Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In chlorobenzene at 80℃; for 5h; | 100% |
With sodium persulfate; water at 20℃; for 12h; Reagent/catalyst; | 100% |
With tetrabutylphosphonium peroxotantalate; dihydrogen peroxide In water at 0℃; for 5.5h; Schlenk technique; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at -5 - 15℃; for 6h; Large scale; | 98.5% |
With sodium hydroxide In water at 18 - 36℃; under 18.7519 Torr; Temperature; Pressure; Concentration; Industrial scale; | 97.92% |
With sodium methylate In methanol at 0 - 15℃; under 2100.21 - 2325.23 Torr; for 0.833333h; Pressure; Temperature; | 93.76% |
Conditions | Yield |
---|---|
With zinc(II) nitrate; 1-butyl-3-methylimidazolium nitrate at 175℃; under 20.027 Torr; for 2.5h; | 98.2% |
With zinc-lanthanum mixed oxides at 180℃; under 375.038 Torr; Reagent/catalyst; | 76.22% |
With sodium sulfate at 140 - 180℃; for 3h; Green chemistry; | 33% |
methanol
A
oxiranyl-methanol
B
bis(4-methoxyphenyl)phenylmethyl methyl ether
Conditions | Yield |
---|---|
With lithium tetrafluoroborate In dichloromethane at 20℃; for 0.25h; deprotection; | A 92% B n/a |
glycerol
carbonic acid dimethyl ester
A
4-hydroxymethyl-1,3-dioxolan-2-one
B
oxiranyl-methanol
Conditions | Yield |
---|---|
With 30 wt.% KF/γ-Al2O3 at 80℃; for 1.5h; Catalytic behavior; Reagent/catalyst; | A 91.3% B n/a |
With fluorinated Mg-Al hydrotalcite derived basic catalyst at 110℃; for 3h; Reagent/catalyst; | A 80.5% B 10.8% |
With Mg/Zr/Sr mixed oxide at 90℃; for 1.5h; Catalytic behavior; Temperature; Concentration; Reagent/catalyst; | A 56% B 40% |
2-fluoroethanol
2-fluoro-2-phenylethanol
A
trans-3-chloroallyl 2,3-epoxypropyl ether
B
2-(2-Fluoro-2-phenyl-ethoxymethyl)-oxirane
C
oxiranyl-methanol
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 25℃; for 24h; Yields of byproduct given; | A n/a B 75% C n/a |
2-fluoroethanol
trans-2-fluorocyclohexanol
2-((1S,2S)-2-Fluoro-cyclohexyloxymethyl)-oxirane
B
trans-3-chloroallyl 2,3-epoxypropyl ether
C
oxiranyl-methanol
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 25℃; for 24h; Yields of byproduct given; | A 65% B n/a C n/a |
4-hydroxymethyl-1,3-dioxolan-2-one
A
2,5-Bis(hydroxymethyl)-1,4-dioxane
C
3-(oxrian-2-yloxy)propane-1,2-diol
D
oxiranyl-methanol
Conditions | Yield |
---|---|
With sodium chloride at 175℃; under 20.027 Torr; for 0.75h; | A n/a B n/a C n/a D 62% |
glycerol
A
1,3-dioxolane-4-methanol
B
glycerol formal
C
glycolic Acid
D
ethyl 2-hydroxyacetate
E
diglycerol
F
oxiranyl-methanol
G
hydroxy-2-propanone
H
acrolein
Conditions | Yield |
---|---|
With pretreated aluminium vanadium phosphate In water at 280℃; under 760.051 Torr; Catalytic behavior; Activation energy; Reagent/catalyst; Temperature; | A n/a B n/a C n/a D n/a E n/a F n/a G n/a H 62% |
glycerol
carbonic acid dimethyl ester
A
4-hydroxymethyl-1,3-dioxolan-2-one
B
methyl ((2-oxo-1,3-dioxolan-4-yl)methyl)carbonate
C
oxiranyl-methanol
Conditions | Yield |
---|---|
With potassium fluoride at 80℃; for 1.5h; Catalytic behavior; Reagent/catalyst; | A 58.4% B n/a C n/a |
With tetrabutylammomium bromide at 160℃; under 8250.83 Torr; for 0.05h; Flow reactor; |
ethanol
4-chloromethyl-1,3,2-dioxathiolane 2-oxide
phenol
A
diethyl sulphite
B
1-phenoxy-2,3-propanediol
C
oxiranyl-methanol
Conditions | Yield |
---|---|
With sodium In toluene for 1h; Heating; | A 20% B 45% C n/a |
Conditions | Yield |
---|---|
