Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide In isopropyl alcohol under 2327.2 Torr; | 98.5% |
With sodium formate In ethanol at 85℃; for 1h; | 87% |
With tetrahydroxydiboron; water at 80℃; for 8h; | 80% |
4-methoxy-2-methylphenyl boronic acid
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h; | 89% |
4-bromo-3-methylanisole
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With ammonium sulfate; (R)-(-)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(tri-ortho-tolylphosphine)palladium(0); sodium t-butanolate In 1,4-dioxane at 100℃; for 6h; Inert atmosphere; Glovebox; | 80% |
With ammonium hydroxide; copper(l) iodide; potassium carbonate; 4R-4-hydroxyproline In dimethyl sulfoxide at 70℃; for 36h; | 77% |
1-(4-methoxy-2-methylphenyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With acetic acid; zinc for 0.75h; Ambient temperature; | 76% |
1-chloro-4-methoxy-2-methylbenzene
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(2,4,6-trimethoxyphenyl)oxalamide In water; dimethyl sulfoxide at 120℃; for 48h; Inert atmosphere; | 64% |
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; ammonia; sodium t-butanolate In 1,4-dioxane at 65℃; for 24h; Inert atmosphere; chemoselective reaction; | 52% |
N-(4-methoxy-2-methylphenyl)acetamide
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With sulfuric acid at 25℃; durch wochenlange Einw.; |
para-methoxynitrobenzene
methylmagnesium chloride
A
N-methyl-N-(4-methoxyphenyl)amine
B
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; palladium on activated charcoal 1) THF, 20 min, -30 deg C, 2) 20 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; |
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With hydrogenchloride |
hydrogenchloride
1-(4-methoxy-2-methyl-phenyl)-ethanone oxime
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / ZnCl2 / diethyl ether; CH2Cl2 / 0.5 h / 25 °C 2: 76 percent / Zn, glacial acetic acid / 0.75 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; xylene 2: tin (II)-chloride; hydrochloric acid View Scheme | |
Multi-step reaction with 2 steps 1: alkaline solution 2: tin; hydrochloric acid; alcohol View Scheme | |
Multi-step reaction with 2 steps 1: diethyl ether 2: tin; hydrochloric acid View Scheme | |
Multi-step reaction with 2 steps 1: (methylation) 2: N2H4*H2O / Raney-Ni View Scheme |
4-acetamido-3-methylphenol
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: alkali 2: hydrochloric acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: HNO3, AcOH 2: (methylation) 3: N2H4*H2O / Raney-Ni View Scheme |
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With glycine ethyl ester hydrochloride; triethylamine In methanol; water at 40℃; Inert atmosphere; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: [bis(acetoxy)iodo]benzene / 0 - 20 °C / Inert atmosphere 2: triethylamine; glycine ethyl ester hydrochloride / methanol; water / 40 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: [bis(acetoxy)iodo]benzene / 0.53 h / 0 - 20 °C / Inert atmosphere 1.2: 1 h / 0 - 20 °C / Inert atmosphere 2.1: [bis(acetoxy)iodo]benzene / 0 - 20 °C / Inert atmosphere 3.1: triethylamine; glycine ethyl ester hydrochloride / methanol; water / 40 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: [bis(acetoxy)iodo]benzene / 0 - 20 °C / Inert atmosphere 2: triethylamine; glycine ethyl ester hydrochloride / methanol; water / 40 °C / Inert atmosphere View Scheme |
4,4-dimethoxy-2-methylcyclohexane-2,5-dien-1-one
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With glycine ethyl ester hydrochloride; triethylamine In methanol; water at 40℃; Inert atmosphere; | 93 %Spectr. |
4-chloro-3-nitropyridine
2-methyl-4-methoxyaniline
N-(4-methoxy-2-methylphenyl)-3-nitropyridin-4-amine
