Conditions | Yield |
---|---|
With hydrogen; aluminum oxide; silica gel; nickel In methanol; ammonia at 120℃; under 7600 Torr; for 6h; | 100% |
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h; | 100% |
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); potassium tert-butylate; hydrogen bromide; hydrogen; 2-((di-iso-propylphosphino)methyl)-1-methyl-1H-imidazole In tetrahydrofuran; water; acetone; toluene at 20℃; under 37503.8 Torr; for 5.5h; Inert atmosphere; Schlenk technique; Autoclave; | 98% |
2-[(4-methoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With hydrazine hydrate In tetrahydrofuran for 16h; Reflux; | 99% |
With hydrazine hydrate In 1,4-dioxane at 110℃; Gabriel Amine Synthesis; Inert atmosphere; | 90% |
With sodium hydroxide und anschliessend mit verd.Salzsaeure; |
p-methoxyl benzaldoxime
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With sodium tetrahydroborate at 20℃; for 0.0333333h; neat (no solvent, solid phase); | 98% |
With sodium hydrogensulfate monohydrate; molybdenum(V) chloride; sodium cyanoborohydride In ethanol for 1.1h; Reflux; | 95% |
With ammonium formate; zinc In methanol for 0.05h; Heating; | 92% |
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With 2-hydroxyethanethiol In N,N-dimethyl-formamide at 20℃; for 1h; | 98% |
Conditions | Yield |
---|---|
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 100℃; for 24h; chemoselective reaction; | 97% |
With ammonium hydroxide; hydrogen In ethanol at 130℃; under 7500.75 Torr; for 12h; Autoclave; | 93.4% |
With ammonia; hydrogen In methanol at 30℃; for 15h; Autoclave; | 92% |
N-(4-methoxybenzyl)-2-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With polystyrene-thiophenol; caesium carbonate; triphenylphosphine In tetrahydrofuran at 20℃; for 24h; | 96% |
With potassium carbonate; thiophenol In acetonitrile at 50℃; | 93% |
With caesium carbonate; thiophenol In N,N-dimethyl-formamide at 20℃; for 0.5h; | 88% |
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 3h; | 96% |
With ammonia at 25℃; Kinetics; Activation energy; Temperature; Reagent/catalyst; | |
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 18 h / Reflux 2: hydrazine hydrate / tetrahydrofuran / 16 h / Reflux View Scheme |
1-(azidomethyl)-4-methoxybenzene
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With hydrogenchloride; indium In tetrahydrofuran at 20℃; for 3h; | 95% |
With 1,3-diphenyl-disiloxane; triphenylphosphine In toluene at 23℃; for 24h; Reagent/catalyst; Solvent; Staudinger Azide Reduction; | 93% |
With cerium(III) chloride; sodium iodide In acetonitrile for 24h; Heating; | 80% |
4-methoxy-selenobenzamide
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With samarium diiodide; water In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 94% |
4-methoxy-benzylamine
Conditions | Yield |
---|---|
Stage #1: N-(2-(4-methoxyphenyl)-2-oxoethyl)picolinamide With hydrogenchloride In water at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With zinc In water at 20℃; for 16h; Inert atmosphere; | 91% |
methyl N-(4'-methoxybenzyl)carbamate
A
methanol
B
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With C25H19BrMnN2O2P; potassium tert-butylate; hydrogen In toluene at 130℃; under 15001.5 Torr; for 48h; | A 87 %Spectr. B 91% |
Conditions | Yield |
---|---|
With ammonia In toluene at 110℃; under 5250.53 Torr; for 30h; | 89% |
With ammonium hydroxide; C19H37IrN4(2+)*2I(1-) at 170℃; for 100h; Sealed tube; | 45% |
Stage #1: 4-Methoxybenzyl alcohol With N-Boc-o-nitrobenzenesulfonamide-aminomethyl polystyrene res; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; Stage #3: With mercaptoethyl alcohol; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; |
N-(4-methoxybenzyl)-2-methylpropane-2-sulfinamide
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; methanol at 25℃; for 0.5h; Inert atmosphere; | 89% |
A
S-(2,4-Dinitrophenyl)-cystein
B
sulfur dioxide
C
4-methoxy-benzylamine
Conditions | Yield |
---|---|
In aq. phosphate buffer for 0.5h; pH=7.4; | A n/a B 84% C n/a |
Conditions | Yield |
