23850-78-4

Basic information

• Product Name: isobutyloxirane
• Synonyms: isobutyloxirane;(2-Methylpropyl)oxirane;1,2-Epoxy-4-methylpentane;Nsc92739;Oxirane, (2-methylpropyl)-;Pentane, 1,2-epoxy-4-methyl-;2-isobutyloxirane
• CAS NO: 23850-78-4
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.15888
• EINECS: 245-911-6
• Mol File: 23850-78-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 103.9°Cat760mmHg
• Flash Point: 9.5°C
• Appearance: /
• Density: 0.869g/cm³
• Vapor Pressure: 36.6mmHg at 25°C
• Refractive Index: 1.423
• CAS DataBase Reference: isobutyloxirane(CAS DataBase Reference)
• NIST Chemistry Reference: isobutyloxirane(23850-78-4)
• EPA Substance Registry System: isobutyloxirane(23850-78-4)

Safety Data

• Hazardous Substances Data: 23850-78-4(Hazardous Substances Data)

Usage

Description

Isobutyloxirane, also known as 2-methyl-2,3-epoxybutane, is a colorless liquid chemical compound with the formula C5H10O and a slightly fruity odor. It is recognized for its use as a solvent and as a precursor in the synthesis of various other chemicals, including pharmaceuticals, pesticides, and other organic compounds. Due to its hazardous nature, isobutyloxirane requires careful handling and appropriate safety measures.

Uses

Used in Chemical Synthesis:
Isobutyloxirane is used as a precursor in the chemical synthesis process for the production of a variety of organic compounds. Its reactivity and functional group make it a valuable intermediate in the creation of new chemical entities.
Used in Pharmaceutical Production:
In the pharmaceutical industry, isobutyloxirane is utilized as a building block for the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties.
Used in Pesticide Formulation:
Isobutyloxirane is employed in the formulation of pesticides, where it serves as a key component in the creation of effective and targeted pest control agents. Its chemical properties contribute to the stability and performance of these products.
Used as a Solvent:
Isobutyloxirane is used as a solvent in various industrial applications due to its ability to dissolve a wide range of substances. Its solvent properties are beneficial in processes that require the dissolution of specific compounds for further reactions or applications.
Safety Precautions:
Given its classification as a hazardous chemical, isobutyloxirane necessitates adherence to proper safety protocols during its handling, storage, and use. This includes the use of personal protective equipment, containment measures, and adherence to regulatory guidelines to minimize risks associated with its use.

InChI:InChI=1/C6H12O/c1-5(2)3-6-4-7-6/h5-6H,3-4H2,1-2H3

Upstream product

• 84055-72-1 4-methyl-1-chloro-2-pentanol 
• 691-37-2 4-Methyl-1-pentene 
• 87760-51-8 4-methylpentane-1,2-diol 

Downstream Products

• 108-11-2 Methyl isobutyl carbinol 
• 626-89-1 4-Methyl-1-pentanol 
• 135574-63-9 penaresidin B 
• 14314-21-7 (+/-)-ipsenol 
• 111221-88-6 Toluene-4-sulfonic acid 1-hydroxymethyl-3-methyl-butyl ester 
• 111221-87-5 2-hydroxy-4-methylpentyl-p-toluenesulfonate 
• 83022-91-7 4-Methyl-1-(1-phenylsulfanyl-cyclopropyl)-pentan-2-ol 
• 144343-12-4 2-isobutylcyclopropyl phenyl sulfone 

Relevant articles and documents

Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides

The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.

Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene

Alkenyl boronic esters are important reagents in organic synthesis. Herein, we report that these valuable products can be accessed by the homologation of boronic esters with lithiated epoxysilanes. Aliphatic and electron-rich aromatic boronic esters provided vinylidene boronic esters in moderate to high yields, while electron-deficient aromatic and vinyl boronic esters were found to give the corresponding vinyl silane products. Through DFT calculations, this divergence in mechanistic pathway has been rationalized by considering the stabilization of negative charge in the C?Si and C?B bond breaking transition states. This vinylidene homologation was used in a short six-step stereoselective synthesis of the proposed structure of machillene, however, synthetic and reported data were found to be inconsistent.

Regioselectivity and diasteroselectivity in Pt(II)-mediated "green" catalytic epoxidation of terminal alkenes with hydrogen peroxide: Mechanistic insight into a peculiar substrate selectivity

Recently developed electron-poor Pt(II) catalyst 1 with the "green" oxidant 35% hydrogen peroxide displays high activity and complete substrate selectivity in the epoxidation of terminal alkenes because of stringent steric and electronic requirements. In the presence of isolated dienes bearing terminal and internal double bonds, epoxidation is completely regioselective toward the production of terminal epoxides. Insight into the mechanism is gained by means of a reaction progress kinetic analysis approach that underlines the peculiar role of 1 in activating both the alkene and H 2O2 in the rate-determining step providing a rare example of nucleophilic oxidation of alkenes by H2O2.