Conditions | Yield |
---|---|
With hydrogen In 2-methyltetrahydrofuran; water at 40℃; under 15001.5 Torr; for 24h; chemoselective reaction; | 99% |
With sodium sulfide; tetrabutylammomium bromide In water; toluene at 80℃; for 0.75h; Zinin reduction; | 98.4% |
With hydrogen; triethylamine In ethanol; water at 110℃; under 30003 Torr; for 24h; Autoclave; | 96% |
4,4'-diethoxyazoxybenzene
4-Ethoxyaniline
Conditions | Yield |
---|---|
With N-doped TiO2 In methanol at 20℃; for 3h; UV-irradiation; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With sodium hydroxide; dimethyl sulfoxide | 90.1% |
N-allyl-p-phenetidine
4-Ethoxyaniline
Conditions | Yield |
---|---|
With polymethylhydrosiloxane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; | 88% |
Conditions | Yield |
---|---|
With hemicucurbituril supported [Bmim]Cl In toluene for 10h; Reflux; | 80% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 24h; | 78% |
With sodium hydride In acetonitrile at 20℃; for 24h; |
Conditions | Yield |
---|---|
With hemicucurbituril supported [Bmim]Cl In toluene for 9h; Reflux; | 75% |
Conditions | Yield |
---|---|
With hemicucurbituril supported [Bmim]Cl In toluene for 10h; Reflux; | 75% |
chloroethane
diethylene glycol dimethyl ether
4-amino-phenol
2-methoxy-phenylamine
4-Ethoxyaniline
Conditions | Yield |
---|---|
With sodium methylate In methanol | 72.1% |
3-Benzyl-2-[(Z)-4-ethoxy-phenylimino]-6-methyl-2,3-dihydro-6H-thiazolo[4,5-d]pyridazin-7-one
A
2-Oxothiazolo<4,5-d>pyridazin-7(6H)-one
B
4-Ethoxyaniline
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 48h; Heating; | A 62% B n/a |
Conditions | Yield |
---|---|
With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide In 2,2,2-trifluoroethanol; water at 30℃; for 2h; | A 51.5% B 24.5% |
Conditions | Yield |
---|---|
With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide In 2,2,2-trifluoroethanol; water at 30℃; for 2h; Reagent/catalyst; Solvent; | A 30.4% B 45.6% |
1-methyl-6-(4'-ethoxyphenyl)-2,5-dithiobiurea
A
2-(4'-ethoxyphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione
B
4-Ethoxyaniline
C
methylamine
D
4-methyl-[1,2,4]triazolidine-3,5-dithione
Conditions | Yield |
---|---|
With sodium hydroxide In water Heating; | A 41% B n/a C n/a D 32% |
1-ethyl-6-(4'-ethoxyphenyl)-2,5-dithiobiurea
A
2-(4'-ethoxyphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione
B
ethylamine
C
4-Ethoxyaniline
D
4-ethyl-[1,2,4]triazolidine-3,5-dithione
Conditions | Yield |
---|---|
With sodium hydroxide In water Heating; | A 41% B n/a C n/a D 32% |
2-[(E)-4-Ethoxy-phenylimino]-3,5-dimethyl-3,5-dihydro-2H-thiazolo[4,5-d]pyridazin-4-one
A
3,5-Dimethyl-3,5-dihydro-thiazolo[4,5-d]pyridazine-2,4-dione
B
4-Ethoxyaniline
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 48h; Heating; | A 41% B n/a |
Conditions | Yield |
---|---|
Stage #1: 4-amino-phenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 20℃; for 20h; Further stages.; | 36% |
Conditions | Yield |
---|---|
at 120℃; Reflux; | 17% |
Conditions | Yield |
---|---|
With sodium hydroxide; ethanol at 100℃; und Erhitzen des entstandenen Benzal-p-phenetidins mit ueberschuessiger Salzsaeure oder Schwefelsaeure; |
Conditions | Yield |
---|---|
With diethyl ether; ammonia; potassium amide | |
With ammonia; potassium amide; Petroleum ether | |
With copper(I) oxide; ammonia; water at 225℃; |
