2167-39-7

Basic information

• Product Name: 1,3-Epoxybutane
• Synonyms: 1,3-Epoxybutane;2-Methyloxetane
• CAS NO: 2167-39-7
• Molecular Formula: C₄H₈O
• Molecular Weight: 72.1057
• Mol File: 2167-39-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 60 °C
• Boiling Point: 59°C (estimate)
• Appearance: /
• Density: 0.8410
• Vapor Pressure: 217mmHg at 25°C
• Refractive Index: 1.3885
• CAS DataBase Reference: 1,3-Epoxybutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Epoxybutane(2167-39-7)
• EPA Substance Registry System: 1,3-Epoxybutane(2167-39-7)

Safety Data

• Hazardous Substances Data: 2167-39-7(Hazardous Substances Data)

Usage

Description

1,3-Epoxybutane, also known as 1,3-oxetane, is a cyclic ether with the molecular formula C4H8O. It is a colorless, volatile liquid with a characteristic ether-like odor. The presence of the epoxy group in its structure makes it a versatile compound with unique chemical properties.

Uses

Used in Medicinal Chemistry:
1,3-Epoxybutane is used as a stable motif for its influence on the physicochemical properties of various compounds in medicinal chemistry. Its unique structure allows it to form stable derivatives with potential applications in drug development.
Used as a Synthetic Intermediate:
1,3-Epoxybutane is used as a synthetic intermediate for its propensity to undergo ring-opening reactions. This property makes it a valuable building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Polymer Synthesis:
1,3-Epoxybutane is used as a monomer in the synthesis of polymers, such as polyethers and epoxy resins. These polymers have a wide range of applications, including coatings, adhesives, and composite materials.
Used in Chemical Synthesis:
1,3-Epoxybutane is used as a reagent in various chemical synthesis processes, such as the preparation of alcohols, ketones, and other organic compounds. Its ability to participate in a variety of reactions makes it a useful tool in organic chemistry.

InChI:InChI=1/C4H8O/c1-4-2-3-5-4/h4H,2-3H2,1H3

Upstream product

• 503-30-0 trimethylene oxide 
• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 463-51-4 Ketene 
• 40894-09-5 <3-Brom-1-methyl-propoxy-(1)>-tributyl-zinn 
• 2203-34-1 4-chloro-2-butanol 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 1679-47-6 3-methyltetrahydro-2-furanone 

Downstream Products

• 4737-47-7 ethyl-2 oxetanne 
• 6245-99-4 2,2-dimethyl-oxetane 
• 13423-15-9 3-methyltetrahydrofuran 
• 14988-66-0 2,4-dimethyl-oxetane 
• 96-47-9 2-methyltetrahydrofuran 
• 22983-43-3 2,3-dimethyloxetane 
• 10034-14-7 trans-1-methoxy-2-butene 
• 4696-30-4 methoxy-1 butene-3 
• 10034-16-9 (Z)-1-Methoxy-2-buten 
• 22983-43-3 2,3-dimethyloxetane 
• 17361-58-9 4-methyl-[1,3]dioxan-2-one 
• 117901-61-8 1-phenylselenobutan-3-ol 
• 99855-05-7 6-methyl-3-phenyl-1,3-oxazinan-2-one 
• 187737-37-7 propene 

Relevant articles and documents

The reactions of 4-chloro-2-butanol and 3-chloro-1-butanol with aqueous sodium hydroxide, and 1-chloro-2-propanol and 2-chloro-1-propanol with isopropyl amine

The total reaction of 4-chloro-2-butanol 1 with NaOH(aq) is dominated (74%) by intramolecular substitution (SNi), besides which bimolecular substitution (SN2, 12%) and 1,4-elimination (i.e. fragmentation, contrary to earlier arguments) exhibit a significant contribution (11%). The total reaction of 3-chloro-1-butanol 2 instead is dominated by 1,4-(72%) and 1,2-elimination (25%), the substitution reactions being just observable (SNi 2% and SN2 1%). In 1 both the +I-effect and the conformational factors in the intermediate γ-chloroalkoxy anion favour the SNi-reaction, whereas in 2 the situation is opposite and the location of Cl on a secondary carbon also makes the SNi-reaction less favourable. The relative proportions of 1,4-and 1,2-eliminations for 2 can be explained by thermodynamic basis since the consequent products are more stable than the corresponding products from 1. 1-chloro-2-propanol 3 and 2-chloro-1-propanol 4 both react with isopropyl amine giving the same product, namely 1-isopropylamino-2-propanol, which indicates that the reaction proceeds through the propylene oxide intermediate. Compound 1 also reacted with isopropyl amine predominantly via SNi-reaction, giving first 2-methyloxetane which then further gave 4-isopropylamino-2-butanol, whereas 2 gave 3-isopropylamino-1-butanol through a direct S N2-reaction. ARKAT-USA, Inc.

OXYGEN YLIDES-I. REACTIONS OF CARBENES WITH OXETANE

The ylides generated from carbenes (:CH2, :CHCO2Et, :CHPh) and oxetane in the presence of methanol undergo Stevens rearrangement and protonation competitively, yielding tetrahydrofurans and 1,3-dialkoxycyclopropanes as major products.