Conditions | Yield |
---|---|
With chloro-trimethyl-silane at 20℃; for 0.416667h; | 97% |
With toluene-4-sulfonic acid 1.)cooling, 1 h 2.)20 deg C, 20 h; | 57% |
With C6H12Bi6O28S6 for 4h; Reflux; | 10% |
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate; sodium nitrite at 50℃; for 24h; Temperature; Time; UV-irradiation; | 67% |
2-bromomethyl-1,3-dioxolane
ethyl 3-bromobenzoate
A
2-methyl-1,3-dioxolane
B
di(1,3-dioxolan-2-yl)methane
C
benzoic acid ethyl ester
D
ethyl 3-((1,3-dioxolan-2-yl)methyl)benzoate
Conditions | Yield |
---|---|
With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 1,10-Phenanthroline; NiI2*3.5H2O; sodium iodide; zinc at 20 - 60℃; for 19h; chemoselective reaction; | A n/a B n/a C n/a D 66% E n/a |
2-ethoxy-ethanol
lead(IV) tetraacetate
A
2-methyl-1,3-dioxolane
B
2-ethoxyethyl acetate
C
ethyl acetate
Conditions | Yield |
---|---|
In chlorobenzene at 140℃; for 0.5h; | A 27% B 63% C 10% |
2-ethoxy-ethanol
A
2-methyl-1,3-dioxolane
B
2-ethoxyethyl acetate
C
ethyl acetate
Conditions | Yield |
---|---|
With lead(IV) acetate In chlorobenzene at 140℃; for 0.5h; glass tube; | A 27% B 63% C 10% |
Conditions | Yield |
---|---|
With potassium hydroxide at 120℃; Product distribution; cyclization, various alkalis; | 51% |
With sulfuric acid |
ethylene glycol
A
2-methyl-1,3-dioxolane
B
1,4-dioxane
C
acetaldehyde
D
diethylene glycol
Conditions | Yield |
---|---|
With tungsten trioxide on silica; hydrogen In water at 340℃; Temperature; Inert atmosphere; | A 38.8% B 28.7% C 44.9% D n/a |
2-ethoxy-ethanol
A
2-methyl-1,3-dioxolane
B
ethylene glycol monoformate
C
ethoxyacetaldehyde
D
formic acid ethyl ester
Conditions | Yield |
---|---|
With air; methyl nitrite; nitrogen(II) oxide at 23.85℃; under 750 Torr; for 2h; Oxidation; UV-irradiation; Further byproducts given; | A 3.4% B 36% C 24% D 43% |
Conditions | Yield |
---|---|
With synthetic silica ge at 150℃; for 24h; Kinetics; Autoclave; Green chemistry; | A 40% B 9% |
ethylene glycol
acetylene
A
2-methyl-1,3-dioxolane
B
ethylene glycol divinyl ether
C
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
With sodium hydroxide; cesium fluoride at 138 - 142℃; under 10297.1 Torr; for 3.5h; | A 4% B 11% C 26% |
Conditions | Yield |
---|---|
With silica gel In neat (no solvent) at 150℃; under 1147.61 Torr; for 7h; Autoclave; | 19% |
With silica gel at 150℃; for 7h; Kinetics; Reagent/catalyst; Autoclave; Green chemistry; | 19% |
2-(ethoxyethoxy)-ethanol
2-methyl-1,3-dioxolane
Conditions | Yield |
---|---|
at 210℃; |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; mercury(II) oxide |
Conditions | Yield |
---|---|
With hydrogenchloride |
ethylene glycol
(E)-3-Ureido-but-2-enoic acid ethyl ester
A
2-methyl-1,3-dioxolane
B
1,4-dioxane
C
acetaldehyde
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; | |
With cation exchanger Unter Entfernen des entstehenden Wassers; |
1,2-bis-(1-chloro-ethoxy)-ethane
A
2-methyl-1,3-dioxolane
B
ethylene glycol divinyl ether
Conditions | Yield |
---|---|
With N,N-diethylaniline |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid 1.) ethylene glycol, 100 deg C, 15 min; 2.) ethylene glycol; Multistep reaction; |
2-hydroxyethyl vinyl ether
A
2-methyl-1,3-dioxolane
B
methane
C
ethane
D
propane
E
potassium acetate
F
acetylene