(4-ethoxy-phenyl)-amidosulfuric acid
4-Ethoxyaniline
Conditions | Yield |
---|---|
With potassium hydroxide |
A
(1R,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
B
4-Ethoxyaniline
Conditions | Yield |
---|---|
3-<4-ethoxy-anilino>-3-hydroxylamino-d-camphor; |
Conditions | Yield |
---|---|
at 270℃; |
(4-ethoxy-phenyl)-carbamic acid benzyl ester
4-Ethoxyaniline
Conditions | Yield |
---|---|
With hydrogenchloride; palladium Hydrogenation; |
Conditions | Yield |
---|---|
Reduktion; |
Conditions | Yield |
---|---|
With sulfuric acid; magnesium |
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol; magnesium |
urea
N,N'-bis-(4-ethoxy-phenyl)-urea
butan-1-ol
A
N-(p-ethoxyphenyl)urea
C
4-Ethoxyaniline
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
With nickel at 200℃; under 25742.8 Torr; Hydrogenation; | |
With iron; acetic acid | |
With hydrogenchloride; tin | |
With manganese oxide; nickel(II) carbonate; basic copper carbonate powder at 180℃; under 7600 Torr; Hydrogenation.Reagens 4: Decalin; |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 120℃; for 16h; | 100% |
With ethanol |
Conditions | Yield |
---|---|
With aluminum oxide for 5h; Milling; | 100% |
In ethanol for 1h; Sonication; | 100% |
With magnesium sulfate; acetic acid In dichloromethane at 20℃; for 18h; Inert atmosphere; | 73% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.166667h; | 100% |
With diethyl ether |
3,4-dimethoxy-benzaldehyde
4-Ethoxyaniline
(3,4-dimethoxybenzylidene)(4-ethoxyphenyl)amine
Conditions | Yield |
---|---|
In toluene Heating; | 100% |
In ethanol Heating; | 94% |
at 110℃; |
Conditions | Yield |
---|---|
With acetic acid at 20℃; for 3h; | 100% |
With acetic acid In water at 20℃; for 3h; | 100% |
With acetic acid at 20℃; |
chloroform
4-Ethoxyaniline
acetone
α-p-phenetidino-isobutyric acid p-phenetidide
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 5℃; | 100% |
di-tert-butyl dicarbonate
4-Ethoxyaniline
N-(tert-butoxycarbonyl)-4-ethoxyaniline
Conditions | Yield |
---|---|
With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.1h; | 100% |
In tetrahydrofuran for 2.5h; Heating; | 98% |
With pyridinium trifluroacetate In neat (no solvent) at 20℃; for 0.0166667h; Green chemistry; | 93% |
Conditions | Yield |
---|---|
In benzene at 5℃; for 0.166667h; | 100% |
Conditions | Yield |
---|---|
Stage #1: benzaldehyde; 4-Ethoxyaniline With magnesium sulfate In acetonitrile at 20℃; for 2h; Stage #2: bis(p-methoxyphenyl)methylenecyclopropane; Montmorillonite KSF In acetonitrile at 20℃; for 48h; aza-Diels-Alder reaction; Further stages.; | 100% |
Conditions | Yield |
---|---|
Stage #1: 4-Ethoxyaniline With hydrogenchloride In water; acetone at 20℃; for 0.5h; Stage #2: With sodium nitrite In water; acetone at 0℃; for 0.5h; Stage #3: phenol With sodium carbonate; sodium hydroxide In water; acetone at 0℃; for 1h; | 100% |
Stage #1: 4-Ethoxyaniline With hydrogenchloride; sodium nitrite In ethanol; water at 0℃; for 1h; Stage #2: phenol With sodium hydroxide In ethanol; water at 5℃; for 1.5h; | 76% |
Stage #1: 4-Ethoxyaniline With hydrogenchloride; sodium nitrite In ethanol; water Cooling with ice; Stage #2: phenol With sodium hydroxide In ethanol; water for 1.5h; pH=1; Cooling; |
Conditions | Yield |
---|---|
In ethanol for 1h; Sonication; | 100% |
