Conditions | Yield |
---|---|
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 120℃; | 97% |
With potassium hydroxide at 220℃; |
Conditions | Yield |
---|---|
With quinoline at 30 - 105℃; under 12751.3 Torr; Temperature; Pyrolysis; | 93.6% |
With quinoline; toluene-4-sulfonic acid at 90℃; for 9h; Catalytic behavior; Reagent/catalyst; Temperature; | 92.8% |
With (trimethylsilyl)manganese pentacarbonyl In acetonitrile at 50℃; for 2h; Mechanism; | 77 % Spectr. |
carbon dioxide
2,2-dimethoxy-propane
A
2-Methoxypropene
B
acetone
C
carbonic acid dimethyl ester
Conditions | Yield |
---|---|
With dibutyldimethoxytin at 180℃; under 1520000 Torr; for 24h; Product distribution; metal-catalyzed reaction of acetals with CO2; effect of catalyst structure; effect of additives; pressure effect; possible mechanism; | A n/a B 85% C 88% |
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium tert-butylate In methanol | 60% |
In methanol | 47% |
methylene
acetone
A
2-methyl-1,2-epoxypropane
B
2,2,4,4-tetramethyl-[1,3]dioxolane
C
2-Methoxypropene
D
butanone
pyridine
t-butyl heptafluoroperoxybutyrate
A
2-Methoxypropene
B
tert-butyl heptafluorobutyrate
C
pyridinium heptafluorobutyrate
D
1,1'-(1,2-ethanediyl)bisbenzene
Conditions | Yield |
---|---|
In toluene at 85℃; for 7h; Yield given. Further byproducts given. Yields of byproduct given; |
pyridine
t-butyl heptafluoroperoxybutyrate
A
2-Methoxypropene
B
tert-butyl heptafluorobutyrate
C
pyridinium heptafluorobutyrate
D
1,1'-(1,2-ethanediyl)bisbenzene
E
isobutene
Conditions | Yield |
---|---|
In toluene at 65 - 85℃; for 7h; Rate constant; Kinetics; Thermodynamic data; ΔH(act.), ΔS(act.), various temperature; |
methanol
1,2-propanediene
A
2-Methoxypropene
B
2,2-dimethoxy-propane
C
acetone
Conditions | Yield |
---|---|
sodium hydroxide at 190℃; Rate constant; other temperatures; |
2-acyl-2,3-dimethyl-3-methoxyoxetane
A
2-Methoxypropene
B
dimethylglyoxal
Conditions | Yield |
---|---|
In various solvent(s) Product distribution; Irradiation; infrared multiphoton induced photolysis; the luminescence of the reaction mixture was also investigated; |
t-butyl heptafluoroperoxybutyrate
A
heptafluorobutyric Acid
B
2-Methoxypropene
C
acetic acid methyl ester
Conditions | Yield |
---|---|
In pyridine at 50℃; for 12h; Product distribution; | A 0.91 % Turnov. B 0.46 % Turnov. C 0.03 % Turnov. D 0.21 % Turnov. |
t-butyl heptafluoroperoxybutyrate
A
heptafluorobutyric Acid
B
2-Methoxypropene
C
tert-butyl heptafluorobutyrate
D
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
In nitrobenzene at 70℃; for 7h; Product distribution; | A 0.90 % Turnov. B 0.19 % Turnov. C 0.02 % Turnov. D 0.06 % Turnov. E 0.05 % Turnov. |
t-butyl heptafluoroperoxybutyrate
A
heptafluorobutyric Acid
B
Di-t-butyl ketone
C
2-Methoxypropene
D
tert-butyl heptafluorobutyrate
E
acetone
Conditions | Yield |
---|---|
With pyridine In benzene at 80℃; for 11h; Thermodynamic data; Rate constant; Product distribution; ΔH(excit.); ΔS(excit.); further solvents (octane, nitrobenzene, pyridine, methoxybenzene); other temperature; | A 0.63 % Turnov. B 0.04 % Turnov. C 0.15 % Turnov. D 0.02 % Turnov. E 0.02 % Turnov. |
methanol
1,2-propanediene
prop-1-yne
A
2-Methoxypropene
B
acetone
Conditions | Yield |
---|---|
sodium hydroxide; pyrographite at 150℃; Rate constant; Thermodynamic data; other temperatures; various molar ratios; other catalyst composition; |
methanol
prop-1-yne
A
2-Methoxypropene
B
2,2-dimethoxy-propane
C
acetone
Conditions | Yield |
---|---|
sodium hydroxide at 190℃; Rate constant; other temperatures; |
1-Butoxy radical
A
2,3-dihydro-2H-furan
B
4-butanolide
C
n-propyl hydroperoxide
D
2-Methoxypropene
E
butyraldehyde
F
butan-1-ol
Conditions | Yield |
---|---|