---|---|
With titanium tetrachloride; magnesium In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 80% |
With 1,10-Phenanthroline; diethoxymethylane; iron(II) acetate In toluene at 100℃; for 28h; Inert atmosphere; chemoselective reaction; | 60% |
With benzo[b]thiophene-2-boronic acid; phenylsilane In toluene at 130℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 42% |
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate In neat (no solvent) at 25℃; for 0.133333h; Green chemistry; | 80% |
With piperidine In N,N-dimethyl-formamide at 25℃; for 0.166667h; | |
With piperidine In N,N-dimethyl-formamide at 20℃; for 2h; |
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With methanol; sodium hydroxide at 80℃; for 0.166667h; Microwave irradiation; | 80% |
N,N-bis(p-methoxybenzyl)amine
A
4-methoxy-benzaldehyde
B
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; acetic acid In water; acetonitrile for 20h; | A 80% B 8% |
ammonium formate
4-methoxy-benzaldehyde
A
N-(4-methoxybenzyl)formamide
B
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With [pentamethylcyclopentadienyl*Ir(N-phenyl-2-pyridinecarboxamidate)Cl] In methanol at 37℃; for 15h; chemoselective reaction; | A 21 %Spectr. B 79% |
1-hexene
4-Methoxybenzyl alcohol
A
1-(4-methoxyphenyl)-1-heptanone
B
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With 2-Amino-4-methylpyridine; Wilkinson's catalyst; polystyrene-based diphenylphosphine In toluene at 130℃; for 72h; Addition; dehydrogenation; | A 68% B 2% |
4-methoxybenzonitrile
A
N,N-bis(p-methoxybenzyl)amine
B
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel dichloride In ethanol at 20℃; for 0.0833333h; | A 6% B 64% |
With hydrogen In carbon dioxide at 50℃; under 90009 Torr; for 4h; chemoselective reaction; |
methanol
1-(azidomethyl)-4-methoxybenzene
A
N,N-dimethyl-4-methoxylbenzylamine
B
4-methoxy-N-methylbenzylamine
C
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With trans-RuCl(phenpyra-Me)(PPh3)2PF6; sodium hydroxide at 125℃; for 2.5h; Sealed tube; Inert atmosphere; Glovebox; | A 17 %Chromat. B 62% C 6 %Chromat. |
4-methoxybenzylidenediphenylmethylamine
A
Diphenylmethane
B
(diphenylmethyl)[(4-methoxyphenyl)methyl]amine
C
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With sodium In 1,4-dioxane a. 10h, reflux, b. 6h, RT; | A 26% B 39% C 27% |
With sodium In 1,4-dioxane a. 10h, reflux, b. 6h, RT; other educts; | A 26% B 39% C 27% |
1-(azidomethyl)-4-methoxybenzene
A
4-methoxy-benzylamine
B
N-methyl-N-(4-methoxyphenyl)amine
Conditions | Yield |
---|---|
With triethylsilane; tin(IV) chloride In dichloromethane at 0 - 5℃; Rearrangement; Reduction; Addition; | A 13% B 8% C 34% |
N,N'-Bis-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazine
A
(1R,2S)/(1S,2R)-1,2-diamino-1,2-bis(4-methoxyphenyl)ethane
B
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 8h; reduction; | A 13% B 26% C n/a |
With methanesulfonic acid; zinc In tetrahydrofuran at 25℃; for 8h; reduction; | A n/a B 13% C n/a |
p-methoxyl benzaldoxime
A
(1R,2S)/(1S,2R)-1,2-diamino-1,2-bis(4-methoxyphenyl)ethane
B
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With methanesulfonic acid; zinc In acetonitrile at 25℃; reduction; | A n/a B 17% C n/a |
Conditions | Yield |
---|---|
With C5H11NO*CHF3O3S In ethanol; water at 10℃; for 12h; pH=7.4; Inert atmosphere; Sealed tube; Enzymatic reaction; | 17% |
4-methoxyphenylacetamide
A
4-methoxy-benzylamine
B
4-Methoxybenzyl alcohol
Conditions | Yield |
---|---|
With sulfuric acid at 35 - 40℃; bei der elektrolytischen Reduktion; |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
With magnesium sulfate In dichloromethane for 3h; Reflux; | 100% |
In dichloromethane for 18h; Molecular sieve; | 92% |
4-methoxy-benzaldehyde
4-methoxy-benzylamine
N-(4-methoxybenzylidene)-4-methoxybenzylamine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane for 3h; Reflux; | 100% |
In toluene for 24h; Condensation; Heating; | 95% |
(2S)-3-(benzyloxy)-2-methylpropanal
sodium cyanide
4-methoxy-benzylamine
(3R)-2-(4-methoxybenzylamino)-3-benzyloxymethylbutyronitrile