Conditions | Yield |
---|---|
In benzene at 5℃; for 0.166667h; | 99.9% |
Conditions | Yield |
---|---|
With hydrogen; potassium hydroxide; silver(l) oxide In methanol at 125℃; under 26252.6 Torr; for 4h; Concentration; Autoclave; | 99.4% |
With hydrogenchloride |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 25℃; for 12h; | 99% |
With sodium hydroxide; chloroform |
1-benzyl-6-chloroindolin-2,3-dione
2-isopropenylphenol
4-Ethoxyaniline
1-benzyl-6-chloro-6'-ethoxy-4'-(2-hydroxyphenyl)-4'-methyl-3',4'-dihydro-1'H-spiro[indoline-3,2'-quinolin]-2-one
Conditions | Yield |
---|---|
With (R)-3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate In toluene at -20℃; Molecular sieve; enantioselective reaction; | 99% |
4-Ethoxyaniline
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; butan-1-ol at 120℃; for 0.666667h; Microwave irradiation; | 99% |
4-Ethoxyaniline
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-((4-chlorobenzyl)oxy)benzaldehyde; 4-Ethoxyaniline With acetic acid In methanol at 20℃; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol Inert atmosphere; | 98.1% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 98% |
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 0 - 20℃; for 4h; | 98% |
With toluene | |
With tetralin |
4-Ethoxyaniline
6-chloro-2-iodo-9-isopropyl-9H-purine
Conditions | Yield |
---|---|
With triethylamine In ethanol at 50℃; Substitution; | 98% |
Conditions | Yield |
---|---|
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane for 24h; Heating; | 98% |
2-chloro-1,4-dimethyl-benzene
4-Ethoxyaniline
N-(4-ethoxyphenyl)-2,5-dimethylaniline
Conditions | Yield |
---|---|
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate In dibutyl ether; toluene at 110℃; for 1h; Inert atmosphere; | 98% |
With sodium t-butanolate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; C8H10ClNPd In dibutyl ether at 110℃; for 1h; Product distribution / selectivity; Inert atmosphere; | 98% |
pyridinium trifluroacetate
4-Ethoxyaniline
N-(4-ethoxyphenyl)-2,2,2-trifluoroacetamide
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene for 2h; Reflux; | 98% |
2-chloronicotinic acid
4-Ethoxyaniline
2-[(4-ethoxyphenyl)amino]pyridine-3-carboxylic acid
Conditions | Yield |
---|---|
With potassium carbonate In water at 150℃; for 1.5h; Green chemistry; | 98% |
With potassium carbonate In water at 150℃; for 1h; Microwave irradiation; | 86% |
ethyl 2-(2-oxo-2-phenylethoxy)-4,5,6,7-tetrahydro-[1]-benzothiophene-3-carboxylate
4-Ethoxyaniline
C25H23NO3S
Conditions | Yield |
---|---|
In acetic anhydride; acetic acid for 18h; Reflux; | 98% |
5-ethoxycarbonyl-2,6-dimethyl-3-pyridinecarboxylic acid azide
4-Ethoxyaniline
C19H23N3O4
Conditions | Yield |
---|---|
In benzene for 1h; Reflux; | 98% |
Conditions | Yield |
---|---|
With calcium(II) bis(trifluoromethanesulfonyl)imide In neat (no solvent) at 115℃; for 1h; Reagent/catalyst; Microwave irradiation; Sealed tube; | 98% |
N,N-dimethyl-formamide dimethyl acetal
4-Ethoxyaniline
Ε-N'-(4-ethoxyphenyl)-N,N-dimethylformamidine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5h; Concentration; Solvent; | 98% |
The molecular structure of Phenetidine (CAS NO.156-43-4):
IUPAC Name: 4-Ethoxyaniline
Molecular Weight: 137.17904 g/mol
Molecular Formula: C8H11NO
Density: 1.037 g/cm3
Melting Point: 2-5 °C(lit.)