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; for 16h; | 100% |
With triethylamine In ethanol at 20℃; for 16h; | 100% |
With triethylamine In ethanol at 20℃; for 16h; | 100% |
Conditions | Yield |
---|---|
In various solvent(s) at 110℃; pH=3; | 99% |
phenyl chloroformate
2-methyl-4-methoxyaniline
phenyl N-(4-methoxy-2-methylphenyl)carbamate
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 0 - 20℃; | 99% |
With pyridine In tetrahydrofuran at 0 - 20℃; | 81.1% |
BOC-glycine
2-methyl-4-methoxyaniline
[(4-methoxy-2-methylphenylcarbamoyl)methyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere; | 99% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 5h; |
acetic anhydride
2-methyl-4-methoxyaniline
N-(4-methoxy-2-methylphenyl)acetamide
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; Inert atmosphere; | 98% |
In dichloromethane at 25℃; for 3h; Large scale; | 91.8% |
In dichloromethane at 20℃; | 82% |
diethyl 2-ethoxymethylenemalonate
2-methyl-4-methoxyaniline
diethyl 2-((4-methoxy-2-methylphenylamino)methylene)malonate
Conditions | Yield |
---|---|
at 120℃; for 1h; | 98% |
In toluene for 5h; Reflux; | 14.4 g |
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
Stage #1: 2-methyl-4-methoxyaniline With tetrafluoroboric acid at 0℃; Stage #2: With sodium nitrite at 0 - 20℃; for 3h; Further stages.; | 98% |
With tetrafluoroboric acid; sodium nitrite at 0℃; | 96% |
Stage #1: 2-methyl-4-methoxyaniline With boron trifluoride diethyl etherate In tetrahydrofuran for 0.0833333h; Cooling with ice; Stage #2: With tert.-butylnitrite In tetrahydrofuran at 0℃; | 90% |
Stage #1: 2-methyl-4-methoxyaniline With tetrafluoroboric acid In water at 20℃; Stage #2: With sodium nitrite In water at 10℃; Cooling with ice; | 78% |
Stage #1: 2-methyl-4-methoxyaniline With tetrafluoroboric acid In water at 20℃; for 0.166667h; Stage #2: With sodium nitrite In water at 0 - 20℃; for 1h; |
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); sodium tert-pentoxide; XPhos In 1,4-dioxane at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0℃; for 0.5h; | 97% |
With sodium carbonate In dichloromethane; water at 80℃; for 2h; | 93% |
With triethylamine In ethyl acetate |
1,3-diphenyl-2-propynone
2-methyl-4-methoxyaniline
(Z)-3-(4-methoxy-2-methylphenylamino)-1,3-diphenylprop-2-en-1-one
Conditions | Yield |
---|---|
In methanol at 80℃; for 1h; Sealed tube; | 96% |
In ethanol Michael Addition; Reflux; | 96% |
1,1,1,3,3,3-hexamethyl-disilazane
2-methyl-4-methoxyaniline
N-TMS-4-Methoxy-2-methylaniline
Conditions | Yield |
---|---|
With cyclohexane-1,2-epoxide; lithium iodide; chloro-trimethyl-silane In neat (no solvent) for 1h; Heating; | 95% |
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With acetic acid In acetonitrile at 160℃; for 0.166667h; microwave irradiation; | 95% |
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With acetic acid In acetonitrile at 160℃; for 0.166667h; microwave irradiation; | 95% |
chlorobenzene
2-methyl-4-methoxyaniline
4-phenylamino-3-methyl-1-methoxybenzene
Conditions | Yield |
---|---|
With potassium phosphate; DavePhos; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃; for 8h; Buchwald-Hartwig amination; | 95% |
With potassium phosphate; DavePhos; tris-(dibenzylideneacetone)dipalladium(0) In toluene Heating; | 95% |
bromobenzene
2-methyl-4-methoxyaniline
4-phenylamino-3-methyl-1-methoxybenzene
Conditions | Yield |
---|---|
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃; Buchwald-Hartwig amination; | 95% |
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) In toluene Heating; | 95% |
With potassium phosphate; copper(l) iodide; C18H15N3O2 at 25℃; for 24h; Reagent/catalyst; Temperature; Sealed tube; | 93% |
