Conditions | Yield |
---|---|
Stage #1: formaldehyd; carbon monoxide With 1,3,5-Trioxan; hydrogenchloride; oxalic acid In 1,4-dioxane; water; 1,2-dichloro-ethane; toluene at 165℃; under 45004.5 Torr; Stage #2: ethanol In 1,4-dioxane; water; 1,2-dichloro-ethane; toluene at 170℃; under 12001.2 Torr; for 36h; | 98.3% |
Conditions | Yield |
---|---|
With ethanol; C42H44ClN4P2Ru(1+)*Cl(1-); potassium tert-butylate at 80℃; for 5h; Schlenk technique; Inert atmosphere; | 94% |
With Ag/SiO2; hydrogen In ethanol at 84 - 242℃; under 22502.3 - 23402.3 Torr; Temperature; | |
With hydrogen; copper at 210 - 220℃; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 10h; Reflux; | A n/a B 82.8% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 10h; Reflux; | 81.8% |
With sulfuric acid at 60℃; for 3h; | 80% |
With ion exchanger (Dowex 50WX8) In chloroform for 72h; Heating; | 74% |
Conditions | Yield |
---|---|
With water at 25℃; for 24h; Green chemistry; | 80% |
With water; acetic acid In dichloromethane for 72h; Darkness; | 66% |
With copper(II) sulfate at 130℃; for 6h; | 20% |
With hydrogen fluoride | |
With Pt(II)halide; water |
Conditions | Yield |
---|---|
With hydrogenchloride; water at -10 - -5℃; for 4h; Reflux; | 78.85% |
Conditions | Yield |
---|---|
With zeolite MFI-ATSn for 6h; Reagent/catalyst; Time; Sealed tube; Green chemistry; | 69% |
ethanol
betaine
A
ethyl 2-hydroxyacetate
B
N-<(ethoxycarbonyl)methyl>trimethylammonium chloride
Conditions | Yield |
---|---|
With chloroacetic acid ethyl ester at 40℃; for 192h; | A 55% B 66% |
ethyl bromoacetate
A
nitroacetic acid ethyl ester
B
ethyl 2-hydroxyacetate
Conditions | Yield |
---|---|
With Amberlite IRA 900 NO2- form In acetonitrile at -15℃; | A 65% B 28% |
Conditions | Yield |
---|---|
With ethyl bromoacetate 1) 22 h, 50 deg C, 2) 90 min, reflux, 3) 50 deg C; | 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% |
diazoacetic acid ethyl ester
4-phenyl-butan-1-ol
A
ethyl 2-hydroxyacetate
Conditions | Yield |
---|---|
[Rh(OPiv)2]2 In water | A n/a B 45% |
[Rh(OPiv)2]2 In water for 2.75h; | A n/a B 45% |
ethyl 2-hydroxyacetate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water at 30℃; | 44% |
ethyl N-nitroso-N-(triphenylmethyl)glycinate
A
triphenylmethyl alcohol
B
ethyl 2-hydroxyacetate
C
triphenylmethane
Conditions | Yield |
---|---|
In neat (no solvent) at 180℃; for 4h; Product distribution; Mechanism; | A 43% B 10% C 16% |
diazoacetic acid ethyl ester
A
ethyl 2-hydroxyacetate
B
ethyl 2-nitrooxyacetate
Conditions | Yield |
---|---|
With sodium nitrate; water; nitric acid |
Conditions | Yield |
---|---|
With 1,4-dioxane; sodium hydroxide; water Behandeln des mit Aethanol versetzten Reaktionsgemisches mit Chlorwasserstoff und anschliessenden Erwaermen; |
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
at 120 - 130℃; im geschlossenen Gefaess; | |
at 120 - 130℃; im geschlossenen Gefaess; | |
at 120 - 130℃; |
Conditions | Yield |
---|---|
With sodium acetate at 150℃; |
chloroacetic acid ethyl ester
A
ethyl 2-fluoroacetate
B
ethyl 2-hydroxyacetate
Conditions | Yield |
---|---|
With potassium fluoride; ethanol |
Conditions | Yield |
---|---|
With water; formamide at 150℃; |
Conditions | Yield |
---|---|
at 120 - 130℃; Reaktion des Natriumsalzes; |
diazoacetic acid ethyl ester
dimethylacetylene
A
4,5-dimethyl-2(5H)-furanone
B
ethyl 2-hydroxyacetate
C
2,3-dimethyl-1-ethoxycarbonylcyclopropene
D
2-Ethoxy-4,5-dimethyl-furan
E
Diethyl maleate
Conditions | Yield |
---|---|
With copper(II) sulfate at 100℃; for 2h; Product distribution; influence of temperature, other catalyst; | A 4 % Chromat. B 7 % Chromat. C 2 % Chromat. D 15 % Chromat. E 9 % Chromat. |
diazoacetic acid ethyl ester
prop-1-yne
A
4-methyl-2(5H)-furanone
B
ethyl 2-hydroxyacetate
C
ethyl ester of 3-pentynoic acid
D
ethyl ester of 1-methylcyclopropene-3-carboxylic acid
Conditions | Yield |
---|---|
With copper(II) sulfate at 100℃; for 2h; Further byproducts given; | A 3 % Chromat. B 2 % Chromat. C 12 % Chromat. D 1.4 % Chromat. |
diazoacetic acid ethyl ester
prop-1-yne
A
4-methyl-2(5H)-furanone
B
ethyl 2-hydroxyacetate
C
ethyl ester of 3-pentynoic acid
D
