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

Uses

2-Methyloxetane is a derivative of oxetane which has been increasingly exploited for its contrasting behaviours; such as its influence on physicochemistry properties as a stable motif in medicinal chemistry and its propensity to undergo ring-opening reactions as a synthetic intermediate.

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 
• 1679-47-6 3-methyltetrahydro-2-furanone 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 40894-09-5 <3-Brom-1-methyl-propoxy-(1)>-tributyl-zinn 
• 2203-34-1 4-chloro-2-butanol 

Downstream Products

• 50551-88-7 5-methylhex-5-en-2-ol 
• 4630-06-2 6-methylhept-5-en-2-ol 
• 39177-79-2 Diphenyl-(1-methyl-3-chlorpropyl)-phosphit 
• 2344-71-0 5-phenylpentan-2-ol 
• 2344-70-9 1-phenyl-3-butanol 
• 24395-10-6 6-heptene-2-ol 
• 1190-22-3 1,3-dichlorobutane 
• 78-92-2 iso-butanol 
• 50-00-0 formaldehyd 
• 187737-37-7 propene 
• 74-85-1 ethene 
• 75-07-0 acetaldehyde 
• 1047661-69-7 N-(4-hydroxy-1-phenylpentyl)benzenecarbothioamide 
• 53044-15-8 3-(Trimethylstannyl)-2-butanol 

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.