buta-1,3-diene
A
epoxybutene
B
1,2:3,4-Diepoxybutane
Conditions | Yield |
---|---|
Stage #1: With sodium oxalate; oxalic acid; manganese(II) acetate; N,N',N''-trimethyl-1,4,7-triazacyclononane In water Stage #2: buta-1,3-diene With dihydrogen peroxide In water at -40 - 25℃; under 2400.24 - 3900.39 Torr; for 8.5h; Cooling with acetone-dry ice; | A n/a B 95.5% |
Conditions | Yield |
---|---|
With [N,N'-bis(salicylidene)-1,2-ethanediaminato]Mn(III) chloride; iodosylbenzene In dichloromethane | 92% |
With dihydrogen peroxide; teterabutylammonium In acetonitrile at 31.85℃; for 9h; | 91% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 45℃; for 48h; |
(2-bromoethyl)oxirane
sodium diethylmalonate
ethanol
epoxybutene
Conditions | Yield |
---|---|
bei Raumtemperatur in 35 min; |
Conditions | Yield |
---|---|
at 17 - 18℃; Geschwindigkeit; |
Conditions | Yield |
---|---|
With ethyl acetate | |
With acetone |
Conditions | Yield |
---|---|
With chloroethane |
Conditions | Yield |
---|---|
With diethyl ether |
1,4-dichloro-2-butene
A
epoxybutene
B
1-chloroprene
C
1,4-butenediol
D
acetaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N-dodecyl-N,N-bis(beta-hydroxyethyl)ammonium chloride at 60 - 90℃; Product distribution; Kinetics; Thermodynamic data; further catalyst and base; E(excit.); |
Conditions | Yield |
---|---|
With diethoxyltriphenylphosphorane In chloroform-d1 at 61℃; for 18h; Yield given; |
(2E)-4-bromobut-2-en-1-yl acetate
epoxybutene
Conditions | Yield |
---|---|
With potassium hydroxide at 60 - 80℃; for 0.333333h; Yield given; | |
With potassium hydroxide Yield given; |
(E)-1-chloro-4-acetoxybut-2-ene
epoxybutene
Conditions | Yield |
---|---|
With potassium hydroxide at 60 - 80℃; for 0.333333h; Yield given; | |
With potassium hydroxide |
epoxybutene
Conditions | Yield |
---|---|
With sodium hydroxide at 90℃; |
buta-1,3-diene
A
epoxybutene
B
3-butenal
C
nitrogen(II) oxide
Conditions | Yield |
---|---|
With Nitrogen dioxide In solid matrix Mechanism; Rate constant; Irradiation; Ar matrix; |
1,2:3,4-Diepoxybutane
epoxybutene
Conditions | Yield |
---|---|
With B single-collision conditions; |
Conditions | Yield |
---|---|
With molybdenum propylene glycolate at 80℃; kinetic studies; var. conc. of peroxide and molybdenum glycolate; |
Conditions | Yield |
---|---|
With Nitrogen dioxide; dinitrogen pentoxide; nitrate radical at 298℃; under 740 Torr; Product distribution; Further Variations:; Reagents; Oxidation; Nitration; Photolysis; |
epoxybutene
Conditions | Yield |
---|---|
With sodium hydroxide | |
With potassium hydroxide |
epoxybutene
Conditions | Yield |
---|---|
With sodium hydroxide | |
With potassium hydroxide |
epoxybutene
Conditions | Yield |
---|---|
With hydrogen bromide Behandeln des Reaktionsprodukts mit Kaliumhydroxid; |
epoxybutene
Conditions | Yield |
---|---|
With sodium hydroxide |
epoxybutene
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
at 100℃; |
1-chloro-2-hydroxy-3-butene
A
epoxybutene
B
3,4-butenediol
C
(E)-2-butene-1,4-diol
buta-1,3-diene
A
epoxybutene
B
furan
C
carbon dioxide
D
crotonaldehyde
Conditions | Yield |
---|---|
With oxygen; aluminum oxide; silver at 270℃; Product distribution; Further Variations:; butadiens: 2,3-d2; 1,1,4,4-d4; d6; |
Conditions | Yield |
---|---|
With aluminium(III) triflate at 100℃; for 1h; regioselective reaction; | 100% |
Stage #1: epoxybutene; methanol at 0℃; for 0.5h; Stage #2: With sulfuric acid at 0 - 20℃; for 3h; | 25% |
With boron trifluoride diethyl etherate |
epoxybutene
piperidine-2,6-dione
1-[(1R)-1-(hydroxymethyl)-2-propenyl]-2,6-piperidinedinone
Conditions | Yield |
---|---|
Stage #1: piperidine-2,6-dione With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate In dichloromethane at 20℃; for 1.16667h; Inert atmosphere; Stage #2: epoxybutene In dichloromethane at 20℃; for 14h; Inert atmosphere; optical yield given as %ee; regioselective reaction; | 100% |
epoxybutene
4-((2-hydroxybut-3-enyl)thiomethyl)-4-methyloxazolidin-2-one
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 14h; | 100% |
epoxybutene
di-tert-butyl dicarbonate
1-amino-2-propene
N-allyl-N-(2-hydroxy-but-3-enyl)-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: epoxybutene; 1-amino-2-propene In water at 80℃; for 6h; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In 1,4-dioxane; water at 20℃; | 100% |