ethyl ester of 1-methylcyclopropene-3-carboxylic acid
E
Diethyl maleate
Conditions | Yield |
---|---|
With copper(II) sulfate at 100℃; for 2h; Product distribution; influence of temperature, other catalyst; | A 3 % Chromat. B 2 % Chromat. C 12 % Chromat. D 1.4 % Chromat. E 6 % Chromat. |
diazoacetic acid ethyl ester
A
diethyl diglycolate
B
ethyl 2-hydroxyacetate
C
ethyl 2-cyclohexylacetate
D
diethyl Fumarate
E
Diethyl maleate
Conditions | Yield |
---|---|
NaCuX-79 In cyclohexane at 24.9℃; Product distribution; effect of the type of the catalyst; |
Conditions | Yield |
---|---|
for 5h; Heating; | 91 % Chromat. |
Conditions | Yield |
---|---|
beim Kochen; |
Conditions | Yield |
---|---|
With ammonia In methanol at 20℃; | 100% |
With ammonia for 24h; Ambient temperature; | 90% |
With ammonia |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 10℃; for 1h; Solvent; | 100% |
With chloroform |
ethyl 2-hydroxyacetate
tert-butyldimethylsilyl chloride
ethyl 2-(tert-butyldimethylsilyloxy)acetate
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 1h; Ambient temperature; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere; | 100% |
With 1H-imidazole In dichloromethane at 0℃; for 1h; | 100% |
ethyl 2-hydroxyacetate
2-chloro-3-methyl-1,3,2-oxazaphospholidine
2-(Ethoxycarbonyl)methoxy-3-methyl-1,3,2-oxazaphosphacyclopentane
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 1h; -60 deg C to RT; | 100% |
Conditions | Yield |
---|---|
In dichloromethane for 1h; | 100% |
4-chloro-5-fluoro-nicotinic acid ethyl ester
ethyl 2-hydroxyacetate
7-fluoro-3-hydroxy-furo[3,2-c]pyridine-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; | 100% |
ethyl 2,4-dichloropyridine-3-carboxylate
ethyl 2-hydroxyacetate
4-chloro-3-hydroxy-furo[3,2-c]pyridine-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 3h; | 100% |
triethylsilyl chloride
ethyl 2-hydroxyacetate
α-(triethylsiloxy)acetic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
With dmap In pyridine at 20℃; for 0.666667h; Inert atmosphere; | 99% |
With 1H-imidazole In dichloromethane at 20℃; for 10h; Inert atmosphere; |
ethyl 2-hydroxyacetate
tert-butylchlorodiphenylsilane
2-((tert-butyl(diphenyl)silyl)oxy)acetic acid ethyl ester
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 4.5h; | 100% |
With 1H-imidazole In dichloromethane at 20℃; for 16h; Cooling with ice; | 91% |
With 1H-imidazole In dichloromethane at 20℃; for 5.33333h; | 47.6% |
With 1H-imidazole; dmap In dichloromethane at 0 - 15℃; for 2h; | |
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 1.3h; Inert atmosphere; | 8.3 g |
ethyl 2-hydroxyacetate
(R)-1-phenyl-ethyl-amine
1,1'-carbonyldiimidazole
Conditions | Yield |
---|---|
Stage #1: ethyl 2-hydroxyacetate; (R)-1-phenyl-ethyl-amine With sodium methylate In methanol at 120℃; for 1.5h; Stage #2: 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1h; | 100% |
ethyl 2-hydroxyacetate
1,2,3-trichlorobenzene
(dichloro-2,3 phenoxy)acetate d'ethyle
Conditions | Yield |
---|---|
Stage #1: ethyl 2-hydroxyacetate With potassium methanolate at 30℃; Stage #2: 1,2,3-trichlorobenzene at 100℃; | 99.1% |
3,4-dihydro-2H-pyran
ethyl 2-hydroxyacetate
ethyl (tetrahydropyranyloxy)acetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 25℃; for 1h; | 99% |
toluene-4-sulfonic acid In toluene at 20℃; Product distribution / selectivity; Industrial scale; | 94.7% |
With toluene-4-sulfonic acid at 20℃; | 91.5% |
ethyl 2-hydroxyacetate
3-tert-2-chloro-1,3,2-oxazaphosphacyclopentane
3-tert-butyl-2-ethoxycarbonylmethoxy-1,3,2-oxazaphosphacyclopentane
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 1h; -60 deg C to rt; | 99% |
ethyl 2-hydroxyacetate
chlorodimethyl(1,1,2-trimethylpropyl)silane
[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-acetic acid ethyl ester
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 99% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 23℃; for 4h; | 99% |
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Time; |
Conditions | Yield |
---|---|
In water at 20℃; for 16h; | 98% |
In water at 20℃; for 18h; | 58% |
ethyl 2-hydroxyacetate
di-tert-butyl dicarbonate
ethyl 2-(tert-butoxycarbonyloxy)acetate
