Conditions | Yield |
---|---|
With Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 3h; Catalytic behavior; Irradiation; | 94% |
Conditions | Yield |
---|---|
at 149.84℃; under 22502.3 Torr; for 3h; Inert atmosphere; | A 79.3% B 21.4% |
oxirane
ethanol
carbon dioxide
A
[1,3]-dioxolan-2-one
B
2-ethoxy-ethanol
C
ethylene glycol
Conditions | Yield |
---|---|
With lanthanum(III) oxide; potassium iodide at 149.84℃; under 22502.3 Torr; for 3h; | A 77.3% B 14.1% C 6.8% |
Conditions | Yield |
---|---|
With carbon dioxide at 149.84℃; under 22502.3 Torr; for 3h; | 47.2% |
in Gegenwart aktivierten Hydrosilicaten; | |
With hydrogen fluoride at 81℃; |
oxirane
ethanol
carbon dioxide
A
[1,3]-dioxolan-2-one
B
2-ethoxy-ethanol
C
ethylene glycol
D
Diethyl carbonate
Conditions | Yield |
---|---|
With sodium ethanolate; potassium bromide at 423℃; under 22502.3 Torr; for 3h; | A 44.4% B 6.5% C 39.2% D 29.6% |
With sodium ethanolate at 149.84℃; under 22502.3 Torr; for 3h; | A 19.1% B 42.6% C 16.8% D 11.6% |
With potassium ethoxide at 149.84℃; under 22502.3 Torr; for 3h; | A 33.1% B 28.3% C 21.6% D 12.8% |
Conditions | Yield |
---|---|
With sulfuric acid at 100 - 130℃; im Autoklaven; | |
With toluene-4-sulfonic acid at 100 - 130℃; | |
With 2,3-Dimethylaniline at 100 - 130℃; | |
With sulfuric acid at 80 - 100℃; | |
With metal oxide at 100 - 130℃; |
Conditions | Yield |
---|---|
With nickel; barium(II) oxide at 130 - 150℃; Hydrogenation.unter Druck; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether |
1-ethoxy-2-trityloxy-ethane
A
2-ethoxy-ethanol
B
monoethylene glycol diethyl ether
C
triphenylmethane
D
acetaldehyde
Conditions | Yield |
---|---|
at 325 - 330℃; |
sodium 2-hydroxyethoxide
ethyl iodide
2-ethoxy-ethanol
Conditions | Yield |
---|---|
With sodium |
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With sodium hydroxide |
2-methyl-1,3-dioxolane
triethylaluminum
A
2-ethoxy-ethanol
B
2-(1-Methylpropoxy)ethanol
Conditions | Yield |
---|---|
With diethylaluminium hydride In hexane; kerosene for 50h; Heating; | A 0.01 mol B 0.03 mol |
Conditions | Yield |
---|---|
With triethylaluminum; diethylaluminium hydride In hexane; kerosene for 25h; Heating; | 0.02 mol |
2-methyl-1,3-dioxolane
A
2-ethoxy-ethanol
B
ethanol
C
ethane
D
monoethylene glycol diethyl ether
E
acetic acid
F
ethyl acetate
Conditions | Yield |
---|---|
With hydrogen; Pt-Cab-O-Sil at 300℃; Product distribution; Mechanism; var. of catalyst, temp.; |
Conditions | Yield |
---|---|
With hydrogen; Pt on Cab-O-Sil at 200℃; Product distribution; Mechanism; var. of H2 coverage, temp.; |
2-ethoxyethyl nitrite
2-ethoxy-ethanol
Conditions | Yield |
---|---|
With 2,2-dimethyl-propanol-1 In chloroform at 26℃; Equilibrium constant; Mechanism; var. alcohols; | |
With hydrogenchloride; sodium perchlorate at 25℃; Rate constant; acetate buffer pH 2; | |
With tris-(2-chloro-ethyl)-amine In 1,4-dioxane; water at 25℃; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.), solvent isotope effect (kH/kD); |
sulfuric acid mono-(2-ethoxy-ethyl ester)
2-ethoxy-ethanol
Conditions | Yield |
---|---|
With sulfuric acid at 32.5℃; Equilibrium constant; |
ethylene glycol sec-butyl ethyl ether
A
1-butylene
B
2-ethoxy-ethanol
C
(Z)-2-Butene
D
trans-2-Butene