Stage #1: epoxybutene; 1-amino-2-propene In water at 100℃; for 6h; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In 1,4-dioxane; water at 20℃; for 12h; | 56% |
Conditions | Yield |
---|---|
Stage #1: epoxybutene; 2-methylallylamin In water at 80℃; for 6h; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In 1,4-dioxane; water at 20℃; | 100% |
epoxybutene
chloro-trimethyl-silane
(1-Chloromethyl-allyloxy)-trimethyl-silane
Conditions | Yield |
---|---|
triphenylphosphine In chloroform at -50℃; for 0.25h; | 99% |
epoxybutene
N-(4-methylbenzylidene)-p-toluenesulfonamide
Conditions | Yield |
---|---|
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 4h; Ambient temperature; | 99% |
epoxybutene
(E)-N-4-methylbenzylidene-4-toluenesulfonamide
Conditions | Yield |
---|---|
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 4h; Cycloaddition; | 99% |
epoxybutene
benzyl chloroformate
((E)-4-hydroxy-but-2-enyl)-carbamic acid benzyl ester
Conditions | Yield |
---|---|
Stage #1: epoxybutene In benzene-d6 at 23℃; Stage #2: benzyl chloroformate With potassium carbonate In tetrahydrofuran; benzene-d6 at 23℃; for 12h; Further stages.; | 99% |
epoxybutene
Conditions | Yield |
---|---|
C64H74Cl2Co2N4O4; bis(triphenylphosphoranylidene)-ammonium acetate In toluene at 0℃; for 21h; | 99% |
epoxybutene
phthalimide
(+)-2-[(1R)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate optical yield given as %ee; | 99% |
With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate optical yield given as %ee; enantioselective reaction; | 99% |
Stage #1: phthalimide With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: epoxybutene In dichloromethane at 20℃; for 14h; Inert atmosphere; | 99% |
Stage #1: phthalimide With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: epoxybutene In dichloromethane at 20℃; for 12h; Inert atmosphere; | 97% |
With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate In dichloromethane at 20℃; Inert atmosphere; enantioselective reaction; | 92% |
Conditions | Yield |
---|---|
Stage #1: tert-butyl N-(trifluoroacetyl)glycinate With zinc(II) chloride; lithium hexamethyldisilazane Inert atmosphere; Stage #2: epoxybutene With bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); (4R,5R)-2-((S)-1-(2-(dibutylphosphino)naphthalen-1-yl)naphthalen-2-yl)-4,5-diphenyl-1-tosyl-4,5-dihydro-1H-imidazole In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; Schlenk technique; | 99% |
epoxybutene
(E)-1-phenyl-2-buten-1-one
Conditions | Yield |
---|---|
With 5,5’-bis(diphenylphosphino)-2,2,2’,2’-tetrafluoro-4,4’-bi-1,3-benzodioxole; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In 1,4-dioxane at 15℃; for 120h; Inert atmosphere; Sealed tube; stereoselective reaction; | 99% |
Conditions | Yield |
---|---|
With lithium phosphate In hexane at 310℃; Isomerization; | 98.9% |
epoxybutene
3-Methyl-2-butenyl-trimethylstannane
3,3-Dimethyl-2-vinyl-pent-4-en-1-ol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -78℃; for 0.5h; | 98% |
epoxybutene
1,3-Diphenylcarbodiimide
N-phenyl-3-phenyl-4-vinyl-1,3-oxazolidin-2-imine
Conditions | Yield |
---|---|
With triphenylphosphine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 15h; Ambient temperature; | 98% |
tetraphenyl stibonium iodide In benzene at 40℃; for 29h; | 62% |
With (R)-C1-TunePhos; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 20℃; Product distribution; Further Variations:; Reagents; |
epoxybutene
phthalimide
(-)-2-[(1S)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); R,R-C52H44N2O2P2 chiral ligand; sodium carbonate In dichloromethane for 14h; Ambient temperature; | 98% |
With sodium carbonate; (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl); bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 20℃; for 14h; ring cleavage; | 98% |
With bis(η3-allyl-μ-chloropalladium(II)); sodium carbonate; (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl) In dichloromethane at 20℃; for 22h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 98% |
epoxybutene
p-chlorphenylisocyanate
3-(4-chlorophenyl)-4-vinyloxazolidin-2-one
Conditions | Yield |
---|---|
With triphenylphosphine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 15h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
at 130 - 140℃; under 760.051 Torr; | 98% |
at 120 - 140℃; under 760.051 Torr; | 98% |