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water for 2h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With oxygen; methylene blue; potassium carbonate In acetonitrile at 20℃; for 10h; Irradiation; Green chemistry; | 100% |
With cobalt nanoparticles encapsulated within nitrogen doped graphitic shells prepared via pyrolysis of poly([1,3-bis(4-vinylbenzyl)imidazolium]CoCl4) at 800 oC In toluene at 120℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
With 2',3',4'-trihydroxyacetophenone In water at 20℃; for 24h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-benzylamine With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 0.166667h; Stage #2: 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0℃; for 0.116667h; | 100% |
Stage #1: 4-methoxy-benzylamine With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 2h; Inert atmosphere; | 98% |
Stage #1: 4-methoxy-benzylamine With hydrogenchloride In dichloromethane; isopropyl alcohol Stage #2: 1,1'-carbonyldiimidazole In dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol at 20℃; for 1.5h; | 87% |
2,3,5-tri-O-benzyl-β-D-arabinofuranoside
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With 4 A molecular sieve In benzene Heating; | 100% |
citraconic acid anhydride
4-methoxy-benzylamine
1-(4-Methoxy-benzyl)-3-methyl-pyrrole-2,5-dione
Conditions | Yield |
---|---|
With acetic acid at 100℃; for 5h; | 100% |
In toluene for 13h; Heating; | 80% |
4-methoxy-benzylamine
Conditions | Yield |
---|---|
In methanol for 5h; Ambient temperature; | 100% |
4-methoxy-benzylamine
2,3-isopropylidene-glyceraldehyde
[1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-(4-methoxy-benzyl)-amine
Conditions | Yield |
---|---|
With magnesium sulfate In diethyl ether at 0℃; for 3h; | 100% |
With magnesium sulfate In diethyl ether at 0℃; Condensation; | |
With magnesium sulfate In dichloromethane for 0.5h; |
2,3,5-tri-O-benzyl-D-arabinofuranose
4-methoxy-benzylamine
((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-(4-methoxy-benzyl)-amine
Conditions | Yield |
---|---|
With 4 A molecular sieve In chloroform; benzene Substitution; Heating; | 100% |
With MS 4 Angstroem In chloroform; benzene Condensation; reflux; | 100% |
4-methoxy-benzylamine
N-[(tert-butoxy)carbonyl]-N-(2-oxo-4-phenylbutyl)glycine
4-[(tert-butoxy)carbonyl]-1-[(4-methoxyphenyl)methyl]-6-(2-phenylethyl)piperazin-2-one
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-benzylamine; N-[(tert-butoxy)carbonyl]-N-(2-oxo-4-phenylbutyl)glycine With sodium tris(acetoxy)borohydride; acetic acid at 25℃; Condensation; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; Cyclization; | 100% |
4-methoxy-benzylamine
acrylonitrile
3-(4-methoxybenzylamino)propanenitrile
Conditions | Yield |
---|---|
With aluminum oxide In neat (no solvent) at 90℃; for 4h; Michael Addition; Green chemistry; | 100% |
aza-Michael reaction; | 84% |
at 20℃; for 45h; | 81% |
4-methoxy-benzylamine
4-Oxo-1-(3-pyridyl)-1-butanone
Conditions | Yield |
---|---|
In methanol; dichloromethane at 20℃; for 1h; | 100% |
4-methoxy-benzylamine
6-(5-benzyloxycarbonylamino-5-methoxycarbonyl-pentylcarbamoyl)-1,3-dihydro-isoindole-2,5-dicarboxylic acid 2-tert-butyl ester
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 16h; | 100% |
4-methoxy-benzylamine
polymer; monomer(s): 2-methyl-3a,4,7,7a-tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione; 2-{4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzyl}-3a,4,7,7a-tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione
polymer; monomer(s): 2-methyl-3a,4,7,7a-tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione; 2-{4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzyl}-3a,4,7,7a-tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione; 4-methoxybenzylamine
Conditions | Yield |
---|---|
With poly(vinylpyridine) In 1,2-dichloro-ethane at 90℃; for 42h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-benzylamine; 1,1'-Thiocarbonyldiimidazole In acetonitrile at 20℃; for 1h; Stage #2: methyl iodide In acetonitrile at 20℃; | 100% |