Conditions | Yield |
---|---|
KU-23 sulfonated cation-exchange resins at 130℃; Equilibrium constant; other temperature;; |
carbon monoxide
A
methanol
B
2-ethoxy-ethanol
C
2-methoxy-ethanol
D
ethylene glycol
Conditions | Yield |
---|---|
With hydrogen; rhodium(III) acetylacetonate; tris(2,4-pentanedionato)ruthenium(III); tetrabutyl phosphonium bromide at 220℃; under 326800 Torr; Further byproducts given; | A 250 mmol B n/a C n/a D 77.2 mmol |
2-ethoxyethyl nitrite
benzyl-methyl-amine
A
2-ethoxy-ethanol
B
Benzylmethylnitrosamin
Conditions | Yield |
---|---|
In 1,4-dioxane; water at 25℃; Rate constant; |
2-ethoxyethyl nitrite
3-hydroxy-dl-proline
A
2-ethoxy-ethanol
B
N-nitrosohydroxyproline
Conditions | Yield |
---|---|
In 1,4-dioxane; water at 25℃; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.), solvent isotope effect (kH/kD); |
piperazine
2-ethoxyethyl nitrite
A
2-ethoxy-ethanol
B
N-nitrosopiperazine
Conditions | Yield |
---|---|
With sodium docusate In 2,2,4-trimethylpentane; water Rate constant; |
2-ethoxyethyl nitrite
malononitrile
A
2-ethoxy-ethanol
B
2-(hydroxyimino)malononitrile
Conditions | Yield |
---|---|
With sodium hydroxide at 25℃; Rate constant; |
uridine 3'-(2-ethoxyethyl) phosphate
A
2-ethoxy-ethanol
B
uridine-3'-phosphate
Conditions | Yield |
---|---|
With zinc(II) nitrate; sodium nitrate at 90℃; pH=5.6; Kinetics; Hydrolysis; |
2-ethoxy-ethanol
p-toluenesulfonyl chloride
2-ethoxyethyl p-toluenesulfonate
Conditions | Yield |
---|---|
With pyridine at 0℃; | 100% |
With sodium hydroxide In tetrahydrofuran; water | 85% |
With triethylamine In dichloromethane at 20℃; for 4h; | 81.1% |
2-ethoxy-ethanol
N-(2,6-dimethylphenyl)alanine
2-ethoxyethyl N-(2,6-dimethylphenyl)alaninate
Conditions | Yield |
---|---|
With thionyl chloride | 100% |
2-ethoxy-ethanol
4-chloro-3-[(2-methanesulfonyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl)amino]benzoic acid methyl ester
4-Chloro-3-{[2-(2-ethoxy-ethoxy)-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl]-amino}-benzoic acid
Conditions | Yield |
---|---|
Stage #1: 2-ethoxy-ethanol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Stage #2: 4-chloro-3-[(2-methanesulfonyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl)amino]benzoic acid methyl ester In N,N-dimethyl-formamide; mineral oil at 20℃; for 18h; | 100% |
2-ethoxy-ethanol
methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropyridine-2-carboxylate
methyl 6-(4-(2-ethoxyethoxy)-2,6-difluorophenyl)-5-fluoropicolinate
Conditions | Yield |
---|---|
Stage #1: 2-ethoxy-ethanol With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropyridine-2-carboxylate In tetrahydrofuran | 100% |
Conditions | Yield |
---|---|
With dilithium tetra(tert-butyl)zincate In toluene at 0℃; for 1h; Inert atmosphere; | 100% |
2-ethoxy-ethanol
Conditions | Yield |
---|---|
In benzene byproducts: (CH3)2CHOH; performed in a moisture free environment; benzene soln. of Zr(acac)2(OiPr)2 added to a benzene suspension of the organic ligand; refluxed for 4h; solvent removed under reduced pressure; purified by recrystallization from a mixture of dichloromethane and n-hexane; elem. anal.; | 99% |
Conditions | Yield |
---|---|
