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

Chemical Properties

clear colorless liquid

Uses

Different sources of media describe the Uses of 558-30-5 differently. You can refer to the following data:
1. Isobutylene oxide is an epoxide that is used as an initiator in the synthesis of polyisobutylenes.
2. Isobutylene oxide is employed as an initiator for the preparation of polyisobutylenes. It finds application in the synthesis of 1-tert-butylperoxy-2-methyl-propan-2-ol.

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

• 558-42-9 3-chloro-2-methylpropan-2-ol 
• 615-53-2 ethyl N-methyl-N-nitrosocarbamate 
• 67-64-1 acetone 
• 71-36-3 butan-1-ol 
• 115-11-7 isobutene 
• 15464-00-3 azobisisopropane 
• 15464-01-4 azo-t-butane 
• 98-83-9 isopropenylbenzene 
• 75-65-0 tert-butyl alcohol 
• 3972-25-6 tert-butyl alcohol-d 
• 26482-65-5 2,2-dimethyl-1,3-propanediol dinitrate 
• 91547-45-4 cis-bis(acetonitrile)chloronitropalladium(II) 
• 1262887-07-9 5-ethyl-2,2-dimethyl-4,6-dioxa-1-aza-bicyclo[3.1.0]hexane 
• 536-74-3 phenylacetylene 

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

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

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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.

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.

PROCESS FOR PREPARING 3-HYDROXY-3-METHYLBUTYRATE (HMB) AND SALTS THEREOF

The present invention pertains to a process for preparing 3-hydroxy-3-methylbutyrate (HMB) or a salt thereof, the method comprising (a) reacting isobutylene oxide with cyanide in order to obtain 3- hydroxy-3-methylbutyronitrile, and (b) hydrolyzing the 3-hydroxy-3-methylbutyronitrile obtained in step (a) in order to obtain HMB, wherein hydrolysis step (b) is performed using either at least one nitrilase enzyme or, alternatively, using a combination of enzymes, said combination comprising at least one nitrile hydratase and at least one amidase.