Conditions | Yield |
---|---|
With dmap In acetonitrile at 20℃; for 18h; | 98% |
ethyl 2-hydroxyacetate
(R)-1-(4-chlorophenyl)ethylamine
1,1'-carbonyldiimidazole
Conditions | Yield |
---|---|
Stage #1: ethyl 2-hydroxyacetate; (R)-1-(4-chlorophenyl)ethylamine With sodium methylate In methanol at 120℃; for 2h; Stage #2: 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 2h; | 98% |
ethyl 2-hydroxyacetate
2-bromo-5-(trifluoromethyl)-pyrazine
Conditions | Yield |
---|---|
Stage #1: ethyl 2-hydroxyacetate With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-bromo-5-(trifluoromethyl)-pyrazine In tetrahydrofuran at 20℃; | 98% |
Stage #1: ethyl 2-hydroxyacetate With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-bromo-5-(trifluoromethyl)-pyrazine In tetrahydrofuran at 20℃; |
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 15 - 20℃; for 1h; | 97% |
In ethanol |
ethyl 2-hydroxyacetate
o-phenylenediamine dihydrochloride
2-(Hydroxymethyl)benzimidazole
Conditions | Yield |
---|---|
In ethylene glycol for 0.025h; microwave irradiation; | 97% |
ethyl 2-hydroxyacetate
1,2-dichloro-4-fluoro-5-nitrobenzene
ethyl [(4,5-dichloro-2-nitrophenyl)oxy]acetate
Conditions | Yield |
---|---|
With potassium fluoride In 1,4-dioxane at 100℃; for 2h; | 96% |
With potassium fluoride In 1,4-dioxane at 100℃; | 96% |
ethyl 2-hydroxyacetate
3,7-didodecyl-2,8-dioxo-3,7-diaza-1,5,9-nonanetriol
Conditions | Yield |
---|---|
In toluene | 96% |
ethyl 2-hydroxyacetate
methanesulfonyl chloride
ethyl α-methanesulfonyloxyacetate
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 0 - 20℃; for 1h; | 95% |
With triethylamine In dichloromethane for 1h; | 68% |
4,5-dibromonicotinic acid ethyl ester
ethyl 2-hydroxyacetate
ethyl 7-bromo-3-hydroxy-furo[3,2-c]pyridine-2-carboxylate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2.25h; | 95% |
ethyl 2-hydroxyacetate
propynoic acid methyl ester
methyl (E)-3-(2-ethoxy-2-oxoethoxy)acrylate
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane | 95% |
ethyl 2-hydroxyacetate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Cooling with ice; | 95% |
ethyl 2-hydroxyacetate
hydrocinnamic acid chloride
carboethoxymethyl hydrocinnamate
Conditions | Yield |
---|---|
With pyridine In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere; | 95% |
IUPAC Name: Ethyl 2-hydroxyacetate
Following is the structure of Ethyl glycolate (CAS NO.623-50-7):
Empirical Formula: C4H8O3
Molecular Weight: 104.1045
EINECS: 210-798-4
Index of Refraction: 1.414
Molar Refractivity: 23.89 cm3
Molar Volume: 95.5 cm3
Density: 1.089 g/cm3
Flash Point: 61.7 °C
Surface Tension: 35.2 dyne/cm
Enthalpy of Vaporization: 45.82 kJ/mol
Boiling Point: 156.7 °C at 760 mmHg
Vapour Pressure: 1.03 mmHg at 25 °C
Appearance of Ethyl glycolate (CAS NO.623-50-7): clear colorless liquid
Product Categories: C2 to C5 ; Carbonyl Compounds ; Esters
Canonical SMILES: CCOC(=O)CO
InChI: InChI=1S/C4H8O3/c1-2-7-4(6)3-5/h5H,2-3H2,1H3
InChIKey: ZANNOFHADGWOLI-UHFFFAOYSA-N
Ethyl glycolate (CAS NO.623-50-7) can be used in organic synthesis . It also can be used as solvents.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LDLo | intraperitoneal | 1500mg/kg (1500mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Journal of Pharmacy and Pharmacology. Vol. 11, Pg. 150, 1959. |
Reported in EPA TSCA Inventory.
Moderately toxic by intraperitoneal route. An eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes of Ethyl glycolate (CAS NO.623-50-7): Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39: Wear suitable gloves and eye/face protection
WGK Germany: 3
RTECS: MC5410000
HazardClass: 3.2
PackingGroup: III
Ethyl glycolate , its cas register number 623-50-7. It also can be called Ethyl hydroxyacetate ; Hydroxyacetic acid ethyl ester ; and Acetic acid, 2-hydroxy-, ethyl ester . Ethyl glycolate (CAS NO.623-50-7) should avoid the condition like incompatible materials. It is not compatible with strong oxidizing agents, strong bases. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide. However, its hazardous polymerization has not been reported.
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