Boiling Point: 254 °C at 760 mmHg
Flash Point: 110.3 °C
Index of Refraction: 1.544
Molar Refractivity: 41.8 cm3
Molar Volume: 132.2 cm3
Surface Tension: 38.5 dyne/cm
Enthalpy of Vaporization: 49.14 kJ/mol
Vapour Pressure: 0.0177 mmHg at 25 °C
Water Solubility: practically insoluble
Sensitive: air sensitive
XLogP3: 1.2
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Exact Mass: 137.084064
MonoIsotopic Mass: 137.084064
Topological Polar Surface Area: 35.2
Heavy Atom Count: 10
Canonical SMILES: CCOC1=CC=C(C=C1)N
InChI: InChI=1S/C8H11NO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2,9H2,1H3
InChIKey: IMPPGHMHELILKG-UHFFFAOYSA-N
EINECS: 205-855-5
Product Categories: INORGANIC & ORGANIC CHEMICALS; Phenetole; Anilines (Building Blocks for Liquid Crystals); Building Blocks for Liquid Crystals; Functional Materials
Phenetidine (CAS NO.156-43-4) is used as intermediates of medicine, dyes, food preservatives, feed additives and rubber antioxidant.
1. | skn-rbt 500 mg MLD | FCTOD7 Food and Chemical Toxicology. 20 (1982),563. | ||
2. | eye-rbt 100 mg MOD | FCTOD7 Food and Chemical Toxicology. 20 (1982),563. | ||
3. | eye-rbt 100 mg/45 rns MLD | FCTOD7 Food and Chemical Toxicology. 20 (1982),563. | ||
4. | mma-sat 1 µmol/plate | CPBTAL Chemical and Pharmaceutical Bulletin. 33 (1985),2877. | ||
5. | dni-ham:lng 160 µmol/L | MUTAEX Mutagenesis. 3 (1988),51. | ||
6. | orl-rat LD50:580 mg/kg | GISAAA Gigiena i Sanitariya. 35 (8)(1970),28. | ||
7. | ihl-rat LCLo:250 mg/m3 | GISAAA Gigiena i Sanitariya. 35 (8)(1970),28. | ||
8. | orl-mus LD50:530 mg/kg | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 25 (8)(1981),50. | ||
9. | ipr-mus LD50:692 mg/kg | JMCMAR Journal of Medicinal Chemistry. 17 (1974),900. |
Reported in EPA TSCA Inventory.
Hazard Codes: T, Xi, Xn
Risk Statements: 23/24/25-33-68-43-36-20/21/22
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R33:Danger of cumulative effects.
R68:Possible risk of irreversible effects.
R43:May cause sensitization by skin contact.
R36:Irritating to eyes.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 28-36/37-45-46
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S46:If swallowed, seek medical advice immediately and show this container or label.
RIDADR: UN 2311 6.1/PG 3
WGK Germany: 1
RTECS: SI6465500
F: 8-10
Hazard Note: Irritant
HazardClass: 6.1
PackingGroup: III
HS Code: 29222200
Poison by inhalation. Moderately toxic by ingestion and intraperitoneal routes. Caution: It can be absorbed through the skin. A skin and eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Phenetidine (CAS NO.156-43-4) is also named as 1-Amino-4-ethoxybenzene ; 4-13-00-01017 (Beilstein Handbook Reference) ; 4-Aminoethoxybenzene ; 4-Aminophenetole ; 4-Ethoxyaniline ; 4-Ethoxybenzenamine ; AI3-09042 ; Aniline, p-ethoxy- ; BRN 0606666 ; CCRIS 2878 ; CP 5685 ; NSC 3116 ; p-Aminofenetol ; p-Aminofenetol [Czech] ; p-Aminophenetole ; p-Ethoxyaniline ; p-Fenetidin ; p-Fenetidin [Czech] ; p-Phenetidin ; p-Phenetidine . Phenetidine (CAS NO.156-43-4) is colourless liquid. It is slightly soluble in water. It is very sensitive to exposure to air and light. It can turn red to brown on exposure to light and air. Phenetidine reacts vigorously with powerful oxidizers. It is combustible.
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