In toluene under an inert atm.; to a soln. of TiCl4 (8.51 mmol) in toluene was added a toluene soln. of a ligand (8.51 mmol); stirring for 3 h; supernatant was decanted and the solid washed with petroleum spirits; the residue was dried under vac.; elem. anal.; | 99% |
2-ethoxy-ethanol
bis(N-phenylsalicylideneiminato)aluminium(III)di(μ-isopropoxo)di(isopropoxo) aluminium(III)
[(N-phenylsalicylideneiminato)2Al(III)(μ-O(i-Pr))2Al(III)(O(i-Pr))(OCH2CH2OC2H5)]
Conditions | Yield |
---|---|
In benzene byproducts: (CH3)2CHOH; under anhyd. conditions; mixt. was refluxed for 4 h, 1:1 molar ratio of Al complex and ligand; solvent was removed; elem. anal.; | 98.9% |
2-ethoxy-ethanol
cis-di-2-propanolato-bis(8-quinolinato)-titanium(IV)
2-methoxy-ethanol
Conditions | Yield |
---|---|
In toluene at 100 - 120℃; Reflux; | 98.3% |
2-ethoxy-ethanol
bis(N-phenylsalicylideneiminato)aluminium(III)di(μ-isopropoxo)di(isopropoxo) aluminium(III)
[(N-phenylsalicylideneiminato)2Al(III)(μ-O(i-Pr))2Al(III)(OCH2CH2OC2H5)2]
Conditions | Yield |
---|---|
In benzene byproducts: (CH3)2CHOH; under anhyd. conditions; mixt. was refluxed for 4 h, 1:2 molar ratio of Al complex and ligand; solvent was removed; elem. anal.; | 98.2% |
2-ethoxy-ethanol
cis-di-2-propanolato-bis(8-quinolinato)-titanium(IV)
1-(2-furyl)ethanone oxime
Conditions | Yield |
---|---|
In toluene at 100 - 120℃; | 98.2% |
2-ethoxy-ethanol
(Ap)Ti(OPri)2
1-(2-furyl)ethanone oxime
C18H21NO6Ti
Conditions | Yield |
---|---|
In toluene Reflux; | 98.1% |
2-ethoxy-ethanol
5,7,3',4'-tetra-O-benzyl-(+)-catechin
(2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2"-ethoxyethoxy)flavan-3-ol
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 98% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane | 98% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0 - 20℃; Inert atmosphere; | 85% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone |
Conditions | Yield |
---|---|
In water under 760.051 Torr; for 7h; Heating / reflux; | 98% |
titanium(IV) isopropylate
2-ethoxy-ethanol
tetrakis(2-ethoxyethanolato)titanium(IV)
Conditions | Yield |
---|---|
In benzene for 4h; Reflux; | 98% |
2-ethoxy-ethanol
Ricinoleic acid
ricinoleic acid ethylene glycol ethyl ether ester
Conditions | Yield |
---|---|
With sodium hydrogensulfate monohydrate In dichloromethane at 150℃; for 0.416667h; Microwave irradiation; High pressure; | 98% |
With toluene-4-sulfonic acid In cyclohexane for 5h; Time; Reagent/catalyst; Solvent; Reflux; |
Conditions | Yield |
---|---|
With tetrabutylammonium perchlorate In acetonitrile at 20℃; for 8h; Electrochemical reaction; | 98% |
2-hydroxypyridin
2-ethoxy-ethanol
cis-di-2-propanolato-bis(8-quinolinato)-titanium(IV)
Conditions | Yield |
---|---|
In toluene at 100 - 120℃; Reflux; | 97.9% |
2-ethoxy-ethanol
2-acetylthiophene oxime
cis-di-2-propanolato-bis(8-quinolinato)-titanium(IV)
Conditions | Yield |
---|---|
In toluene at 100 - 120℃; Reflux; | 97.9% |
2-ethoxy-ethanol
cis-di-2-propanolato-bis(8-quinolinato)-titanium(IV)
1-pyridin-2-yl-ethanone oxime
Conditions | Yield |
---|---|
In toluene at 100 - 120℃; | 97.9% |
2-ethoxy-ethanol
(Ap)Ti(OPri)2
1-pyridin-2-yl-ethanone oxime
C19H22N2O5Ti
Conditions | Yield |
---|---|
In toluene Reflux; | 97.6% |
2-ethoxy-ethanol
