Conditions | Yield |
---|---|
Stage #1: p-toluidine With n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: phenylmagnesium bromide With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane In tetrahydrofuran; hexane at 0 - 20℃; for 3h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; | 100% |
Conditions | Yield |
---|---|
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate; ruphos In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; | 99% |
With sodium t-butanolate; catacxium A In toluene at 110℃; for 12h; Buchwald-Hartwig reaction; | 99% |
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 20℃; for 18h; | 99% |
With [Pd(N,N'-bis(2,6-bis(di-p-tolylmethyl)-4-methylphenyl)-imidazol-2-ylidene)(acetylacetonate)Cl]; lithium hexamethyldisilazane In 1,4-dioxane at 110℃; for 3h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube; | 99% |
With nickel(II) bromide trihydrate; N,N-dimethyl-cyclohexanamine; C70H75BN2 In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 16h; Mechanism; Product distribution; other amines; other aryl halides and tosylates; var. chelating alkylphosphines, var. time, var. temp., further solvent; | 99% |
With (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 16h; | 99% |
With potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 5h; | 99% |
Conditions | Yield |
---|---|
With nickel(II) iodide; potassium phosphate; 2-Phenyl-1,3,2-dioxaborinane In 1,4-dioxane at 115℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere; chemoselective reaction; | 99% |
With C29H25CuIN3OPPd; sodium t-butanolate In toluene at 40℃; for 24h; | 94% |
With nickel(II) chloride hexahydrate; triethylamine at 125℃; for 0.333333h; Microwave irradiation; Neat (no solvent); | 92% |
Conditions | Yield |
---|---|
With sodium t-butanolate; palladium diacetate; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine In 1,2-dimethoxyethane at 100℃; for 24h; | 99% |
With bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 1.5h; Inert atmosphere; | 99% |
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate; ruphos In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With C59H74F4OPPd(1+)*CF3O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene In tert-butyl methyl ether at 20℃; for 0.333333h; Catalytic behavior; Reagent/catalyst; | 99% |
With caesium carbonate; palladium diacetate In toluene at 100℃; for 8h; | |
With palladium diacetate; caesium carbonate; XPhos In toluene at 100℃; for 1.5h; |
Conditions | Yield |
---|---|
With SingaCycle-A3; potassium hexamethylsilazane In 1,4-dioxane; toluene at 100℃; for 12h; Schlenk technique; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
copper In dichloromethane for 11h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
copper In dichloromethane for 0.75h; Ambient temperature; | 97% |
Conditions | Yield |
---|---|
With SingaCycle-A1; sodium t-butanolate In tetrahydrofuran at 60℃; for 1h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; regioselective reaction; | 97% |
Conditions | Yield |
---|---|
With potassium fluoride In dimethyl sulfoxide at 130℃; for 2h; Ullmann-Goldberg Substitution; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With copper acetylacetonate; potassium hydroxide In glycerol at 100℃; for 15h; Inert atmosphere; Green chemistry; | 96% |
With triethylamine In N,N-dimethyl-formamide at 80℃; for 2h; Ullmann Condensation; | 96% |
With triethylamine In N,N-dimethyl-formamide at 80℃; for 2h; Ullmann Condensation; | 96% |
Conditions | Yield |
---|---|
With Fe3O4 magnetic nanoparticles-supported EDTA-copper(II) complex In water at 50℃; for 1h; Green chemistry; | 96% |
With polystyrene-supported Cu(I) catalyst In methanol at 40℃; for 15h; Ullmann coupling; Inert atmosphere; | 94% |
With (1,3-bis(2,6-diisopropyl-4-((E)-3-methoxy-3-oxoprop-1-en-1-yl)phenyl)-2,3-dihydro-1H-imidazole-2-yl)copper(I) chloride In dichloromethane at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Chan-Lam Coupling; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 20℃; for 8h; | 96% |