Conditions | Yield |
---|---|
With potassium hydroxide at 170℃; Product distribution; other hydroxides (Na, Li); |
2-[2-(ethenyloxy)ethoxy]ethan-1-ol
A
2-methyl-1,3-dioxolane
B
ethanol
C
2-hydroxyethyl vinyl ether
Conditions | Yield |
---|---|
With potassium hydroxide at 170 - 250℃; Product distribution; |
carbon monoxide
A
2-methyl-1,3-dioxolane
B
ethanol
C
acetaldehyde
D
formic acid ethyl ester
Conditions | Yield |
---|---|
With hydrogen; Co(CO)8 In various solvent(s) at 200℃; under 237880 Torr; for 6h; Further byproducts given. Title compound not separated from byproducts; | A 7 mmol B 45 mmol C 3 mmol D 20 mmol |
ethylene glycol
acetone
A
2-methyl-1,3-dioxolane
B
2,2-dimethyl-1,3-dioxolane
C
diethyl acetal
D
ethanol
E
acetaldehyde
F
isopropyl alcohol
Conditions | Yield |
---|---|
With hydrogenchloride for 30h; Product distribution; Irradiation; reaction without aq. HCl; |
ethylene glycol
A
1,3-DIOXOLANE
B
2-methyl-1,3-dioxolane
C
2-hydroxymethyl-1,3-dioxolane
D
formic acid
E
acetic acid
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; oxygen In water at 150℃; for 100h; Product distribution; other acetloacetonates, also in basic solution; |
ethylene glycol
A
2-methyl-1,3-dioxolane
B
1,4-dioxane
C
acetaldehyde
Conditions | Yield |
---|---|
With Nafion-H at 175℃; for 19h; Product distribution; also in continuous flow reactor charged with Nafion-H or NaHX zeolites, at 175 deg C or 250 deg C, respectively; | A 20 % Chromat. B 71 % Chromat. C 6 % Chromat. |
With sulfuric acid In water at 110 - 140℃; Product distribution; Dehydration; cyclization; |
diethylene glycol
A
2-methyl-1,3-dioxolane
B
1,4-dioxane
C
1,4-dioxene
D
p-dioxanone
Conditions | Yield |
---|---|
With zeolite NaY; copper at 280℃; further catalysts and conditions; Yield given; | |
With zeolite NaY; copper at 280℃; Product distribution; effect of support on selectivity of dioxene formation; further catalysts and conditions; |
1,1-dimethoxyethane
ethylene glycol
A
2-methyl-1,3-dioxolane
B
methanol
C
acetaldehyde-[bis-(2-hydroxy-ethyl)-acetal]
Conditions | Yield |
---|---|
In dimethylsulfoxide-d6 at 25℃; for 24h; Product distribution; Further Variations:; reagent ratios; transacetalization; |
2-methyl-1,3-dioxolane
methyl crotonate
methyl 3-(2-methyl-1,3-dioxolan-2-yl)butanoate
Conditions | Yield |
---|---|
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 70℃; for 2.5h; Inert atmosphere; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With water under 76.0051 - 760.051 Torr; Reflux; | 99% |
With water; silica gel In neat (no solvent) at 150℃; under 1147.61 Torr; for 24h; Autoclave; | 10% |
Conditions | Yield |
---|---|
With bromine; di-tert-butyldicyclohexano-18-crown-18 In benzene at 20℃; for 0.166667h; Bromination; | 96% |
With 1,4-Dioxane Dibromide In tetrachloromethane at 29.9℃; Rate constant; Thermodynamic data; Mechanism; ΔH(excit.), ΔS(excit.), ΔG(excit.), lg A; further temp., kinetics; |
2-methyl-1,3-dioxolane
dimethyl cis-but-2-ene-1,4-dioate
2-(2-methyl-1,3-dioxolan-2-yl)butanedioic acid 1,4-dimethyl ester
Conditions | Yield |
---|---|
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 70℃; for 0.333333h; Inert atmosphere; regioselective reaction; | 96% |
With di-tert-butyl peroxide at 20℃; for 0.5h; Inert atmosphere; UV-irradiation; | 95% |