With titanium-containing zeolite In methanol at 35℃; Mechanism; Solvent; | A n/a B 29.3% |
Conditions | Yield |
---|---|
at 150℃; under 35 Torr; Erhitzen des Reaktionsprodukts unter 10-15 Torr bis auf 240grad; | |
at 240℃; under 10 - 15 Torr; |
[1,3]-dioxolan-2-one
glycerol
A
oxiranyl-methanol
B
ethylene glycol
Conditions | Yield |
---|---|
at 240℃; unter vermindertem Druck; |
3-iodo-propane-1,2-diol
silver(1+) stearate
A
oxiranyl-methanol
B
stearic acid
Conditions | Yield |
---|---|
verreibt man geschmolzenes Glycerin-α-jodhydrin; | |
at 100℃; under 5 Torr; 3/4 Stdn. Erhitzen; | |
at 100℃; under 5 Torr; beim Verreiben oder 3/4 stdg.Erhitzen; |
Conditions | Yield |
---|---|
With silver(1+) stearate at 100℃; under 5 Torr; |
3-monochloro-1,2-propanediol
glycerol
A
diglycerol
B
oxiranyl-methanol
Conditions | Yield |
---|---|
die Mononatriumverbindung reagiert; |
glycerol
A
3-Hydroxypropanal
B
diglycerol
C
oxiranyl-methanol
D
hydroxy-2-propanone
Conditions | Yield |
---|---|
at 170 - 250℃; Produkt 5: Acrylaldehyd; |
Conditions | Yield |
---|---|
With potassium acetate Behandeln des entstandenen Glycidacetats in aether. Loesung mit gepulvertem Aetznatron; | |
With potassium acetate at 150℃; Behandeln des entstandenen Glycidacetats in aether. Loesung mit gepulvertem Aetznatron; |
Conditions | Yield |
---|---|
With water; aluminum tri-tert-butoxide 1.) benzene, 20 deg C, 8 h, 2.) benzene; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With 1-propenylbenzene; dihydrogen peroxide In tetrahydrofuran Product distribution; Ambient temperature; competition experiments for intra- vs. intermolecular epoxidation; |
(+/-)-2,3-dihydroxypropyl tosylate
oxiranyl-methanol
Conditions | Yield |
---|---|
Mechanism; |
ethanol
allyl alcohol
A
3-ethoxy-1,2-propanediol
B
2-ethoxy-propane-1,3-diol
C
oxiranyl-methanol
D
glycerol
Conditions | Yield |
---|---|
With titanium silicate; dihydrogen peroxide In ethanol at 65℃; for 24h; Product distribution; var. temp., var. time, var. solvent, var. acidity of TS-1; |
butanoic acid ethyl ester
allyl alcohol
A
(+/-)-glycidyl butyrate
B
allyl butyrate
C
oxiranyl-methanol
Conditions | Yield |
---|---|
With Novozym 435; dihydrogen peroxide 1.) 15 min, 2.) 40 deg C, 16 h; Yield given. Multistep reaction. Yields of byproduct given; |
oxiranyl-methanol
benzoyl chloride
oxiran-2-ylmethyl benzoate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0℃; for 1h; | 100% |
With pyridine; dmap In dichloromethane | 94% |
With dmap In dichloromethane at 20℃; for 24h; | 90% |
oxiranyl-methanol
N-methylaniline
3-(methyl(phenyl)amino)propane-1,2-diol
Conditions | Yield |
---|---|
In methanol for 48h; Reflux; | 100% |
In ethanol at 120℃; for 0.333333h; Microwave irradiation; | 81% |
triethylsilyl chloride
oxiranyl-methanol
triethyl(oxiran-2-ylmethoxy)silane
Conditions | Yield |
---|---|
With 1H-imidazole; triethylamine In N,N-dimethyl-formamide silylation; | 100% |
With 1H-imidazole; dmap In dichloromethane at 20℃; for 1h; Inert atmosphere; | 100% |
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; for 3h; | 95% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 84% |
With pyridine In diethyl ether for 0.75h; |
Conditions | Yield |
---|---|
With C25H13O12Si(5-)*3Ni(2+)*HO(1-); tetrabutylammomium bromide In neat (no solvent) at 99.84℃; under 7500.75 Torr; for 3h; Catalytic behavior; Autoclave; | 100% |