4-methoxy-benzylamine
[6-benzylsulfonyl-9-(tetrahydropyran-2-yl)-9H-purin-2-yl]-3-methyl-pent-1-yn-3-ol
Conditions | Yield |
---|---|
In tert-butyl alcohol at 20℃; for 0.416667h; | 100% |
bis(trichloromethyl) carbonate
4-methoxy-benzylamine
4-methoxybenzyl isocyanate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -80℃; | |
With sodium hydrogencarbonate In dichloromethane; water at 0℃; for 2.5h; |
4-methoxy-benzylamine
methyl 3-(R)-methyl-5-hydroxypentanoate
(3R)-5-hydroxy-N-(4-methoxybenzyl)-3-methylpentanamide
Conditions | Yield |
---|---|
In toluene at 105 - 110℃; for 4h; | 100% |
In toluene for 3h; Heating; | 97% |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
4-methoxy-benzylamine
benzotriazole-1-carbothioic acid (1,5-dimethylhexyl)amide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 24h; | 100% |
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 100% |
benzaldehyde
4-methoxy-benzylamine
(E)-N-benzylidene-1-(4-methoxyphenyl)methanamine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
With sodium sulfate In dichloromethane at 20℃; for 24h; | 95% |
Stage #1: 4-methoxy-benzylamine In dichloromethane for 0.0833333h; Molecular sieve; Stage #2: benzaldehyde In dichloromethane at 20℃; | 95% |
perfluorobenzaldehyde
4-methoxy-benzylamine
(E)-4-methoxy-N-(pentafluorobenzylidene)benzylamine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere; Darkness; | 100% |
In methanol at 20℃; | 88% |
In benzene Heating; |
2,3,5-tri-O-benzyl-L-xylofuranose
4-methoxy-benzylamine
Conditions | Yield |
---|---|
With 4 A molecular sieve In dichloromethane at 50℃; for 15h; | 100% |
4-methoxy-benzylamine
acrylic acid methyl ester
methyl 3-((4-methoxybenzyl)amino)propanoate
Conditions | Yield |
---|---|
In methanol at 0℃; for 15.5h; | 100% |
With aluminum oxide In neat (no solvent) at 75℃; for 3.5h; Michael Addition; Green chemistry; | 91% |
aza-Michael reaction; | 89% |
With CLEA Pseudomonas stutzeri lipase (PSL) In hexane at 60℃; for 96h; Michael Addition; Sealed tube; Enzymatic reaction; | 74% |
With Pseudomonas fluorescence lipase immobilized on hyroxypropyl methyl cellulose support In toluene at 50℃; for 3h; Reagent/catalyst; Michael Addition; Enzymatic reaction; chemoselective reaction; |
2,2-dimethylsuccinic anhydride
4-methoxy-benzylamine
1-(4-methoxybenzyl)-3,3-dimethylpyrrolidine-2,5-dione
Conditions | Yield |
---|---|
In toluene for 11h; Heating; | 100% |
With dmap; acetic acid Autoclave; Inert atmosphere; | 99% |
Molecular Structure of 4-methoxybenzylamine (CAS NO.2393-23-9):
IUPAC Name: (4-methoxyphenyl)methanamine
Empirical Formula: C8H11NO
Molecular Weight: 137.179
EINECS: 219-247-2
Melting point: -10°C
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 12.47 Å2
Index of Refraction: 1.532
Molar Refractivity: 41.38 cm3
Molar Volume: 133.4 cm3
Surface Tension: 37.3 dyne/cm
Density: 1.028 g/cm3
Flash Point: 98.8 °C
Enthalpy of Vaporization: 47.33 kJ/mol
Boiling Point: 236.5 °C at 760 mmHg
Vapour Pressure: 0.0472 mmHg at 25°C
Sensitive: Air Sensitive
BRN: 508206
InChI
InChI=1/C8H11NO/c1-10-8-4-2-7(6-9)3-5-8/h2-5H,6,9H2,1H3
Smiles
O(c1ccc(cc1)CN)C
Product Categories: Anilines, Aromatic Amines and Nitro Compounds; Amine; Amines; API intermediates; C8; Nitrogen Compounds
Hazard Codes: C
Risk Statements: 34-37-22
R34:Causes burns.
R37:Irritating to respiratory system
R22:Harmful if swallowed.
Safety Statements: 26-36/37/39-45-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S27:Take off immediately all contaminated clothing.
RIDADR: UN 2735 8/PG 2
WGK Germany: 3
Hazard Note: Corrosive
HazardClass: 8
PackingGroup: III
HS Code: 29222900
4-methoxybenzylamine , with CAS number of 2393-23-9, can be called (4-Methoxyphenyl)methanamine ; 1-(4-Methoxyphenyl)methanamine ; 1-Aminomethyl-4-methoxybenzene ; 4-Methoxybenzylamine ; 4-Methoxyphenylmethylamine ; Anisylamine ; p-Methoxybenzylamine . It is a clear colorless to slightly yellow liquid. For the synthesis of pharmaceutical intermediates.
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