558-30-5

Basic information

• Product Name: Isobutylene oxide
• Synonyms: 1,1-Dimethylethylene oxide;1,1-dimethylethyleneoxide;1,2-epoxy-2-methyl-propan;1,2-Isobutylene oxide;1,2-isobutyleneoxide;2,2-dimethyl-oxiran;2-Methyl-1,2-epoxypropane;2-Methyl-1-propene oxide
• CAS NO: 558-30-5
• Molecular Formula: C₄H₈O
• Molecular Weight: 72.11
• EINECS: 209-193-8
• Product Categories: Oxiranes;Simple 3-Membered Ring Compounds
• Mol File: 558-30-5.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 50-51 °C(lit.)
• Flash Point: 33 °F
• Appearance: Clear colorless/Liquid
• Density: 0.812 g/mL at 25 °C(lit.)
• Vapor Pressure: 283mmHg at 25°C
• Refractive Index: n20/D 1.374(lit.)
• Storage Temp.: Flammables area
• Solubility: 58g/l
• Explosive Limit: 1.5-13.5%(V)
• Water Solubility: 58 g/L (20 ºC)
• Sensitive: Moisture Sensitive
• BRN: 102408
• CAS DataBase Reference: Isobutylene oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Isobutylene oxide(558-30-5)
• EPA Substance Registry System: Isobutylene oxide(558-30-5)

Safety Data

• Hazard Codes: F,Xi,Xn,C
• Statements: 11-36/37/38-20/21/22-34
• Safety Statements: 16-26-36-36/37/39-45
• RIDADR: UN 1993 3/PG 1
• WGK Germany: 2
• RTECS: TZ3580000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 558-30-5(Hazardous Substances Data)

Usage

Description

Isobutylene oxide, also known as methyl ethyl epoxy propane, is a colorless liquid with epoxide properties. It is an organic compound that plays a significant role in various chemical reactions and industrial applications due to its unique structure and reactivity.

Uses

Used in Chemical Synthesis:
Isobutylene oxide is used as an initiator in the synthesis of polyisobutylenes. It serves as a starting point for the polymerization process, leading to the formation of polyisobutylene, a versatile polymer with applications in various industries.
Used in the Production of 1-tert-butylperoxy-2-methyl-propan-2-ol:
Isobutylene oxide is also employed as an initiator for the preparation of 1-tert-butylperoxy-2-methyl-propan-2-ol, an important compound used in the production of various chemicals and materials.
Used in the Rubber Industry:
Isobutylene oxide is used as a crosslinking agent in the rubber industry, where it helps improve the mechanical properties and durability of rubber products.
Used in the Pharmaceutical Industry:
Isobutylene oxide is utilized in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapies.
Used in the Coatings Industry:
Isobutylene oxide is used in the production of coatings and adhesives, where it enhances the adhesion properties and durability of the final products.

Flammability and Explosibility

Highlyflammable

InChI:InChI=1/C4H8O/c1-4(2)3-5-4/h3H2,1-2H3

Synthetic route

isobutene (115-11-7) → 2-methyl-1,2-epoxypropane (558-30-5)

Conditions	Yield
With methyltrifluoromethyldioxirane In various solvent(s) for 0.0333333h; other reagent: dimethyldioxirane;	99%
With tert.-butylhydroperoxide; molybdenum(V) chloride In 1,2-dimethoxyethane at 120℃; under 3750.38 Torr; for 4h; Reagent/catalyst; Temperature; Solvent; Pressure; Inert atmosphere;	90%
With DL-dithiothreitol; 1-phenylethyl hydroperoxide; C18H29Cl3NS3Y; molybdenum stearate In ethylbenzene at 150℃; under 37503.8 Torr; for 3.5h; Inert atmosphere;	89.6%

3-chloro-2-methylpropan-2-ol (558-42-9) → 2-methyl-1,2-epoxypropane (558-30-5)

Conditions	Yield
With potassium hydroxide at -15℃; under 500 Torr; for 5h; Epoxidation; Cyclization;	92%
With potassium hydroxide
With sodium hydroxide; water

(C4H9)3SnOC(CH3)2CH2Br → 2-methyl-1,2-epoxypropane (558-30-5) + tributyltin bromide (1461-23-0)

Conditions	Yield
decompn. at 70°C (0.5 h);	A 89% B n/a

(C4H9)3SnOC(CH3)2CH2Cl (35952-62-6) → 2-methyl-1,2-epoxypropane (558-30-5) + tributyltin chloride (1461-22-9)

