules in various conditions.

Upstream product

• 64-17-5 ethanol 
• 4894-61-5 trans-but-2-enyl chloride 
• 598-32-3 2-hydroxy-3-butene 
• 106-99-0 buta-1,3-diene 
• 63511-92-2 (E)-crotonaldehyde diethyl acetal 
• 141-52-6 sodium ethanolate 
• 504-61-0 (E)-but-2-enol 
• 75-03-6 ethyl iodide 

Downstream Products

• 104684-95-9 1-(1-ethoxy-1-buten-3-yl)cyclohexanol 
• 6986-47-6 3-chloro-4-ethoxybutan-2-one 
• 628-81-9 butyl ethyl ether 

Relevant articles and documents

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The carbonylation of allylic halides and prop-2-en-1-ol catalysed by triethylphosphine complexes of rhodium

In ethanol, [RhX(CO)(PEt3)2] added directly or formed in situ from [Rh2(OAc)4]·2MeOH (OAc = O2CMe) and PEt3 or [Rh(OAc)(CO)(PEt3)2] catalysed the carbonylation of CH2=CHCH2X (X = Cl, Br or I) to ethyl but-3-enoate with CH2=CHCH2OEt as a side product. Small amounts of the isomerisation product, ethyl but-2-enoate were produced but no base was required for the reaction. The selectivity of the reaction is in the order Cl > Br > I and prop-2-en-1-ol can be successfully carbonylated to prop-2-enyl but-3-enoate by the same system using 3-chloroprop-1-ene as a promoter. 3-Fluoropropene was not carbonylated, but in the presence of H2 underwent hydroformylation to produce acetals. 3-Chlorobut-1-ene and 1-chlorobut-2-ene both produced ethyl pent-3-enoate and 3-ethoxybut-1-ene. In situ and ex situ NMR and IR spectroscopic studies have been used to show that the first step of the reaction is oxidative addition to give [Rh(CH2CH=CH2)Cl2(CO)(PEt3) 2] for which thermodynamic parameters have been obtained. Both 3-chlorobut-1-ene and 1-chlorobut-2-ene give [Rh(CH2CH=CHMe)Cl2-(CO)(PEt3)2] but with different E:Z ratios. The detailed mechanism of the oxidative addition is discussed. The CO inserts into the Rh-C bond to give [Rh(COCH2CH=CH2)Cl2(CO)(PEt3) 2], from which but-3-enoyl chloride reductively eliminates to react with ethanol to give the observed products. High-pressure IR and high-pressure NMR studies reveal that [RhX(CO)(PEt3)2] (X = Cl or Br) reacts with CO to give [RhX(CO)2(PEt3)2], which exists as two isomeric forms. The compound [Rh(OAc)(CO)(PEt3)2] catalyses the formation of prop-2-enyl ethanoate from 1-chloroprop-2-ene and sodium ethanoate. A mechanism is proposed.