4188-71-0

Basic information

• Product Name: tert-butyl (1Z)-prop-1-en-1-yl ether
• Synonyms: cis-1-Propenyl tert-butyl ether
• CAS NO: 4188-71-0
• Molecular Formula: C₇H₁₄O
• Molecular Weight: 114.1855
• Mol File: 4188-71-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 111.4°C at 760 mmHg
• Density: 0.792g/cm³
• Vapor Pressure: 26.8mmHg at 25°C
• Refractive Index: 1.417
• CAS DataBase Reference: tert-butyl (1Z)-prop-1-en-1-yl ether(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (1Z)-prop-1-en-1-yl ether(4188-71-0)
• EPA Substance Registry System: tert-butyl (1Z)-prop-1-en-1-yl ether(4188-71-0)

Safety Data

• Hazardous Substances Data: 4188-71-0(Hazardous Substances Data)

Upstream product

• 557-40-4 Allyl ether 
• 2259-30-5 tert-butylmagnesium bromide 
• 1471-04-1 allyl tert-butyl ether 

Downstream Products

• 1471-04-1 allyl tert-butyl ether 
• 1132679-97-0 methyl 2-(3,5-dimethoxybenzamido)-3-tert-butoxy-2-phenylpentanoate 

Relevant articles and documents

An isomerization-1,3-dipolar cycloaddition tandem reaction towards the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines from O-allyl compounds

A new strategy for the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines via tandem catalytic isomerization of O-allyl systems to O-(1-propenyl) systems-1,3-dipolar cycloaddition (1,3-DC) to nitrile oxides is presented. The influence of the heteroatom in Ph-X-CH=CHCH3 (X=O, S, or Se) on the regio- and stereoselectivity of ArCNO 1,3-cycloaddition to these dipolarophiles is analyzed as well. The dipolarophiles were obtained via [RuClH(CO)(PPh3)3]-, [RuH2(CO)(PPh 3)]- or base (KOH/18-crown-6)-catalyzed double bond migration in corresponding allyl ethers, O-allyl acetals, PhS- and PhSe-allyl systems. Cycloadditions of nitrile oxides to O-(1-propenyl) systems were fully regioselective whereas in the reactions of ArCNO with the PhS-(1-propenyl) and PhSe-(1-propenyl) systems both possible regioisomers were formed. It was established that within the majority of dipolarophiles of ROCHCHCH3 type 1,3-DC is concerted, while for some dipolarophiles of RXCH=CHCH3 (X=O and R=Ph3C, 2,3-dihydroxypropyl, tetrahydropyran-2-yl; X=S or Se and R=Ph) type 1,3-DC turns into a two-step reaction with simultaneous rotation about C-C bond. The results of the experiments have been analyzed theoretically using DFT calculations. The results of these calculations agreed well with the experimental data.

Relative Thermodynamic Stabilities of Isomeric Alkyl Allyl and Alkyl (Z)-Propenyl Ethers

The relative thermodynamic stabilities of ten allyl ethers (ROCH2CH=CH2) and the corresponding isomeric (Z)-propenyl ethers (where R is an alkyl group, or a methoxysubstituted alkyl group) have been determined by chemical equilibration in DMSO solution with t-BuOK as catalyst.From the variation of the equilibrium constant with temperature, the values of the thermodynamic parameters ΔG, ΔH and ΔS of isomerization at 298.15 K were evaluated.The propenyl ethers are highly favored at equilibrium, the values of both ΔG and ΔH for the allyl -> propenyl reaction being ca. -18 to 25 kJ mol-1.The favor of the propenyl ethers is increased by bulky alkyl substituents, and decreased by methoxysubstituted alkyl groups.In most cases the entropy contribution is negligible; however, for R=(MeO)2CH and R=(MeO)3C the values of ΔS are ca. -5 J K-1 mol1-.