Conditions	Yield
decompn. at 210°C (1 h);	A 85% B n/a

5-ethyl-2,2-dimethyl-4,6-dioxa-1-aza-bicyclo[3.1.0]hexane (1262887-07-9) + phenylacetylene (536-74-3) → 2-methyl-1,2-epoxypropane (558-30-5) + 3-ethyl-5-phenylisoxazole (4211-90-9)

Conditions	Yield
In toluene for 0.166667h; Reflux; regioselective reaction;	A n/a B 85%

phenylacetylene (536-74-3) + 2,4,4-trimethyloxazoline 2,3-oxide (62539-46-2) → 2-methyl-1,2-epoxypropane (558-30-5) + 3-methyl-5-phenylisoxazole (1008-75-9)

Conditions	Yield
In toluene for 0.166667h; Reflux; regioselective reaction;	A n/a B 85%

bis(triphenylphosphine)-t-butoxy(methyl)nickel (106828-39-1) → 2-methyl-1,2-epoxypropane (558-30-5) + 2-methyl-but-2-ene (513-35-9) + methane (34557-54-5) + isobutene (115-11-7)

Conditions	Yield
In toluene at 50℃; for 12h; Further byproducts given;	A 45% B 16% C 81% D 21%
In toluene at 50℃; for 12h; Further byproducts given;	A 45 % Chromat. B 16 % Chromat. C 81 % Chromat. D 21 % Chromat.

exo-2-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-yl)propan-2-ol (434933-60-5) → 2-methyl-1,2-epoxypropane (558-30-5) + phenanthrene (85-01-8) + 1-methylcyclopropanol (29526-99-6) + butanone (78-93-3)

Conditions	Yield
With Methylenedioxybenzene In benzene-d6 at 20℃; Product distribution; Photolysis;	A 3% B n/a C 28% D 69%

bis(triphenylphosphine)dimethylnickel (91811-93-7) + isopropyl alcohol (67-63-0) → 2-methyl-1,2-epoxypropane (558-30-5) + acetone (67-64-1)

Conditions	Yield
	A 2% B 68%

cis-bis(acetonitrile)chloronitropalladium(II) (91547-45-4) + isobutene (115-11-7) → 2-methyl-1,2-epoxypropane (558-30-5) + (2-methylallyl)palladium-chloride dimer

Conditions	Yield
With oxygen In chloroform-d1 CDCl3, 25°C, 24 h, air;; not sepd., detected by NMR spectra;;	A 16% B n/a

diazomethane (186581-53-3, 908094-01-9) + acetone (67-64-1) → 2-methyl-1,2-epoxypropane (558-30-5)

Conditions	Yield
With 1,1,1-trichloroethanol at 0℃;
With water at 0℃;
With ethanol at 0℃;
With lithium chloride at 0℃;
With formamide at 0℃;

2-chloro-2-methyl-1-propanol (558-38-3) → 2-methyl-1,2-epoxypropane (558-30-5)

Conditions	Yield
With potassium hydroxide

di-tert-butyl peroxide (110-05-4) → 2-methyl-1,2-epoxypropane (558-30-5) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
at 17℃; Photolysis;

di-tert-butyl peroxide (110-05-4) → 2-methyl-1,2-epoxypropane (558-30-5) + methane (34557-54-5) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
at 110℃; Produkt5:Aethan;

di-tert-butyl peroxide (110-05-4) → 2-methyl-1,2-epoxypropane (558-30-5) + ethane (74-84-0) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
at 25 - 79℃; Produkt5-7:Kohlenmonoxid,tert-Butyl-methyl-aether,Methan.Photolysis;

methylene (2465-56-7) + acetone (67-64-1) → 2-methyl-1,2-epoxypropane (558-30-5) + 2,2,4,4-tetramethyl-[1,3]dioxolane (13372-34-4) + 2-Methoxypropene (116-11-0) + butanone (78-93-3)

ethyl N-methyl-N-nitrosocarbamate (615-53-2) + acetone (67-64-1) + butan-1-ol (71-36-3) → 2-methyl-1,2-epoxypropane (558-30-5) + butanone (78-93-3)

Conditions	Yield
With potassium carbonate

isobutene (115-11-7) → 2-methyl-1,2-epoxypropane (558-30-5) + tert-butyl alcohol (75-65-0)

Conditions	Yield
With iodine; potassium iodide

tert.-butylhydroperoxide (75-91-2) → 2-methyl-1,2-epoxypropane (558-30-5) + acetone (67-64-1)

Conditions	Yield
With water Irradiation; addition of t-BuOH, N2O;

tetrachloromethane (56-23-5) + di-tert-butyl peroxide (110-05-4) → 2-methyl-1,2-epoxypropane (558-30-5) + methylene chloride (74-87-3) + hexachloroethane (67-72-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
at 35℃; Product distribution; Mechanism; Irradiation;