With C21H16CuN2O2; potassium carbonate In water at 28℃; for 12h; Chan-Lam Coupling; | 95% |
With Fe3O4 magnetic nanoparticles-supported EDTA-copper(II) complex In water at 50℃; for 2h; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With potassium hydroxide; copper(II) oxide In dimethyl sulfoxide at 110℃; for 1.6h; | 96% |
Conditions | Yield |
---|---|
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 5.5h; Inert atmosphere; | 96% |
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 5.5h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate at 120℃; for 4.8h; | 96% |
Conditions | Yield |
---|---|
With [(2,6-bis(2,4,6-triisopropylphenyl)phenyl)dicyclohexylphosphine](allyl-η3)palladium(II) chloride; potassium hydrogencarbonate In tert-butyl alcohol at 100℃; for 12h; Inert atmosphere; Sealed tube; | 96% |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate In toluene at 20 - 105℃; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With styrene; 10 wt% Pd(OH)2 on carbon In toluene at 140℃; under 3750.38 Torr; for 11.5h; Flow reactor; | 95% |
With 1,10-Phenanthroline; oxygen; palladium diacetate In toluene at 135℃; for 37h; Sealed tube; | 82% |
With styrene; Au-Pd/Al2O3 In 1,3,5-trimethyl-benzene at 130℃; under 760.051 Torr; for 24h; Schlenk technique; Inert atmosphere; | 73% |
With gold-palladium bimetallic nanoparticles supported on TiO2 In 1,3,5-trimethyl-benzene at 160℃; under 760.051 Torr; for 24h; Inert atmosphere; Schlenk technique; | 85 %Chromat. |
Conditions | Yield |
---|---|
With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; potassium phosphate; palladium diacetate; phenylboronic acid In butan-1-ol at 110℃; for 15h; Inert atmosphere; | 94% |
With potassium phosphate; C36H50Cl3N5Pd In tert-Amyl alcohol at 120℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; chemoselective reaction; | 87% |
With (1,3-bis(2,6-diisopropylphenyl)imidazolidene)Ni(styrene)2; lithium tert-butoxide In 1,4-dioxane for 3h; Inert atmosphere; Heating; Schlenk technique; | 80% |
Conditions | Yield |
---|---|
Stage #1: p-toluidine With n-butyllithium In hexane; chlorobenzene at 0 - 20℃; for 0.5h; Stage #2: With zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) In hexane; chlorobenzene for 1h; Stage #3: diphenylzinc With iron(III)-acetylacetonate; 1,2-dichloro-2-methylpropane In hexane; chlorobenzene at 80℃; for 15h; | 94% |
p-toluidine
phenylmagnesium bromide
A
biphenyl
B
4-methyldiphenylamine
Conditions | Yield |
---|---|
Stage #1: p-toluidine With n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: phenylmagnesium bromide With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane In tetrahydrofuran; hexane at 0 - 20℃; for 3h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; | A 17 %Chromat. B 94% |
Conditions | Yield |
---|---|
With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium; copper(I) bromide In acetonitrile at 60℃; for 16h; Ullmann Condensation; Inert atmosphere; Glovebox; Sealed tube; | 94% |
Conditions | Yield |
---|---|
With pyridine; copper diacetate trihydrate In dichloromethane at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Chan-Lam Coupling; | 93% |
1,1'-sulfinylbisbenzene
p-toluidine
methyl iodide
A
racemic methyl phenyl sulfoxide
B
N,4-dimethyl-N-phenylaniline
C
4-methyldiphenylamine
Conditions | Yield |
---|---|
Stage #1: 1,1'-sulfinylbisbenzene; p-toluidine With potassium tert-butylate In 1,4-dioxane at 60℃; Inert atmosphere; Stage #2: methyl iodide In 1,4-dioxane at 25℃; for 1.5h; Inert atmosphere; regioselective reaction; | A 93% B n/a C n/a |
Conditions | Yield |
---|---|
With copper diacetate; triethylamine at 20℃; for 24h; | 92% |
With triethylamine at 20℃; for 15h; | 90% |
With triethylamine at 90℃; for 17h; Stille Cross Coupling; | 81% |
With triethylamine at 95℃; | 76% |