With di-tert-butyl peroxide at 20℃; under 50 Torr; for 3h; Sonication; Inert atmosphere; Photolysis; |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper (I) acetate In water; 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In acetone at 25℃; Kinetics; | 91% |
With 3,3-dimethyldioxirane In acetone at 25℃; | 91% |
With dinitrogen tetraoxide at 0℃; for 2h; var. reag.: O2 with Co(II)salt and 18-crown-6; O3 or hydroperoxides; | 84% |
2-methyl-1,3-dioxolane
(5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one
5-O-(tert-butyldimethylsilyloxymethyl)-4-C-(2-methyl-1,3-dioxolane)-tetrahydrofuran-2-one
Conditions | Yield |
---|---|
With benzophenone for 2h; Inert atmosphere; | 87% |
2-methyl-1,3-dioxolane
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper (I) acetate In water; 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper (I) acetate In water; 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper (I) acetate In water; 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper (I) acetate In water; 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; | 84% |
2-methyl-1,3-dioxolane
ethyl 2,3-dideoxy-6-O-trityl-α-D-glycero-hex-2-enopyranosid-4-ulose
Conditions | Yield |
---|---|
With trans-di-O-tert-butyl hyponitrite In acetonitrile for 1h; Heating; other substrates, other reactants; | 83% |
With trans-di-O-tert-butyl hyponitrite In acetonitrile for 1h; Heating; | 83% |
2-methyl-1,3-dioxolane
methyl vinyl ketone
A
(2-methyl-[1,3]dioxolan-2-yl)-acetic acid
B
3,3-ethylenedioxybutanal
Conditions | Yield |
---|---|
With oxygen; N-hydroxyphthalimide; cobalt(II) acetate at 25℃; | A 83% B 4% |
Conditions | Yield |
---|---|
With zinc trifluoromethanesulfonate In tetrahydrofuran at 130℃; for 24h; Microwave irradiation; Inert atmosphere; Sealed tube; | 83% |
2-methyl-1,3-dioxolane
acrylic acid methyl ester
Methyl (+/-)-2-hydroxy-3-(2-methyl-1,3-dioxolan-2-yl)propanoate
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate at 20℃; for 3h; | 81% |
With oxygen; N-hydroxyphthalimide; cobalt(II) acetate at 25℃; for 3h; | 81% |
With 4,9-(benzene-1,2-diyl)-2,4-dihydroxy-3a,4,9,9a-tetrahydro-1H-benzo[f]isoindole-1,3(2H)-dione; oxygen; cobalt(II) acetate at 20℃; under 760.051 Torr; for 5h; | 60% |
2-methyl-1,3-dioxolane
Conditions | Yield |
---|---|
With copper diacetate In 1,2-dichloro-ethane at 60℃; for 6h; Inert atmosphere; | 81% |
2-methyl-1,3-dioxolane
A
1,2-ethanediol acetate formate
B
ethylene glycol mono caprylate
Conditions | Yield |
---|---|
With oxygen; zinc(II) chloride; CoCl2 In 1,2-dimethoxyethane at 55℃; for 41h; | A 79% B 80% |
2-methyl-1,3-dioxolane
diethyl Fumarate
(2-methyl-[1,3]dioxolan-2-yl)-succinic acid diethyl ester
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; dibenzoyl peroxide In toluene at 80℃; for 1h; | 80% |
Conditions | Yield |
---|---|
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 70℃; for 1.5h; Inert atmosphere; regioselective reaction; | 80% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper (I) acetate In water; 1,2-dichloro-ethane at 60℃; for 16h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With benzophenone In acetonitrile for 2.5h; Irradiation; | 78% |
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 70℃; for 0.5h; Inert atmosphere; regioselective reaction; | 60% |
