Conditions | Yield |
---|---|
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 80℃; for 12h; | 99% |
With bis(η3-allyl-μ-chloropalladium(II)); 2,6-bis(2,4,6-triisopropylphenyl)phenyl(dicyclohexylphosphine); sodium t-butanolate In dodecane; toluene at 100℃; for 6h; Catalytic behavior; Reagent/catalyst; Glovebox; | 99% |
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 70℃; for 16h; | 97% |
Conditions | Yield |
---|---|
With potassium hydroxide; bis(tri-tert-butylphosphine)palladium(0); cetyltrimethylammonim bromide In water; toluene at 90℃; for 6h; | 99% |
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry; | 99% |
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In toluene at 50℃; | 97% |
Conditions | Yield |
---|---|
With copper(l) iodide; 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; sodium t-butanolate In toluene at 110℃; for 40h; post-Ullmann reaction; | 96% |
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium hydroxide In dimethyl sulfoxide at 120℃; for 3h; | 96% |
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In toluene at 30℃; | 93% |
Conditions | Yield |
---|---|
With dichloro{1,10-[di-(2-diizopropylaminoethyl)]-3,3'-o-xylyldibenzimidazolidin-2,2'-diylidene}palladium (II); potassium tert-butylate In 1,2-dimethoxyethane at 80℃; for 15h; Buchwald-Hartwig amination; Inert atmosphere; | 95% |
With (6-Dipp)PdCl2-SPhos; sodium t-butanolate In neat (no solvent) at 110℃; for 24h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; | 90% |
With potassium hydroxide In water for 24h; Buchwald-Hartwig reaction; Reflux; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; potassium tert-butylate; copper(l) iodide In toluene at 115℃; for 3.5h; | 94% |
With tetraethoxy orthosilicate; caesium carbonate; copper(l) iodide at 145℃; for 38h; Ullmann coupling reaction; | 85% |
With C39H33CuF3N2P2(1+)*ClO4(1-); potassium tert-butylate In toluene at 90℃; for 12h; Inert atmosphere; | 80% |
1-bromo-4-methoxy-benzene
N-(trimethylsilyl)-diphenylamine
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 1h; Inert atmosphere; | 94% |
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 1h; Time; Reagent/catalyst; Inert atmosphere; | 94% |
With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene hydrochloride; potassium tert-butylate; cesium fluoride at 100℃; for 36h; Inert atmosphere; | 67% |
4-methoxy-aniline
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 20℃; for 72h; | 90% |
bromobenzene
4-methoxy-aniline
A
N-(4-methoxyphenyl)phenylamine
B
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
With C46H58Br2N4O10Pd; potassium tert-butylate In 1,2-dimethoxyethane at 80℃; for 15h; Inert atmosphere; Buchwald-Hartwig amination; | A 11% B 89% |
With potassium tert-butylate; copper(l) iodide; tributylphosphine In toluene at 135℃; for 10.5h; high pressure; | A 2% B 86% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux; | A 41% B 45% |
4-methoxy-aniline
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
A
N-(4-methoxyphenyl)phenylamine
B
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 20℃; for 10h; | A 89% B 4% |
4-methoxy-aniline
chlorobenzene
A
N-(4-methoxyphenyl)phenylamine
B
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
With potassium tert-butylate; copper(l) iodide; tributylphosphine In toluene at 135℃; for 10.5h; high pressure; | A 3% B 85% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; (E)-2-(((2,5-bis(trifluoromethyl)phenyl)imino)methyl)phenol; sodium t-butanolate In o-xylene at 145℃; for 12h; Schlenk technique; Inert atmosphere; | 85% |
iodobenzene
4-methoxy-aniline
A
N-(4-methoxyphenyl)phenylamine
B
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
With potassium tert-butylate; copper(l) iodide In toluene at 135℃; for 14h; | A 12% B 82% |
With copper(l) iodide; cesium fluoride In dimethyl sulfoxide at 130℃; for 24h; Ullmann Condensation; Inert atmosphere; Glovebox; | A 37 %Chromat. B 15% |
Conditions | Yield |
---|---|
potassium hydroxide; copper In various solvent(s) at 160℃; for 5h; | 79% |
bromobenzene
N-(4-methoxyphenyl)phenylamine
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
Stage #1: bromobenzene With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: N-(4-methoxyphenyl)phenylamine With sodium t-butanolate In toluene at 90℃; for 20h; Hartwig-Buchwald coupling; | 79% |