With potassium phosphate; copper(l) iodide In diethylene glycol at 70℃; for 14h; Sealed tube; | 93% |
5-(4-benzyloxy-benzenesulfonyl)-4-chloro-2-methyl-pyrimidine
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 1h; Heating / reflux; | 95% |
2-methylphenyl bromide
2-methyl-4-methoxyaniline
4-methoxy-2-methyl-N-(2-tolyl)aniline
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium t-butanolate In toluene at 100℃; for 4h; | 95% |
2-methyl-4-methoxyaniline
A
4-phenylamino-3-methyl-1-methoxybenzene
B
phenol
Conditions | Yield |
---|---|
A n/a B 94% |
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 80℃; for 12h; Sealed tube; Green chemistry; | 94% |
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With acetic acid In acetonitrile at 160℃; for 0.166667h; microwave irradiation; | 93% |
Conditions | Yield |
---|---|
Stage #1: 2,2,2-trifluroethylamine hydrochloride With acetic acid; sodium nitrite In dichloromethane; water at 20℃; for 0.5h; Stage #2: 2-methyl-4-methoxyaniline With C50H23Cl8FeN4O10 In dichloromethane; water for 12.5h; | 93% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; meso-tetraphenylporphyrin iron(III) chloride; 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; regioselective reaction; | 93% |
2-methyl-4-methoxyaniline
Conditions | Yield |
---|---|
With acetic acid In acetonitrile at 160℃; for 0.166667h; microwave irradiation; | 92% |
Conditions | Yield |
---|---|
With tetrachloromethane; triethylamine; triphenylphosphine for 3h; Heating; | 92% |
With triethylamine; triphenylphosphine In tetrachloromethane for 3h; Heating; | 92% |
Stage #1: trifluoroacetic acid With tetrachloromethane; triethylamine; triphenylphosphine at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-methyl-4-methoxyaniline at 0 - 85℃; Inert atmosphere; | 89% |
4-Chlorobutanoyl chloride
2-methyl-4-methoxyaniline
1-[2-methyl-4-(methyloxy)phenyl]-2-pyrrolidinone
Conditions | Yield |
---|---|
Stage #1: 4-Chlorobutanoyl chloride; 2-methyl-4-methoxyaniline With triethylamine In tetrahydrofuran at 0 - 10℃; for 1.5h; Stage #2: With potassium tert-butylate In tetrahydrofuran at 0 - 10℃; for 2h; | 92% |
2-azidobenzaldehyde
2-methyl-4-methoxyaniline
2-(4-methoxy-2-methylphenyl)-2H-indazole
Conditions | Yield |
---|---|
at 100℃; under 10343.2 Torr; Microwave irradiation; | 92% |
Conditions | Yield |
---|---|
Stage #1: 2-methyl-4-methoxyaniline With tetrafluoroboric acid; tert.-butylnitrite In ethanol; water at 0 - 20℃; Stage #2: 2,3-diethynylquinoxaline With tetrabutylammonium tetrafluoroborate; trifluoroacetic acid In acetonitrile at 20℃; for 4.5h; Electrochemical reaction; | 92% |
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 80℃; for 12h; Sealed tube; Green chemistry; | 92% |
Conditions | Yield |
---|---|
Stage #1: sodium carbonate; chlorobenzene With copper In N,N-dimethyl-formamide; toluene for 0.25h; Reflux; Stage #2: 2-methyl-4-methoxyaniline In N,N-dimethyl-formamide; toluene under 760.051 Torr; for 10.6h; Reagent/catalyst; Solvent; Reflux; | 91.47% |
1. | otr-rat:emb 51,500 ng/plate | JJATDK JAT, Journal of Applied Toxicology. 1 (1981),190. |
Suspected carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Other safty informations about 2-METHYL-p-ANISIDINE(102-50-1):
Hazard Codes: Xi,Xn,T (Irritant;Harmful;Toxic)
Risk Statements :
R36/37/38:Irritating to eyes, respiratory system and skin
R40:Limited evidence of a carcinogenic effect
R45 :May cause cancer
Safety Statements :
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
S53:Avoid exposure - obtain special instruction before use
S45 :In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR : 2810
WGK Germany : 3
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