Conditions | Yield |
---|---|
With oxygen; N-hydroxyphthalimide; cobalt(II) acetate at 25℃; for 16h; | 77% |
With 4,9-(benzene-1,2-diyl)-2,4-dihydroxy-3a,4,9,9a-tetrahydro-1H-benzo[f]isoindole-1,3(2H)-dione; oxygen; cobalt(II) acetate at 20℃; under 760.051 Torr; | 58% |
2-methyl-1,3-dioxolane
norbornene
diethyl Fumarate
A
(2-methyl-[1,3]dioxolan-2-yl)-succinic acid diethyl ester
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; dibenzoyl peroxide In toluene at 80℃; for 15h; | A 12% B 77% |
2-methyl-1,3-dioxolane
benzophenone
4-Hydroxycyclopent-2-enone
Conditions | Yield |
---|---|
In acetonitrile for 2h; Irradiation; | A 75% B n/a C 7.5% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper (I) acetate In water; 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper (I) acetate In water; 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
With pyrene-1,6-dione at 50℃; for 24h; Irradiation; | 75% |
2-methyl-1,3-dioxolane
PVS
2-methyl-2-(2-(phenylsulfonyl)ethyl)-1,3-dioxolane
Conditions | Yield |
---|---|
With tetrabutylammonium decatungstate ammonium salt; sodium hydrogencarbonate In acetonitrile for 20h; Catalytic behavior; Reagent/catalyst; Solvent; UV-irradiation; Inert atmosphere; | 74% |
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 70℃; for 1.5h; Inert atmosphere; regioselective reaction; | 48% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper (I) acetate In water; 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; | 74% |
Product Name: 2-Methyl-1,3-dioxolane (CAS NO.497-26-7)
Molecular Formula: C4H8O2
Molecular Weight: 88.11g/mol
Mol File: 497-26-7.mol
Einecs: 207-841-4
Appearance: Clear colorless liquid
Boiling point: 82.4 °C at 760 mmHg
Storage Temperature: Flammables area
Flash Point: 4 °C
Density: 0.97 g/cm3
Refractive index: n20/D 1.398(lit.)
Sensitive: Moisture Sensitive
Surface Tension: 27.9 dyne/cm
Enthalpy of Vaporization: 30.96 kJ/mol
Vapour Pressure: 87.6 mmHg at 25°C
XLogP3-AA: 0.2
H-Bond Donor: 0
H-Bond Acceptor: 2
Product Categories: Dioxanes & Dioxolanes; Dioxolanes
1. | skn-rbt 500 mg/24H MLD | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,797. | ||
2. | eye-rbt 20 mg/24H MOD | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,797. | ||
3. | orl-rat LD50:2900 mg/kg | GISAAA Gigiena i Sanitariya. 47 (8)(1982),89. | ||
4. | ihl-rat LC50:80 g/m3 | GISAAA Gigiena i Sanitariya. 39 (11)(1974),94. | ||
5. | orl-mus LD50:3500 mg/kg | GISAAA Gigiena i Sanitariya. 39 (11)(1974),94. | ||
6. | ihl-mus LC50:59 g/m3 | GISAAA Gigiena i Sanitariya. 39 (11)(1974),94. |
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion. Mildly toxic by inhalation. A skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of 2-Methyl-1,3-dioxolane (CAS NO.497-26-7):
Hazard Codes: F,Xi
Risk Statements: 11-36
11: Highly Flammable
36: Irritating to the eyes
Safety Statements: 16-26
16: Keep away from sources of ignition - No smoking
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
2-Methyl-1,3-dioxolane ,its CAS NO. is 497-26-7,the synonyms is 2-Methyl-1,3-dioxacyclopentane ; 2-Methyl-3-dioxolane ; 2-Methyldioxolane ; Acetaldehyde ethylene acetal ; 2-Methyl-1,3-dioxolane ; Methyldioxolane .
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