Methoxy-(3,4-epoxycyclohexyl)-methyl-tert.-butyl-peroxid (62704-89-6) → 2-methyl-1,2-epoxypropane (558-30-5) + methyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate (41088-52-2) + Methyl formate (107-31-3) + cyclohexane-1,2-epoxide (286-20-4) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
In solid matrix at -196℃; for 10h; Rate constant; Thermodynamic data; Irradiation; activation energy;

tert-butylperoxytrimethylsilane (3965-63-7) → 2-methyl-1,2-epoxypropane (558-30-5) + Trimethylsilanol (1066-40-6) + methane (34557-54-5) + Hexamethyldisiloxane (107-46-0) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
In hexane at 25℃; Product distribution; Kinetics; Irradiation;

Methoxy-tert.-butylperoxycyclohexenylmethan (64651-86-1) → 2-methyl-1,2-epoxypropane (558-30-5) + Methyl formate (107-31-3) + methyl cyclohex-3-ene-1-carboxylate (6493-77-2) + acetone (67-64-1) + tert-butyl alcohol (75-65-0) + cyclohexene (110-83-8)

Conditions	Yield
In solid matrix at -196℃; for 10h; Rate constant; Thermodynamic data; Mechanism; Irradiation; activation energy, other substrates;

vinyltri(tert-butylperoxysilane) (15188-09-7) → 2-methyl-1,2-epoxypropane (558-30-5) + methane (34557-54-5) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
In hexane at 25℃; Product distribution; Kinetics; Heating;

C4H9O2 (274687-62-6) → 2-methyl-1,2-epoxypropane (558-30-5)

Conditions	Yield
Rate constant;

2-tert-butylperoxy-2-methyl-propyl (54156-75-1) → 2-methyl-1,2-epoxypropane (558-30-5) + di-tert-butyl peroxide (110-05-4)

Conditions	Yield
With tri-n-butyl-tin hydride In benzene at 24.9℃; Rate constant; Irradiation;

bis(triphenylphosphine)-t-butoxy(methyl)palladium (106828-10-8) → 2-methyl-1,2-epoxypropane (558-30-5) + 2-methyl-but-2-ene (513-35-9) + methane (34557-54-5) + isobutene (115-11-7)

Conditions	Yield
In toluene 1.) -30 deg C, 2.) raising the temperature to 50 deg C;	A 68 % Chromat. B 4 % Chromat. C 94 % Chromat. D 7 % Chromat.

C41H27(2)H15NiOP2 (106870-87-5) → 2-methyl-1,2-epoxypropane (558-30-5) + methane-d3 (676-80-2) + methane (558-20-3) + isobutene (115-11-7)

Conditions	Yield
In (2)H8-toluene at 50℃; Further byproducts given;	A n/a B 93 % Chromat. C 7 % Chromat. D n/a

3.4-Epoxyhexahydroperbenzoesaeure-tert-butylester (22937-64-0) + 2,2-diphenyl-1-picrylhydrazine (1707-75-1) → 2-methyl-1,2-epoxypropane (558-30-5) + 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl (147506-92-1, 1898-66-4) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
In chlorobenzene at 70℃; Thermodynamic data; Kinetics; Rate constant; E(activ.), ΔS(activ.), oth. solvents, oth. temperature;

Dimethylaminomethyl-tert-butylperoxid (35120-40-2) + 2,2-diphenyl-1-picrylhydrazine (1707-75-1) → 2-methyl-1,2-epoxypropane (558-30-5) + 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl (147506-92-1, 1898-66-4) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
In chlorobenzene at 70℃; Thermodynamic data; Kinetics; Rate constant; E(activ.), ΔS(activ.), oth. solvents, oth. temperature;

2-methyl-1,2-epoxypropane (558-30-5) + dimethyl amine (124-40-3) → 1-dimethylamino-2-methyl-propan-2-ol (14123-48-9)

Conditions	Yield
In water at -5 - 20℃; Schlenk technique; Inert atmosphere; Sealed tube;	100%
With water In water at 20 - 50℃; for 120h; Sealed tube;	91%
In water at 20℃; for 12h; Cooling with ice; Inert atmosphere;	89%

2-methyl-1,2-epoxypropane (558-30-5) + dibenzylamine (103-49-1) → 1-dibenzylamino-2-methyl-propan-2-ol (344868-41-3)

Conditions	Yield
In ethanol at 50℃; for 72h;	100%
With water
With lithium bromide In methanol at 20 - 65℃; for 6h;
With lithium bromide at 20 - 60℃; for 18h;
With lithium bromide at 20 - 60℃; for 18h;