With oxygen at 69.9 - 229.9℃; Product distribution; Rate constant; Thermodynamic data; flow and static experiments; isomerization reactions in oxygen; oxidation, isomerization and decomposition; effect of reaction vessel wall conditions; reaction mechanism; |
methyl bromide
acetone enolate ion
A
2-Methoxypropene
B
butanone
Conditions | Yield |
---|---|
In gas at 39.9℃; Rate constant; |
t-butyl heptafluoroperoxybutyrate
A
heptafluorobutyric Acid
B
2-Methoxypropene
C
tert-butyl heptafluorobutyrate
D
acetone
Conditions | Yield |
---|---|
With methoxybenzene at 70℃; for 7h; Product distribution; | A 0.59 % Turnov. B 0.14 % Turnov. C 0.28 % Turnov. D 0.07 % Turnov. E n/a |
methanol
1,2-propanediene
2,2-dimethoxy-propane
prop-1-yne
2-Methoxypropene
Conditions | Yield |
---|---|
at 170℃; under 5250.53 Torr; |
Conditions | Yield |
---|---|
ZnO/SiO2 catalyst at 180 - 200℃; under 2625.26 Torr; Product distribution / selectivity; Gas phase; |
acetone
carbonic acid dimethyl ester
A
3,5,5-Trimethylcyclohex-2-en-1-one
B
4-methyl-pent-3-en-2-one
C
2-Methoxypropene
D
4-Hydroxy-4-methyl-2-pentanone
E
acetoacetic acid methyl ester
Conditions | Yield |
---|---|
With CO2 adsorbed on sodium doped MgO at 240℃; for 5h; |
2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride
A
2-Methoxypropene
Conditions | Yield |
---|---|
In dichloromethane-d2 at -78 - -65℃; for 0.175h; Equilibrium constant; Glovebox; Cooling with acetone-dry ice; |
acetic acid methyl ester
Methyltriphenylphosphonium bromide
2-Methoxypropene
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: acetic acid methyl ester In tetrahydrofuran at 20℃; Inert atmosphere; |
methanol
2,2-dimethoxy-propane
A
tetramethylorthosilicate
B
2-Methoxypropene
C
acetone
Conditions | Yield |
---|---|
With carbon dioxide; silica gel; potassium hydroxide at 240℃; under 15001.5 Torr; for 24h; Autoclave; | A 83 %Chromat. B 7 %Chromat. C 27 %Chromat. |
Conditions | Yield |
---|---|
With silica gel; potassium hydroxide In methanol at 240℃; under 15001.5 Torr; for 24h; Autoclave; | A 7 %Chromat. B 10 %Chromat. |
(E)-3-phenylpropenal
2-Methoxypropene
[(E)-5-Methoxy-3-(1-methoxy-1-methyl-ethoxy)-hexa-1,5-dienyl]-benzene
Conditions | Yield |
---|---|
With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; acetic acid In dichloromethane for 18h; Ambient temperature; | 100% |
With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; silica gel; acetic acid at 25℃; | 83% |
With silica gel; acetic acid; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium In dichloromethane at 25℃; Addition; | 83% |
2-Methoxypropene
ethyl 3-bromo-2-(hydroxyimino)propanoate
ethyl 3-bromo-2-<(1-methoxy-1-methylethoxy)imino>propanoate
Conditions | Yield |
---|---|
In dichloromethane for 6h; Ambient temperature; | 100% |
2-Methoxypropene
(1S,2R)-1-((4R,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-phenylsulfanyl-propane-1,2-diol
(4S,5S,4'R,5'R)-5-Benzhydryloxymethyl-2,2,2',2'-tetramethyl-5'-phenylsulfanylmethyl-[4,4']bi[[1,3]dioxolanyl]
Conditions | Yield |
---|---|
With (+)-10-camphorsulfonic acid In dichloromethane for 0.5h; Ambient temperature; | 100% |
2-Methoxypropene
(3RS,4S)-4-<(tert-butyloxy)carbonyl>-5-(cyclohexylmethyl)-3-hydroxy-1-pentene
3-<(tert-butyloxy)carbonyl>-4-(cyclohexylmethyl)-2,2-dimethyl-5-vinyloxazolidine
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 1h; Ambient temperature; | 100% |
2-Methoxypropene
(3R,4S)-(t-butyloxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid ethyl ester
(4S,5R)-N-Boc-5-(carbethoxymethyl)-2,2-dimethyl-4-(2-methylpropyl)-1,3-oxazolidine
Conditions | Yield |
---|---|
With trichlorophosphate for 16h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
at 0℃; for 0.333333h; | 100% |
2-Methoxypropene
