Conditions | Yield |
---|---|
With potassium carbonate at 180℃; for 2h; Autoclave; | 100% |
With Magnesium-Aluminum layered double oxides catalyst at 149.84℃; under 760.051 Torr; for 12h; Autoclave; Inert atmosphere; Irradiation; Green chemistry; | 91% |
With N,N'-dimethylimidazolium-2-carboxylate In acetonitrile at 170℃; for 1.33333h; Temperature; Microwave irradiation; Green chemistry; | 90 %Spectr. |
Conditions | Yield |
---|---|
With sodium hydroxide; N-butyl-N,N-dimethyl-(α-phenyl)ethylammonium bromide In 1,2-dichloro-ethane for 6h; Heating; | 99% |
With potassium carbonate at 60℃; for 5h; Williamson synthesis; | 87% |
3-Dimethylamino-1-propanol
Diethyl carbonate
phenol
A
N,N-dimethyl-3-phenoxypropan-1-amine
B
Phenetole
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 200℃; for 8h; Autoclave; | A 99% B n/a |
Conditions | Yield |
---|---|
With potassium hydroxide; DCH-18-crown-6 immobilized on 2-vinylpyridine-styrene copolymer In chloroform for 6h; Heating; | 97% |
With 1-butyl-3-methylimidazolium hydroxide at 70℃; for 2h; | 80% |
With sodium hydride In tetrahydrofuran for 16h; | 60% |
Conditions | Yield |
---|---|
With 1,1,2,2-tetraphenyldisilane; azobisisobutyronitrile In ethanol for 14h; Heating; | 97% |
With 2,2'-azobis(isobutyronitrile); 1,1,2,2-tetraphenyldisilane In ethanol for 14h; Product distribution; Heating; other reagent, various amounts of initiator; | 97% |
With cetyltrimethylammonium bromide micelle; zinc In water Heating; | 85% |
diethyl ether
2-methoxy-1,3-dimethylbenzene
benzylium cation
A
1,3-Dimethyl-2-(phenylmethoxy)benzene
B
Phenetole
Conditions | Yield |
---|---|
at 25℃; Product distribution; Mechanism; nuclear decay of tritium atom; | A 3% B 94% C n/a |
Phenetole
Conditions | Yield |
---|---|
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 12h; Glovebox; | 94% |
Conditions | Yield |
---|---|
With oxygen In ethanol at 80℃; for 0.5h; | 93% |
With trimethylsilyl trifluoromethanesulfonate In ethanol 1) 1 h, 0 deg C 2) 1 h, r.t.; | 82 % Chromat. |
With trimethylsilyl trifluoromethanesulfonate In ethanol Product distribution; 1) 1 h, 0 deg C 2) 1 h, r.t., other solvent or with AgOTf; other α,β-unsaturated cyclohexenones: dehydrogenative aromatization; | 82 % Chromat. |
Conditions | Yield |
---|---|
With Triethoxysilane; C20H24N4Ni; sodium t-butanolate In toluene at 80℃; for 5h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique; | 91% |
With C22H28IrN2O2(1+)*CF3O3S(1-) In [D3]acetonitrile at 25℃; for 0.333333h; UV-irradiation; | 24% |
With air; triethyl borane; bis[4-(2-methoxyethoxy)phenyl]silane In tetrahydrofuran; ethanol at 20℃; for 4h; Reduction; | 6% |
Conditions | Yield |
---|---|
With 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In acetone Reflux; | 90% |
2-(Diethylamino)ethanol
Diethyl carbonate
phenol
A
N,N-diethyl-2-phenoxyaminoethane
B
Phenetole
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 200℃; for 8h; Autoclave; | A 90% B n/a |
2-(morpholin-4-yl)ethanol
Diethyl carbonate
phenol
A
4-(2-phenoxyethyl)morpholine
B
Phenetole
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 200℃; for 8h; Autoclave; | A 90% B n/a |
methanesulfonic acid p-phenetidide
Phenetole
Conditions | Yield |
---|---|
With chloroamine; sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; | 86% |
Conditions | Yield |
---|---|
at 120℃; for 4h; | 84.8% |
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 20℃; for 10h; | 84.3% |
With iron(III) hydroxide; sodium carbonate; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Sealed tube; | 73% |
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 5h; | 70% |