Conditions | Yield |
---|---|
With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; potassium phosphate; palladium diacetate; phenylboronic acid In butan-1-ol at 110℃; for 15h; Inert atmosphere; | 91% |
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; bis(tri-ortho-tolylphosphine)palladium(0); sodium t-butanolate In toluene at 25℃; for 24h; Inert atmosphere; | 87% |
With 1,1'-bis-(diphenylphosphino)ferrocene; [1,1′-bis(diphenylphosphino)ferrocene]bis(triphenylphosphite)nickel(0); sodium t-butanolate In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere; | 47% |
With sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; chlorobis(triphenylphosphine)(1-naphthyl)nickel(II) In 1,4-dioxane at 110℃; for 0.5h; | 46% |
Conditions | Yield |
---|---|
With iodine; sulfur In 1,2-dichloro-benzene at 160℃; for 0.75h; Inert atmosphere; | 14% |
With iodine; sulfur | |
With iodine; sulfur at 195℃; | |
With iodine; sulfur at 280℃; | |
With iodine; sulfur In water at 190℃; for 0.333333h; microwave irradiation; |
Conditions | Yield |
---|---|
With sulfur; iodine In 1,2-dichloro-benzene at 160℃; for 2h; Heating / reflux; | 28% |
Conditions | Yield |
---|---|
With dibenzoyl peroxide In chloroform for 6h; Heating; Irradiation; | 40% |
With oxygen In acetic acid; toluene at 80℃; under 760.051 Torr; | |
With oxygen; palladium diacetate; acetic acid In toluene at 100℃; for 6.5h; | |
With oxygen; acetic acid In toluene Inert atmosphere; |
4-methyldiphenylamine
Conditions | Yield |
---|---|
With copper; potassium carbonate In nitrobenzene Substitution; Ullmann reaction; Heating; | 40.9% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; | 41% |
Conditions | Yield |
---|---|
With pyridine; oxygen; copper dichloride In 2-methyl-propan-1-ol at 100℃; for 16h; Schlenk technique; Green chemistry; regioselective reaction; | 45% |
Conditions | Yield |
---|---|
With oxygen; copper(l) chloride In 2-methyl-propan-1-ol at 100℃; for 12h; chemoselective reaction; | 46% |
Conditions | Yield |
---|---|
With oxygen; copper dichloride In 1,4-dioxane at 80℃; for 16h; Molecular sieve; chemoselective reaction; | 46% |
Conditions | Yield |
---|---|
With potassium carbonate; copper; copper(l) chloride In pyridine at 210 - 220℃; for 10h; | 47% |
Conditions | Yield |
---|---|
With iodine In N,N-dimethyl-formamide at 90℃; for 16h; | 48% |
4-methyldiphenylamine
Conditions | Yield |
---|---|
With copper; potassium carbonate In nitrobenzene Substitution; Ullmann reaction; Heating; | 49.7% |
4-methyldiphenylamine
4-bromo-4'-iodobiphenyl
N,N'-di(4''-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In 1,2-dichloro-benzene at 200℃; for 70h; Inert atmosphere; | 50% |
Conditions | Yield |
---|---|
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 95℃; for 4h; | 51% |
4-methyldiphenylamine
Conditions | Yield |
---|---|
With oxygen; copper diacetate In 1,2-dichloro-ethane at 130℃; for 24h; Sealed tube; | 53% |
IUPAC Name: 4-Methyl-N-phenylaniline
Molecular Formula: C13H13N
Molar mass: 183.249 g/mol
EINECS: 210-655-6
Density: 1.066 g/cm3
Melting point: 90 °C
Flash Point: 154.9 °C
Index of Refraction: 1.621
Surface Tension: 42.3 dyne/cm
Boiling Point: 334 °C at 760 mmHg
Vapour Pressure: 0.000132 mmHg at 25 °C
Structure of 4-Methyldiphenylamine(620-84-8):
Product Categories: electronic; pharmacetical; Amines; Electronic Chemicals; Diphenylamines (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research
Canonical SMILES: CC1=CC=C(C=C1)NC2=CC=CC=C2
InChI: InChI=1S/C13H13N/c1-11-7-9-13(10-8-11)14-12-5-3-2-4-6-12/h2-10,14H,1H3
InChIKey: AGHYMXKKEXDUTA-UHFFFAOYSA-N
4-Methyldiphenylamine(620-84-8) is organic synthesis's intermediates and can be used as reagent for high-performance polymer research.
4-Methyldiphenylamine , its cas register number is 620-84-8. It also can be called N-Phenyl-p-toluidine; 4-Methyl-N-phenylbenzenamine .
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View