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

General Description

(2E)-1-ethoxybut-2-ene is a chemical compound with the molecular formula C6H12O. It is also known by the names (E)-1-Ethoxy-2-butene and Ethyl vinyl ether. It is a colorless liquid with a sweet, fruity odor. It is commonly used as a solvent or as an intermediate in the production of other chemicals. It can undergo polymerization or be used in reactions such as the Wittig reaction to form different compounds. Its structure includes a butene chain with an ethoxy group attached to the second carbon atom, and it has a cis configuration at the double bond. It is important to handle this compound with care as it can be a flammable and hazardous substance if not properly handled.

Upstream product

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

Downstream Products

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

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.