3-(4-Chloro-benzylidene)-1,5-dioxa-spiro[5.5]undecane-2,4-dione
Conditions | Yield |
---|---|
at 0℃; for 0.333333h; | 100% |
2-Methoxypropene
3-(4-Nitro-benzylidene)-1,5-dioxa-spiro[5.5]undecane-2,4-dione
Conditions | Yield |
---|---|
at 0℃; for 0.333333h; | 100% |
2-Methoxypropene
3-chlorobutan-2-ol
(S)-2-Chloro-3-(1-methoxy-1-methyl-ethoxy)-butane
Conditions | Yield |
---|---|
With oxalic acid In diethyl ether for 1h; | 100% |
2-Methoxypropene
4(S)-<(tert-butyloxycarbonyl)amino>-3-hydroxy-6-methyl-1-heptene
(4S)-3-(tert-butyloxycarbonyl)-2,2-dimethyl-5-ethenyl-4-(methylpropyl)oxazolidine
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 4h; Ambient temperature; | 100% |
2-Methoxypropene
(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol
(4aR,6R,8aS)-6-Allyl-4,4a,6,8a-tetrahydro-2,2-dimethylpyrano<3,2-d>-m-dioxin
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane 1.) 0 deg C, 2 h, 2.) 3 h; | 100% |
2-Methoxypropene
1-β-D-Ribofuranosyl-3-hydroxy-4-ethoxycarbonylpyranose
1-(2,3-O-Isopropylidene-β-Dribofuranosyl)-3-hydroxy-4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; mercury dichloride In acetone at 20℃; for 3h; | 100% |
2-Methoxypropene
3β-acetoxy-17β-pivaloylandrost-5-ene-19-ol
2,2-Dimethyl-propionic acid (3S,8R,9S,10S,13S,14S,17S)-3-acetoxy-10-(1-methoxy-1-methyl-ethoxymethyl)-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,4-dioxane | 100% |
2-Methoxypropene
(4S)-(-)-4,5-dihydroxy-3-methyl-2-butenoic acid 1,4-lactone
(4S)-(-)-4-hydroxy-5-<(2-methoxypropyl)oxy>-3-methyl-2-butenoic acid lactone
Conditions | Yield |
---|---|
With trichlorophosphate for 6h; Ambient temperature; | 100% |
2-Methoxypropene
(9S)-9-dihydro-3,5-O-(p-methoxybenzylidene)erythronolide A
(9S)-9-dihydro-9,11-O-isopropylidene-3,5-O-(p-methoxybenzylidene)erythronolide
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 25℃; for 1.5h; | 100% |
With pyridinium p-toluenesulfonate In dichloromethane at 25℃; for 1.5h; |
2-Methoxypropene
(1α,2α,4β,5β)-diethyl N,N'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis
(3aα,5α,6α,7aα)-diethyl N,N'-(hexahydro-2,2-dimethyl-1,3-benzodioxole-5,6-diyl)bis
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetone for 1h; Ambient temperature; | 100% |
2-Methoxypropene
2-hydroxymethyl-4-phenylselenobutan-1-ol
2,2-dimethy-5-(2-phenylselenoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane for 1.5h; Ambient temperature; | 100% |
2-Methoxypropene
(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione
(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In acetone for 12h; Ambient temperature; | 100% |
2-Methoxypropene
(Z)-(1R,12S,13R,15S)-13,15-Bis-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-5,7,16-trioxa-tricyclo[10.3.1.04,8]hexadec-10-ene
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 0℃; for 3h; | 100% |
2-Methoxypropene
<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester
(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 2h; Ambient temperature; | 100% |
With pyridinium p-toluenesulfonate In dichloromethane at 0℃; for 2h; | 95% |
2-Methoxypropene
(1S,2S,3S)-1-(phenylthio)-1-(trimethylsilyl)-4-O-(triphenylmethyl)butane-2,3,4-triol
(1S,2S,3S)-1-(phenylthio)-2,3-O-isopropylidene-1-(trimethylsilyl)-4-O-(triphenylmethyl)butane-2,3,4-triol
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 3.5h; | 100% |
2-Methoxypropene
(1R,2R,3R)-1-(phenylthio)-1-(trimethylsilyl)-4-O-(triphenylmethyl)butane-2,3,4-triol
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 3.5h; | 100% |
2-Methoxypropene
(2S,3S)-3-benzenethio-3-(trimethylosilyl)propane-1,2-diol
(2S,3S)-3-benzenethio-1,2-O-isopropylidene-3-(trimethylsilyl)propane-1,2-diol
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 1.5h; Ambient temperature; | 100% |