Conditions | Yield |
---|---|
With 2,6-dimethyl-1,4-benzoquinone In dichloromethane at 20℃; for 0.5h; | 84% |
Conditions | Yield |
---|---|
With hemicucurbituril supported [Bmim]Cl In toluene for 9h; Reflux; | 84% |
Conditions | Yield |
---|---|
With Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate In isopropyl alcohol at 80℃; for 5h; Ullmann Condensation; | 82% |
With caesium carbonate In toluene at 120℃; for 24h; Ullmann Condensation; Sealed tube; | 75% |
With potassium phosphate; copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione at 130℃; for 30h; Inert atmosphere; Sealed tube; chemoselective reaction; | 97 %Chromat. |
Conditions | Yield |
---|---|
With hemicucurbituril supported [Bmim]Cl In toluene for 9h; Reagent/catalyst; Solvent; Reflux; | 82% |
1-iodo-2-phenoxy-ethane
Phenetole
Conditions | Yield |
---|---|
With air; triethyl borane; bis[4-(2-methoxyethoxy)phenyl]silane In tetrahydrofuran; ethanol at 20℃; for 4h; Reduction; | 81% |
Conditions | Yield |
---|---|
With hemicucurbituril supported [Bmim]Cl In toluene for 9h; Reflux; | 80% |
1-piperidinoethanol
Diethyl carbonate
phenol
A
Phenetole
B
1-(2-phenoxyethyl)piperidine
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 200℃; for 8h; Autoclave; | A n/a B 79% |
1-pyrrolidineethanol
Diethyl carbonate
phenol
A
1-(2-phenoxyethyl)pyrrolidine
B
Phenetole
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 200℃; for 8h; Autoclave; | A 75% B n/a |
ethyl 2-methoxyethyl carbonate
phenol
A
2-methoxyethyl phenyl ether
B
Phenetole
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 180℃; for 24h; Autoclave; | A 28% B 72% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium hydroxide at 70℃; for 2h; | A 4 % Chromat. B 70% |
Conditions | Yield |
---|---|
With tetrafluoroboric acid dimethyl ether complex In pentane for 0.5h; | 70% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 1h; Heating; | 67% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium hydroxide at 70℃; for 2h; | A 4 % Chromat. B 65% |
Diethyl carbonate
phenol
A
bis(phenyl) carbonate
B
ethyl phenyl carbonate
C
Phenetole
Conditions | Yield |
---|---|
at 169.99 - 172.212℃; for 122.917h; Product distribution / selectivity; | A 1.52% B 63.1% C n/a |
at 171.101℃; for 97.3333 - 268h; Product distribution / selectivity; | A 1.4% B 37.6% C n/a |
Conditions | Yield |
---|---|
With aluminum oxide; sodium chlorite; (salen)Mn(III) In dichloromethane at 25℃; for 0.5h; | 100% |
With kaolin; sodium chlorite; manganese(III) acetylacetonate In dichloromethane at 25℃; for 1h; | 96% |
With N-chloro-succinimide; 2,4,6-trimethylaniline In dichloromethane at 20℃; Inert atmosphere; regioselective reaction; | 96% |
Phenetole
4-aminofuroxan-3-carboxylic acid azide
3-azidocarbonyl-4-(4-ethoxyphenylazo)furoxan
Conditions | Yield |
---|---|
Stage #1: 4-aminofuroxan-3-carboxylic acid azide With phosphoric acid; sulfuric acid; sodium nitrite at 0 - 2℃; for 1h; Stage #2: Phenetole In pyridine at 0 - 20℃; | 100% |
2-chloro-5-iodobenzoylchloride
Phenetole
(2-chloro-5-iodo-phenyl)-(4-ethoxyphenyl)methanone
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -7 - 9℃; for 2.33333h; | 98.5% |
With aluminum (III) chloride In dichloromethane at 5 - 15℃; for 2h; Friedel-Crafts Acylation; Industrial scale; regioselective reaction; | 88% |
Stage #1: 2-chloro-5-iodobenzoylchloride With aluminum (III) chloride In dichloromethane at 15 - 25℃; for 1h; Inert atmosphere; Stage #2: Phenetole In dichloromethane at -5 - 20℃; for 6h; | 72% |
Conditions | Yield |
---|---|