cis-di-2-propanolato-bis(8-quinolinato)-titanium(IV)
Conditions | Yield |
---|---|
In toluene at 100 - 120℃; Reflux; | 97.5% |
2-ethoxy-ethanol
1-chloro-2,4-dinitro-benzene
2,4-dinitro-1-(2-ethoxyethoxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In water | 97.4% |
Conditions | Yield |
---|---|
With sodium persulfate; sodium bis(1,2-dicarbollyl)cobaltate(III); potassium carbonate In water for 8h; pH=7; Irradiation; | 97% |
With sodium hydroxide; potassium hexacyanoferrate(III) at 30℃; Kinetics; Further Variations:; substrate and reagents concentration dependence; Oxidation; | |
With Jones reagent In acetone at 20℃; | |
With sodium hydroxide; cadmium(II) oxide at 225 - 250℃; im Kupferautoklaven; |
2-ethoxy-ethanol
5,7,3',4'-tetra-O-benzyl-(+)-catechin
(2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2-ethoxy-ethoxy)-chroman-3-ol
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 97% |
Conditions | Yield |
---|---|
In benzene for 4h; Reflux; | 97% |
2-ethoxy-ethanol
ethoxyacetaldehyde
Conditions | Yield |
---|---|
With Dess-Martin periodane In dichloromethane for 1h; Concentration; | 96.5% |
With bromamine T In hydrogenchloride at 45℃; Thermodynamic data; Rate constant; Mechanism; Ea, ΔH(excit.), ΔS(excit.), ΔG(excit.); | |
With pyridinium chlorochromate In dimethyl sulfoxide for 6h; Kinetics; Mechanism; Thermodynamic data; Εa, log A, ΔS(excit.), ΔG(excit.); |
2-ethoxy-ethanol
chloroacetic acid
chloro-acetic acid-(2-ethoxy-ethyl ester)
Conditions | Yield |
---|---|
F-4SK (H form) In toluene at 120℃; for 3h; | 96% |
With toluene |
2-ethoxy-ethanol
8-dioxane-3-cobalt-bis(1,2-dicarbollide)
sodium hydroxide
Conditions | Yield |
---|---|
In 2-ethoxy-ethanol (N2); stirring alcohol with NaOH for 45 min, addn. of cobalt complex, stirring at room temp. for 15 min; evapn., thin layer chromy. (silica gel, CH2Cl2/ethanol 9:1); elem. anal.; | 96% |
Conditions | Yield |
---|---|
With sodium In 2-ethoxy-ethanol; toluene N2, Na dissolved, CoCl2 added with vigorous stirring, refluxed for 40 min, left for 30 min at room temp.; soln. decanted, left overnight at -30°C, crysts. decanted, dried (vac.); | 96% |
Molecule structure of 2-Ethoxyethanol (CAS NO.110-80-5):
IUPAC Name: 2-Ethoxyethanol
Molecular Weight: 90.121 g/mol
Molecular Formula: C4H10O2
Density: 0.915 g/cm3
Melting Point: -100 °C
Boiling Point: 135.6 °C at 760 mmHg
Flash Point: 44.4 °C
Index of Refraction: 1.399
Molar Refractivity: 23.86 cm3
Molar Volume: 98.4 cm3
Surface Tension: 28.6 dyne/cm
Enthalpy of Vaporization: 39.22 kJ/mol
Vapour Pressure: 3.28 mmHg at 25 °C
storage temp.: flammables area
Water Solubility: miscible
XLogP3: -0.3
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 3
Exact Mass: 90.06808
MonoIsotopic Mass: 90.06808
Topological Polar Surface Area: 29.5
Heavy Atom Count: 6
Canonical SMILES: CCOCCO
InChI: InChI=1S/C4H10O2/c1-2-6-4-3-5/h5H,2-4H2,1H3
InChIKey: ZNQVEEAIQZEUHB-UHFFFAOYSA-N
EINECS: 203-804-1
Product Categories: Industrial/Fine Chemicals; Ethylene Glycols & Monofunctional Ethylene Glycols; Monofunctional Ethylene Glycols
2-Ethoxyethanol (CAS NO.110-80-5) is a solvent used widely in commercial and industrial applications.
2-Ethoxyethanol can be manufactured by the reaction of ethylene oxide with ethanol.