2-Methoxypropene
(1R,2S,1'S,2'S)-2-(2'-tert-butoxycarbonylamino-1'-hydroxy-3'-phenylpropyl)cyclopentane-1-carboxylic acid n-butylamide
(4S,5S,1'S,2'R)-4-benzyl-3-N-tert-butoxycarbonyl-5-(2'-n-butylaminocarbonyl)cyclopentyl-2,2-dimethyloxazolidine
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 1.5h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid | 100% |
2-Methoxypropene
benzaldehyde
[3-Methoxy-1-(1-methoxy-1-methyl-ethoxy)-but-3-enyl]-benzene
Conditions | Yield |
---|---|
With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; silica gel; acetic acid at 25℃; | 100% |
With silica gel; acetic acid; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium In dichloromethane at 25℃; Addition; | 100% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid | 100% |
Conditions | Yield |
---|---|
With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; silica gel; acetic acid at 25℃; | 100% |
With silica gel; acetic acid; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium In dichloromethane at 25℃; Addition; | 99% |
2-Methoxypropene
5,6-anhydro-1,2-O-isopropylidene-α-D-glucofuranose
5,6-anhydro-1,2-O-isopropylidene-3-O-(1-methoxy-1-methyl ethyl)-α-D-glucofuranose
Conditions | Yield |
---|---|
With trifluoroacetic acid In chloroform | 100% |
With trifluoroacetic acid In dichloromethane for 4h; Ambient temperature; | 673 mg |
2-Methoxypropene
(S)-Methyl mandelate
(S)-(1-Methoxy-1-methyl-ethoxy)-phenyl-acetic acid methyl ester
Conditions | Yield |
---|---|
With dichloro-acetic acid at 20℃; for 60h; | 100% |
Molecular Structure of 2-Methoxypropene (CAS NO.116-11-0):
IUPAC Name: 2-Methoxyprop-1-ene
Molecular Formula: C4H8O
Molecular Weight: 72.11
EINECS: 204-125-3
XLogP3-AA: 1.2
H-Bond Donor: 0
H-Bond Acceptor: 1
Melting Point: < 25 °C
Index of Refraction: 1.374
Molar Refractivity: 21.89 cm3
Molar Volume: 95.8 cm3
Surface Tension: 17.5 dyne/cm
Density: 0.752 g/cm3
Flash Point: -29 °C
Enthalpy of Vaporization: 26.59 kJ/mol
Boiling Point: 32 °C at 760 mmHg
Vapour Pressure: 591 mmHg at 25 °C
Storage temp.: 2-8 °C
Water Solubility: negligible
Sensitive Light :Sensitive
Appearance: clear colorless liquid
Canonical SMILES: CC(=C)OC
InChI: InChI=1S/C4H8O/c1-4(2)5-3/h1H2,2-3H3
InChIKey: YOWQWFMSQCOSBA-UHFFFAOYSA-N
Product Categories: Propanes/propenes; Protection & Derivatization Reagents (for Synthesis); Synthetic Organic Chemistry
2-Methoxypropene (CAS NO.116-11-0) can be used for pharmaceutical intermediates.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | > 20mL/kg (20mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. | |
rat | LCLo | inhalation | 64000ppm/4H (64000ppm) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. | |
rat | LD50 | oral | 1870uL/kg (1.87mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. |
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion. Slightly toxic by inhalation.
Safety Information of 2-Methoxypropene (CAS NO.116-11-0):
Hazard Codes: F+ Xn
Risk Statements: 12-19-22
R12:Extremely flammable.
R19:May form explosive peroxides.
R22:Harmful if swallowed.
Safety Statements: 3-16-29-33-7/9-9-18
S3:Keep in a cool place.
S16:Keep away from sources of ignition.
S29:Do not empty into drains.
S33:Take precautionary measures against static discharges.
S7:Keep container tightly closed.
S9:Keep container in a well-ventilated place.
S18:Handle and open container with care.
RIDADR: UN 1993 3/PG 1
WGK Germany: 1
RTECS: UD0800000
F: 8-10
HazardClass: 3
PackingGroup: I
2-Methoxypropene (CAS NO.116-11-0), its Synonyms are 1-Propene, 2-methoxy- ; 2-Methoxy-1-propene ; Ether, isopropenyl methyl ; Isopropenyl methyl ether ; Methyl isopropenyl ether ; Propene, 2-methoxy- ; 2-Methoxyprop-1-ene .
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