With sodium chlorite; Montmorillonite K10; manganese(III) acetylacetonate; sodium bromide In dichloromethane at 25℃; for 1h; | 98% |
With N-Bromosuccinimide; Montmorillonite at 30℃; Bromination; Heating; | 97% |
With iodobenzene; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium bromide In tetrahydrofuran; water at 20℃; for 1h; regioselective reaction; | 97% |
Conditions | Yield |
---|---|
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 3h; stereoselective reaction; | 98% |
Phenetole
4-dichloroiodanyl-phenetole
Conditions | Yield |
---|---|
Stage #1: Phenetole With chromium(VI) oxide; sulfuric acid; iodine In acetic anhydride; acetic acid at 20℃; Stage #2: With chromium(VI) oxide; hydrogenchloride; water In acetic anhydride; acetic acid at 20℃; for 1h; | 97.5% |
Conditions | Yield |
---|---|
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 2h; Ambient temperature; | 97% |
With lead(II,IV) oxide; iodine; acetic anhydride; acetic acid at 45℃; | 94% |
With phenyltrimethylammonium dichloroiodate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate for 0.45h; microwave irradiation; | 92% |
1,1'-sulfinylbisbenzene
Phenetole
diphenyl(4-ethoxyphenyl)sulfonium hexafluorophosphate
Conditions | Yield |
---|---|
Stage #1: 1,1'-sulfinylbisbenzene; Phenetole With aluminum (III) chloride; methanesulfonic acid; sulfuric acid at 5 - 15℃; for 5h; Stage #2: With potassium hexafluorophosphate In water; chlorobenzene at 25 - 40℃; for 1h; | 97% |
With potassium hexafluorophosphate; methanesulfonic acid; phosphorus pentoxide 2) water; Yield given. Multistep reaction; |
chromium(0) hexacarbonyl
Phenetole
(η6-ethoxybenzene)tricarbonylchromium
Conditions | Yield |
---|---|
In tetrahydrofuran; dibutyl ether for 48h; Heating; | 97% |
boiling;; | |
boiling;; |
Phenetole
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 24h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With VNU-1 In nitrobenzene at 120℃; for 0.0833333h; Friedel-Crafts Acylation; Microwave irradiation; | 96% |
With bismuth(lll) trifluoromethanesulfonate In neat (no solvent) at 100℃; for 0.166667h; Friedel-Crafts Acylation; Sealed tube; Microwave irradiation; | 92% |
With iron(III) sulfate In hexane at 20℃; for 0.583333h; Friedel-Crafts acylation; Sonication; | 86% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium nitrite; boric acid for 0.0291667h; Microwave irradiation; Neat (no solvent); regioselective reaction; | 96% |
With hydrogenchloride In water at 0 - 5℃; for 1h; regioselective reaction; | 95% |
With nitrosonium ethyl sulfate In dichloromethane at -40 - -35℃; for 0.333333h; Nitrosation; | 30% |
Conditions | Yield |
---|---|
Stage #1: di(p-tolyl) sulfoxide; Phenetole With aluminum (III) chloride; methanesulfonic acid; sulfuric acid at 5 - 15℃; for 6h; Stage #2: With potassium hexafluorophosphate In water; chlorobenzene at 25 - 35℃; for 1h; | 96% |
2-bromo-2-methylpropionyl chloride
Phenetole
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -10 - 10℃; for 1h; Inert atmosphere; | 95.2% |
Conditions | Yield |
---|---|
antimonypentachloride; N-benzyl-N,N,N-triethylammonium chloride In nitromethane for 0.333333h; Friedel-Crafts acylation; Heating; | 95% |
With carbon disulfide; aluminium trichloride | |
With aluminium trichloride |
Conditions | Yield |
---|---|
With aluminium trichloride In hexane for 0.75h; Ambient temperature; | 92% |
Conditions | Yield |
---|---|
With tetrabutylammonium acetate for 4.5h; Electrolysis; Inert atmosphere; Sealed tube; regioselective reaction; | 92% |
5-bromo-2-chloro-benzoyl chloride
Phenetole