With C37H50BrO3PPd In 1,4-dioxane at 80℃; Kinetics; Inert atmosphere; Glovebox; Sealed tube; |
N-(4-methoxyphenyl)phenylamine
triphenylbismuth(V) diacetate
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
copper In dichloromethane for 72h; Ambient temperature; | 78% |
triphenylbismuth(V) diacetate
4-methoxy-aniline
A
N-(4-methoxyphenyl)phenylamine
B
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
copper In dichloromethane for 24h; Ambient temperature; | A 28% B 68% |
Conditions | Yield |
---|---|
With potassium phosphate; bis(acetylacetonato)palladium(II); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In n-heptane at 130℃; for 24h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere; | 66% |
With potassium phosphate; bis(acetylacetonato)palladium(II); BrettPhos In n-heptane at 130℃; for 24h; | 66% |
With bis(acetylacetonato)palladium(II); tripotassium phosphate "n" hydrate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In n-heptane at 130℃; for 24h; Inert atmosphere; | 61% |
4-Methoxyphenyl isocyanate
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 100℃; for 14h; Inert atmosphere; | 46% |
Diphenyliodonium triflate
4-methoxy-aniline
A
N-(4-methoxyphenyl)phenylamine
B
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
Stage #1: Diphenyliodonium triflate; 4-methoxy-aniline With copper(l) iodide; 2,6-di-tert-butyl-pyridine In toluene at 20℃; for 12h; Schlenk technique; Inert atmosphere; Stage #2: With copper(l) iodide; 1,10-Phenanthroline; potassium tert-butylate In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere; | A 5% B 44% |
1.4-dibromobenzene
4-methoxy-aniline
A
N-(4-methoxyphenyl)phenylamine
B
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 110℃; Hartwig-Buchwald coupling; Inert atmosphere; | A 42% B 9% |
4-methoxy-aniline
A
N-(4-methoxyphenyl)phenylamine
B
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
Product distribution; effect of amount of Ph3Bi(OAc)2 and reaction time; |
1-bromo-4-methoxy-benzene
diphenylamine
A
N,N-diphenyl-4-methoxyaniline
B
N-(3-methoxyphenyl)-diphenylamine
Conditions | Yield |
---|---|
With potassium hydroxide; PEGDM-400 In toluene at 158 - 161℃; for 8h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With iron(III) oxide; potassium tert-butylate In dimethyl sulfoxide at 130℃; for 36h; regioselective reaction; |
iodobenzene
para-iodoanisole
diphenylamine
A
N,N-diphenylaminobenzene
B
N,N-diphenyl-4-methoxyaniline
Conditions | Yield |
---|---|
potassium hydroxide; copper at 160℃; Rate constant; Mechanism; competitive reaction, var. catalysts; |
Conditions | Yield |
---|---|
With copper at 195℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94 percent / KOH; Pd[P(t-Bu3)]2; cetyltrimethylammonium bromide / toluene; H2O / 3 h / 90 °C 2: 99 percent / KOH; Pd[P(t-Bu3)]2; cetyltrimethylammonium bromide / toluene; H2O / 6 h / 90 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94 percent / KOH; Pd[P(t-Bu3)]2; cetyltrimethylammonium bromide / toluene; H2O / 3 h / 90 °C 2: 99 percent / KOH; Pd[P(t-Bu3)]2; cetyltrimethylammonium bromide / toluene; H2O / 6 h / 90 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 1 h / Ambient temperature 2: 97 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 16 h / 70 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 1 h / Ambient temperature 2: 97 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 16 h / 70 °C View Scheme | |
Multi-step reaction with 2 steps 1: 75 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 25 h / Ambient temperature 2: 97 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 16 h / 70 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 25 h / Ambient temperature 2: 97 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 16 h / 70 °C View Scheme |
N,N-diphenyl-4-methoxyaniline
4-hydroxyltriphenylamine
Conditions | Yield |
---|---|
Stage #1: N,N-diphenyl-4-methoxyaniline With boron tribromide In dichloromethane; chloroform at 0 - 20℃; for 6h; Inert atmosphere; Stage #2: With methanol In dichloromethane; chloroform Inert atmosphere; Cooling with ice; | 100% |
Stage #1: N,N-diphenyl-4-methoxyaniline With boron tribromide In dichloromethane at 0 - 20℃; for 24.5h; Stage #2: With water In dichloromethane | 99% |