With tetrabutylammomium bromide In neat (no solvent) at 60℃; under 7500.75 Torr; for 3h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave; Green chemistry; | 99% |
With Cu7(H1L)2(TPT)3(H2O)6; tetrabutylammomium bromide at 100℃; under 760.051 Torr; for 3h; Catalytic behavior; Kinetics; Autoclave; | 99% |
Conditions | Yield |
---|---|
Stage #1: oxiranyl-methanol With sodium hydride In tetrahydrofuran at 0℃; Stage #2: benzyl bromide In tetrahydrofuran for 7h; | 100% |
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; | 98% |
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; | 98% |
oxiranyl-methanol
3-(2,3-dihydroxypropyl)-5,5-dimethylhydantoin
Conditions | Yield |
---|---|
With lithium chloride In isopropyl alcohol at 80℃; for 3h; | 100% |
oxiranyl-methanol
3-(2-hydroxypropyl)-5,5-dimethylhydantoin
Conditions | Yield |
---|---|
With lithium chloride In isopropyl alcohol at 80℃; for 3h; | 100% |
oxiranyl-methanol
tert-butylchlorodiphenylsilane
tert-butyl(oxiran-2-ylmethoxy)diphenylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 0 - 21℃; for 17h; Schlenk technique; | 100% |
With 1H-imidazole In chloroform for 1h; Ambient temperature; | 97% |
With 1H-imidazole In dichloromethane at 20℃; | 90% |
N-(2-iodophenyl)benzenesulfonamide
oxiranyl-methanol
N-(2-Iodo-phenyl)-N-oxiranylmethyl-benzenesulfonamide
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; Inert atmosphere; | 100% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 1h; Ambient temperature; | 80% |
Conditions | Yield |
---|---|
With triethylamine In toluene at -20 - -10℃; for 20h; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at 4℃; for 5.5h; | 51% |
With triethylamine In dichloromethane at 0℃; for 1.25h; | 5 g |
Stage #1: oxiranyl-methanol With triethylamine In dichloromethane at 0℃; for 0.25h; Stage #2: 3-nitrobenzenesulphonyl chloride In dichloromethane at 0℃; for 1h; | 5 g |
Conditions | Yield |
---|---|
at 0 - 50℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In water for 72h; | 100% |
1,1,1-tri(hydroxymethyl)propane
2-oxiranylmethylisoindole-1,3-dione
oxiranyl-methanol
Conditions | Yield |
---|---|
Stage #1: 1,1,1-tri(hydroxymethyl)propane With potassium tert-butylate In tetrahydrofuran at 120℃; for 18h; Inert atmosphere; Stage #2: oxiranyl-methanol In tetrahydrofuran at 120℃; for 0.5h; Inert atmosphere; Stage #3: 2-oxiranylmethylisoindole-1,3-dione In tetrahydrofuran at 120℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
erbium(III) triflate at 20℃; for 48h; | 99% |
ruthenium trichloride for 2h; Cycloaddition; Heating; | 89% |
iron(III) trifluoroacetate for 4h; acetonide formation; Heating; | 89% |
With boron fluoride ether |
(Z)-9-octadecenoyl chloride
oxiranyl-methanol
(Z)-(oxiran-2-yl)methyl octadec-9-enoate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 99% |
With triethylamine In acetonitrile at 0 - 20℃; for 12.5h; Inert atmosphere; | 91% |
With dmap In dichloromethane at 20℃; for 4h; | 86% |
With triethylamine In diethyl ether for 12h; Ambient temperature; | 1.00 g |
4-(2-hydroxyethylamino)-2-methyl-6,7-dihydropyrimido<5,4-b><1,4>oxazin-7(8H)-one
oxiranyl-methanol
8-(2,3-Dihydroxy-propyl)-4-(2-hydroxy-ethylamino)-2-methyl-8H-pyrimido[5,4-b][1,4]oxazin-7-one
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In benzene | 99% |
Conditions | Yield |
---|---|
In ethanol at 140℃; under 2585.81 Torr; for 0.0666667h; microwave irradiation; | 99% |
1,2,3,4-tetrahydroisoquinoline
oxiranyl-methanol