at 130℃; under 760.051 Torr; | 98% |
epoxybutene
dimethyl allylmalonate
dimethyl allyl(4-hydroxy-2E-butenyl)malonate
Conditions | Yield |
---|---|
With Pd2(dba)4; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 20℃; for 3h; | 98% |
epoxybutene
1-hydroxy-2-iodo-3-butene
Conditions | Yield |
---|---|
With water; hydrogen iodide at 0℃; for 0.166667h; Darkness; | 98% |
Conditions | Yield |
---|---|
With 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 20℃; for 5h; | 98% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); (E)-N-cyclohexyl-1-(2-(diphenylphosphanyl)phenyl)methanimine In toluene at 30℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With 1-methyl-3-(3-phenylthioureido)pyridinium iodide; tetra-(n-butyl)ammonium iodide at 60℃; Sealed tube; | 97% |
With dmap; C40H49AlN4O4S2 at 20 - 120℃; under 750.075 Torr; for 8h; Catalytic behavior; Autoclave; | 97% |
With calcium iodide In neat (no solvent) at 25℃; under 7500.75 Torr; for 24h; | 95% |
Conditions | Yield |
---|---|
With lithium chloride; copper dichloride; palladium dichloride In tetrahydrofuran; water 0 deg C, 10-12 h then 25 deg C, 2-3 h; | 97% |
Conditions | Yield |
---|---|
With carbon monoxide; tetrabutylammomium bromide; water; triethylamine; dodecacarbonyl-triangulo-triruthenium In 1,4-dioxane at 75℃; under 2068.65 Torr; for 20h; Product distribution / selectivity; Autoclave; | 97% |
With rhodium(III) chloride hydrate; carbon monoxide; tetrabutyl-ammonium chloride; water; triethylamine In 1,4-dioxane at 75℃; under 2068.65 Torr; for 24h; Reagent/catalyst; Inert atmosphere; diastereoselective reaction; | 88% |
epoxybutene
1-phenylethenylmagnesium bromide
(E)-5-phenyl-hexa-2,5-dien-1-ol
Conditions | Yield |
---|---|
With copper(l) cyanide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In acetonitrile at 40℃; for 7h; Inert atmosphere; diastereoselective reaction; | 97% |
epoxybutene
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tetrabutylammomium bromide; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane at 20℃; for 6h; Inert atmosphere; Schlenk technique; diastereoselective reaction; | 97% |
Reported in EPA TSCA Inventory.
The 3,4-Epoxy-1-butene, with the CAS registry number 930-22-3, is also known as Butadiene monoepoxide. It belongs to the product categories of Oxiranes; Simple 3-Membered Ring Compounds. Its EINECS number is 213-210-4. This chemical's molecular formula is C4H6O and molecular weight is 70.09. What's more, its systematic name is 2-Vinyloxirane. Its classification codes are: (1)Mutagens; (2)Mutation data; (3)Noxae; (4)Tumor data. This chemical is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides, heat and water.
Physical properties of 3,4-Epoxy-1-butene are: (1)ACD/LogP: 0.192; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.19; (4)ACD/LogD (pH 7.4): 0.19; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 30.30; (8)ACD/KOC (pH 7.4): 30.30; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 12.53 Å2; (13)Index of Refraction: 1.578; (14)Molar Refractivity: 21.609 cm3; (15)Molar Volume: 65.141 cm3; (16)Polarizability: 8.566×10-24cm3; (17)Surface Tension: 35.9 dyne/cm; (18)Density: 1.076 g/cm3; (19)Flash Point: -50 °C; (20)Enthalpy of Vaporization: 29.867 kJ/mol; (21)Boiling Point: 70 °C at 760 mmHg; (22)Vapour Pressure: 142.6 mmHg at 25°C.
Preparation: this chemical can be prepared by buta-1,3-diene at the ambient temperature. This reaction will need reagent NaOCl and solvents CH2Cl2, H2O with the reaction time of 24 hours. The yield is about 92%.
Uses of 3,4-Epoxy-1-butene: it can be used to produce 1,2-dibromo-3,4-epoxy-butane at the temperature of 0 °C. It will need reagent Br2 and solvent CH2Cl2 with the reaction time of 3 hours. The yield is about 65%.
When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable. It is irritating to eyes and it is harmful if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and gloves.
You can still convert the following datas into molecular structure:
(1)SMILES: O1C(\C=C)C1
(2)Std. InChI: InChI=1S/C4H6O/c1-2-4-3-5-4/h2,4H,1,3H2
(3)Std. InChIKey: GXBYFVGCMPJVJX-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | intraperitoneal | 168mg/kg (168mg/kg) | Toxicology and Applied Pharmacology. Vol. 52, Pg. 422, 1980. |
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