(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-chloro-benzoyl chloride With tert-butyldimethylsilyl chloride In dichloromethane at 0 - 10℃; for 0.5h; Inert atmosphere; Stage #2: Phenetole With iron(III) chloride In dichloromethane at 0 - 10℃; for 5h; Time; Reagent/catalyst; Inert atmosphere; | 91.4% |
Stage #1: Phenetole In dichloromethane at 20℃; for 2h; Acidic conditions; Stage #2: 5-bromo-2-chloro-benzoyl chloride In dichloromethane at 30℃; for 4h; | 90% |
Stage #1: Phenetole With indium(III) chloride; iron(III) chloride In dichloromethane at -5℃; for 0.5h; Stage #2: 5-bromo-2-chloro-benzoyl chloride In dichloromethane at 0 - 10℃; for 3h; Time; Reagent/catalyst; | 90.6% |
Conditions | Yield |
---|---|
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In cyclohexane for 1h; Heating; | 90% |
With water; hydrogen bromide; Aliquat 336 at 105℃; for 7.5h; Catalytic behavior; | 90% |
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave; | 82% |
With tetrachlorosilane; sodium iodide In toluene; acetonitrile for 20h; Heating; | 59% |
With hydrogen In cis/trans-decahydronaphthalene at 350℃; under 30003 Torr; for 3h; Autoclave; | 6.7 %Chromat. |
Conditions | Yield |
---|---|
In water react. of t-BuC6H4SH dissolved in xylene with aq. soln. of AuCl(EtSC2H4OH); recrystn. from ethoxybenzene; | 90% |
The Phenetole, with the CAS registry number 103-73-1 and EINECS registry number 203-139-7, has the systematic name and IUPAC name of ethoxybenzene. It is also called Ethyl phenyl ether. And the molecular formula of this chemical is C8H10O. It is a kind of clear colourless to very slightly yellow liquid, and has the same properties as some other ethers, such as volatility, explosive vapors, and the ability to form peroxides. What's more, while dealing with this chemical, you should avoid contacting with skin and eyes.
The physical properties of Phenetole are as following: (1)ACD/LogP: 2.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.67; (4)ACD/LogD (pH 7.4): 2.67; (5)ACD/BCF (pH 5.5): 62.43; (6)ACD/BCF (pH 7.4): 62.43; (7)ACD/KOC (pH 5.5): 671.06; (8)ACD/KOC (pH 7.4): 671.06; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.489; (14)Molar Refractivity: 37.56 cm3; (15)Molar Volume: 129.9 cm3; (16)Polarizability: 14.89×10-24cm3; (17)Surface Tension: 29.8 dyne/cm; (18)Density: 0.94 g/cm3; (19)Flash Point: 55 °C; (20)Enthalpy of Vaporization: 38.96 kJ/mol; (21)Boiling Point: 169.8 °C at 760 mmHg; (22)Vapour Pressure: 2.01 mmHg at 25°C.
Preparation and uses of Phenetole: It can be prepared by Phenol sodium and ethyl bromide. Dissolve phenol in the sodium alkoxide solution, and cool down to below 20°C. Add ethyl bromide slowly, and reflux for 3 hours. Recycle the ethanol and filter to wipe off the generated sodium bromide, and you can get the crude product. In addition, Phenetole is usually used in the organic, and also used for the determination of aromatic orthophosphorous acid.
You can still convert the following datas into molecular structure:
(1)SMILES: O(c1ccccc1)CC
(2)InChI: InChI=1/C8H10O/c1-2-9-8-6-4-3-5-7-8/h3-7H,2H2,1H3
(3)InChIKey: DLRJIFUOBPOJNS-UHFFFAOYAS
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | oral | 3gm/kg (3000mg/kg) | "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2A, Pg. 2526, 1981. | |
mouse | LD50 | oral | 2200mg/kg (2200mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT | Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 400, 1946. |
rat | LDLo | subcutaneous | 3500mg/kg (3500mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: TREMOR LIVER: FATTY LIVER DEGERATION | Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895. |
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