With boron tribromide In dichloromethane at 20℃; for 3h; | 90% |
N,N-diphenyl-4-methoxyaniline
4,4′-dibromo-4′′-methoxytriphenylamine
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 3h; | 95% |
With N-Bromosuccinimide |
N,N-diphenyl-4-methoxyaniline
N,N-dimethyl-formamide
4-[N-phenyl-N-(4-methoxyphenyl)amino]benzaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate In 1,2-dichloro-ethane for 4h; Vilsmeier formylation; Inert atmosphere; Reflux; | 94% |
With trichlorophosphate at 0 - 80℃; for 1h; Inert atmosphere; | 94.8% |
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.75h; Vilsmeier-Haack Formylation; Stage #2: N,N-diphenyl-4-methoxyaniline at 60℃; for 2h; Vilsmeier-Haack Formylation; | 85% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In toluene at 100℃; for 6h; Sealed tube; Glovebox; Inert atmosphere; | 87% |
N,N-diphenyl-4-methoxyaniline
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With C26H45OSiY In hexane at 100℃; for 24h; regioselective reaction; | 83% |
N,N-diphenyl-4-methoxyaniline
4,4-diiodo-4''-methoxytriphenylamine
Conditions | Yield |
---|---|
With potassium iodate; potassium iodide In water; acetic acid at 80℃; for 3h; Iodination; | 82% |
With potassium iodate; potassium iodide In acetic acid | |
With potassium iodate; potassium iodide In acetic acid |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); C23H28N4 In tetrahydrofuran; m-xylene at 60℃; for 4h; Kumada Cross-Coupling; Inert atmosphere; Sealed tube; | 81% |
Conditions | Yield |
---|---|
With zinc(II) chloride In dichloromethane | 80% |
N,N-diphenyl-4-methoxyaniline
4,4’-bisformyl-4’’-methoxytriphenylamine
Conditions | Yield |
---|---|
76.5% |
N,N-diphenyl-4-methoxyaniline
N,N-dimethyl-formamide
4,4’-bisformyl-4’’-methoxytriphenylamine
Conditions | Yield |
---|---|
With trichlorophosphate In 1,2-dichloro-ethane at 0℃; for 15h; Vilsmeier-Haack Formylation; Inert atmosphere; Reflux; | 75% |
With trichlorophosphate at 95℃; for 4h; Inert atmosphere; | 71% |
With trichlorophosphate In 1,2-dichloro-benzene at 85℃; for 24h; Vilsmeyer reaction; | 67% |
With trichlorophosphate In 1,2-dichloro-ethane for 6h; Reflux; | 36.7% |
With trichlorophosphate at 80℃; for 24h; Vilsmeier-Haack Formylation; |
1-Methylbenzimidazole
N,N-diphenyl-4-methoxyaniline
4-(1-methyl-1H-benzimidazol-2-yl)-N,N-diphenylbenzenamine
Conditions | Yield |
---|---|
With ortho-tolylmagnesium bromide; bis(1,5-cyclooctadiene)nickel (0); C23H30N4 In m-xylene at 90℃; for 16h; | 75% |
N,N-diphenyl-4-methoxyaniline
4-(N-phenyl-N-(4-methoxy)phenylamino)-1-bromobenzene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 5h; | 75% |
N,N-diphenyl-4-methoxyaniline
N4,N4'-bis(4-methoxyphenyl)-N4,N4'-diphenyl-4,4'-diaminobiphenyl
Conditions | Yield |
---|---|
Stage #1: N,N-diphenyl-4-methoxyaniline With methanesulfonic acid In dichloromethane at 0℃; Stage #2: With chloranil In dichloromethane at 0 - 20℃; for 3h; | 66% |
With tetrafluoroboric acid diethyl ether; C22H42N12*2BF4(1-)*2H(1+) In acetonitrile at 20℃; Reagent/catalyst; Cooling with ice; | 90 %Spectr. |
Molecule structure of 4-Methoxytriphenylamine 97 (CAS NO.4316-51-2):
Molecular Weight: 275.3444 g/mol
Molecular Formula: C19H17NO
Density: 1.126 g/cm3
Melting Point: 102-106 °C(lit.)
Boiling Point: 415.435 °C at 760 mmHg
Flash Point: 121.934 °C
Index of Refraction: 1.628
Molar Refractivity: 86.775 cm3
Molar Volume: 244.596 cm3
Surface Tension: 45.39 dyne/cm
Enthalpy of Vaporization: 66.852 kJ/mol
InChI: InChI=1/C19H17NO/c1-21-19-14-12-18(13-15-19)20(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-15H,1H3 InChIKey of 4-Methoxytriphenylamine 97 (CAS NO.4316-51-2): KIGTXAWIOISJOG-UHFFFAOYAO
Hazard Codes: Xi
Risk Statements: 36/37/38-43
R36/37/38:Irritating to eyes, respiratory system and skin.
R43:May cause sensitization by skin contact.
Safety Statements: 26-36/37/39
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.
WGK Germany: 3
4-Methoxytriphenylamine 97 (CAS NO.4316-51-2) is also named as 4-methoxy-n,n-diphenylaniline ; Diphenyl(4-methoxyphenyl)amine ; Diphenyl(p-methoxyphenyl)amine ; N,N-Diphenyl-4-methoxyaniline ; N,N-Diphenyl-p-anisidine ; p-Anisyldiphenylamine .
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