2-methyl-1,2-epoxypropane (558-30-5) + carbon dioxide (124-38-9) → 4,4-dimethyl-1,3-dioxolan-2-one (4437-69-8)

Conditions	Yield
With tetrabutylammomium bromide at 60℃; under 7500.75 Torr; for 72h; Time; Autoclave;	100%
With 2-(bis(5-(tert-butyl)-2-hydroxybenzyl)amino)-N,N,N-trimethylethan-1-aminium iodide at 120℃; Reagent/catalyst; Inert atmosphere; Schlenk technique;	99%
With tetrabutylammomium bromide In neat (no solvent) at 100℃; under 22502.3 Torr; for 8h;	99%

Upstream product

• 186581-53-3 diazomethane 
• 67-64-1 acetone 
• 558-42-9 3-chloro-2-methylpropan-2-ol 
• 558-38-3 2-chloro-2-methyl-1-propanol 
• 2465-56-7 methylene 
• 56-23-5 tetrachloromethane 
• 110-05-4 di-tert-butyl peroxide 
• 274687-62-6 C₄H₉O₂ 
• 115-11-7 isobutene 
• 75-65-0 tert-butyl alcohol 
• 3972-25-6 tert-butyl alcohol-d 
• 26482-65-5 2,2-dimethyl-1,3-propanediol dinitrate 
• 123-72-8 butyraldehyde 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 13150-40-8 2-methyl-1-(piperidin-1-yl)propan-2-ol 
• 156339-46-7 3-(piperazin-1-yl)-2-methylpropan-2-ol 
• 3587-64-2 1-Methoxy-2-methylpropan-2-ol 
• 22665-67-4 2-methoxyisobutanol 
• 590-36-3 2-methylpentan-2-ol 
• 598-75-4 3-methyl-2-butanol 
• 59909-84-1 α-cyano-γ,γ-dimethyl-γ-butyrolactone 
• 856978-60-4 (2,4-dinitro-phenylsulfanyl)-tert-butyl alcohol 
• 3587-69-7 1-butoxy-2-methyl-propan-2-ol 
• 600-36-2 2,4-dimethyl-3-pentanol 
• 617-29-8 2-methylhexan-3-ol 
• 3772-13-2 2,2-dimethylthiirane 
• 75-85-4 tert-Amyl alcohol 
• 625-23-0 2-methylhexan-2-ol 

Relevant articles and documents

-

-

Dioxirane epoxidations of 1,1-disubstituted ethylenes. Probing for radical pathways by computations and experiments

-

PROCESS AND SYSTEM TO MAKE SUBSTITUTED LACTONES

A process for oxidizing iso-butane with oxygen to produce t-butyl hydroperoxide and t-butyl alcohol; dehydrating at least a portion of the t-butyl alcohol to produce di-tert-butyl ether and isobutylene; epoxidizing at least a portion of the isobutylene with the t-butyl hydroperoxide to produce isobutylene oxide and t-butyl alcohol; and carbonylating at least a portion of the isobutylene oxide with carbon monoxide to produce pivalolactone.

Synthesis and Structure of Tin and Germanium Complexes as Precursors Containing Alkoxyaminoalkoxide Ligands for Thin Film Transistors

This paper describes the preparation of four novel Sn and Ge complexes containing alkoxyaminoalkoxide type ligands {L1H = 1-[methoxy(methyl)amino]-2-methylpropan-2-ol; L2H = 1-[methoxy(methyl)amino]-2-methylbutan-2-ol} for potential use as precursors for thin film transistors. All compounds were prepared at room temperature by stirring a solution containing Sn(btsa)2 [btsa = bis(trimethylsilyl)amide] or Ge(btsa)2 with two equivalents of L1H or L2H to form Sn(L1)2 (1), Sn(L2)2 (2), Ge(L1)2 (3) and Ge(L2)2 (4). All of the complexes were characterized by NMR and FTIR spectroscopy as well as elemental and thermogravimetric analyses. When the more symmetric and compact ligand L1H was applied, solid products 1 and 3 were generated and their structures were studied using X-ray diffraction. Applying the strategy of ligand design at the molecular level, the symmetric ligand was changed to an asymmetric one, replacing one of the two neighboring methyl groups of the amino alcohol group with an ethyl group, and forming liquid complexes 2 and 4 for both metals.

Method for synthesizing isovaleraldehyde

The invention provides a synthetic method of 3-methylcrotonaldehyde. The method comprises the following steps that epoxy isobutane is subjected to a hydroformylation reaction, hydroxy isovaleraldehydeis obtained, hydroxy isovaleraldehyde is subjected to an intramolecular dehydration reaction, and 3-methylcrotonaldehyde is obtained. The synthetic method of 3-methylcrotonaldehyde does not need harsh reaction conditions.