3-(3,4-dihydroisoquinolin-2(1H)-yl)propane-1,2-diol
Conditions | Yield |
---|---|
In ethanol at 140℃; under 2585.81 Torr; for 0.0666667h; microwave irradiation; | 99% |
1-(2-Methoxyphenyl)piperazine
oxiranyl-methanol
3-<4-(2-Methoxyphenyl)piperazinyl>-1,2-propandiol
Conditions | Yield |
---|---|
In ethanol at 140℃; under 2585.81 Torr; for 0.0666667h; microwave irradiation; | 99% |
Conditions | Yield |
---|---|
In dichloromethane react. GaMe3 with 1 equiv. rac-2,3-epoxy-1-propanol (CH2Cl2, -78°C); | 99% |
oxiranyl-methanol
(2R,2‘R)-di-tert-butyl 3,3‘-disulfanediylbis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate)
Conditions | Yield |
---|---|
Stage #1: (2R,2‘R)-di-tert-butyl 3,3‘-disulfanediylbis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate) With hydrogenchloride; sulfuric acid; zinc In methanol; dichloromethane; water at 20℃; for 0.25h; Inert atmosphere; Stage #2: oxiranyl-methanol In methanol; dichloromethane; water at 40℃; for 5h; Inert atmosphere; | 99% |
Stage #1: (2R,2‘R)-di-tert-butyl 3,3‘-disulfanediylbis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate) With hydrogenchloride; sulfuric acid; zinc In methanol; dichloromethane at 0℃; for 0.5h; Stage #2: oxiranyl-methanol In methanol; dichloromethane at 40℃; for 3h; | 84% |
Conditions | Yield |
---|---|
In acetone at 50℃; for 6.5h; | 99% |
Conditions | Yield |
---|---|
With 2-methylimidazole at 25 - 40℃; for 168h; Sealed tube; | 99% |
Conditions | Yield |
---|---|
at 55℃; under 225.023 - 31503.2 Torr; for 0.666667h; Pressure; Autoclave; Green chemistry; | 98.99% |
In water at 30℃; for 4 - 5h; | 92.7% |
unter Kuehlung; |
Conditions | Yield |
---|---|
With water at 60℃; for 4h; | 98% |
With water at 70℃; Rate constant; variation of pH; | |
With sulfuric acid; water |
oxiranyl-methanol
benzyl isothiocyanate
benzylcarbamic acid oxiranylmethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 24h; | 98% |
With sodium carbonate In toluene for 2h; Heating; | 76% |
With 1,3-dichlorotetrabutyldistannoxane In dichloromethane | 62% |
With 1,3-dichlorotetrabutyldistannoxane In dichloromethane at 20℃; for 48h; | 62% |
1.Glycidol is used as a stabilizer for natural oils and vinyl polymers and as a demulsifier.
2.Used in surface coatings, pharmaceuticals, chemical synthesis, and as a gelation agent in solid propellants etc.
3.As a chemical intermediate in the synthesis of glycerol, esters,amines and glycidyl ethers,.
1. | skn-rbt 558 mg/3D MOD | AMIHAB AMA Archives of Industrial Health. 14 (1956),250. | ||
2. | mmo-klp 200 µmol/L | MUREAV Mutation Research. 89 (1981),269. | ||
3. | cyt-hmn:lym 400 µmol/L | MUREAV Mutation Research. 91 (1981),243. | ||
4. | orl-rat LD50:420 mg/kg | FCTXAV Food and Cosmetics Toxicology. 19 (1981),347. | ||
5. | ihl-rat LC50:580 ppm/8H | AMIHAB AMA Archives of Industrial Health. 14 (1956),250. | ||
6. | ipr-rat LD50:200 mg/kg | FCTXAV Food and Cosmetics Toxicology. 19 (1981),347. | ||
7. | orl-mus LD50:431 mg/kg | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 24 (3)(1980),42. | ||
8. | ihl-mus LC50:450 ppm/4H | AMIHAB AMA Archives of Industrial Health. 14 (1956),250. | ||
9. | ipr-mus LDLo:500 mg/kg | PSEBAA Proceedings of the Society for Experimental Biology and Medicine. 35 (1936),98. | ||
10. | skn-rbt LD50:1980 mg/kg | AMIHAB AMA Archives of Industrial Health. 14 (1956),250. |
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