1. | eye-hmn 6000 ppm | PHRPA6 Public Health Reports. 45 (1930),1459. | ||
2. | skn-rbt 500 mg open MLD | UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 5/20 ,1966. | ||
3. | eye-rbt 500 mg/24H MLD | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,624. | ||
4. | eye-rbt 50 mg MOD | UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 5/20 ,1966. | ||
5. | eye-gpg 10 μg MLD | JPPMAB Journal of Pharmacy and Pharmacology. 11 (1959),150. | ||
6. | orl-rat LD50:2125 mg/kg | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 32 (3)(1988),48. | ||
7. | ihl-rat LC50:2000 ppm/7H | NPIRI* Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. 1 (1974),54. | ||
8. | skn-rat LD50:3900 mg/kg | TOXID9 Toxicologist. 4 (1984),180. | ||
9. | ipr-rat LD50:2800 mg/kg | ARZNAD Arzneimittel-Forschung. Drug Research. 21 (1971),880. | ||
10. |
|
Reported in EPA TSCA Inventory. Glycol ether compounds are on the Community Right-To-Know List.
Hazard Codes: T
Risk Statements: 60-61-10-20/21/22
R60:May impair fertility.
R61:May cause harm to the unborn child.
R10:Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 53-45
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 1171 3/PG 3
WGK Germany: 1
RTECS: KK8050000
HazardClass: 3
PackingGroup: III
Moderately toxic by ingestion, skin contact, intravenous, and intraperitoneal routes. Mildly toxic by inhalation and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. A mild eye and skin irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. Moderate explosion hazard in the form of vapor when exposed to heat or flame. Mixture with hydrogen peroxide + polyacrylamide gel + toluene is explosive when dry. To fight fire, use alcohol foam, dry chemical. See also GLYCOL ETHERS.
OSHA PEL: TWA 200 ppm (skin)
ACGIH TLV: TWA 5 ppm (skin); BEI: 100 mg/g creatinine of 2-ethoxyacetic acid in urine end of shift at end of workweek
DFG MAK: 5 ppm (19 mg/m3)
NIOSH REL: (Glycol Ethers) Reduce to lowest level
DOT Classification: 3; Label: Flammable Liquid
For occupational chemical analysis use OSHA: #53 or NIOSH: Alcohols IV, 1403.
2-Ethoxyethanol (CAS NO.110-80-5) is also named as 2-Ethoxyethyl alcohol ; AI3-01236 ; Athylenglykol-monoathylather ; Athylenglykol-monoathylather [German] ; Bikanol E 1 ; CCRIS 2294 ; Cellosolve ; Cellosolve solvent ; Celosolv ; Celosolv [Czech] ; Dowanol 8 ; Dowanol EE ; EGEE ; Ektasolve EE ; Emkanol ; Eter monoetilico del etilenglicol ; Eter monoetilico del etilenglicol [Spanish] ; Ethanol, 2-ethoxy- ; Ether monoethylique de l'ethylene-glycol ; Ether monoethylique de l'ethylene-glycol [French] ; Ethyl cellosolve ; Ethyl ethylene glycol ; Ethylene glycol ethyl ether ; Ethylene glycol monoethyl ether ; Ethylethylene glycol ; Etoksyetylowy alkohol ; Etoksyetylowy alkohol [Polish] ; Glycol monoethyl ether ; HSDB 54 ; Hydroxy ether ; Jeffersol EE ; NCI-C54853 ; NSC 8837 ; Oxitol ; Plastiazan 60 ; Poly-Solv EE ; RCRA waste number U227 ; RCRA waste number U359 ; Solvid ; Solvulose ; UNII-IDK7C2HS09 ; beta-Ethoxyethanol . 2-Ethoxyethanol (CAS NO.110-80-5) is a clear, colorless, nearly odorless liquid that is miscible with water, ethanol, diethyl ether, acetone, and ethyl acetate. It is flammable. 2-Ethoxyethanol (CAS NO.110-80-5) may react with oxidizing materials, i.e. hydrogen peroxide, to form peroxides. It dissolves many oils, resins and waxes. Some eye irritation. Inhalation of vapors causes irritation of nose. Toxic gases, such as carbon monoxide, may be produced in fire.
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