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102-50-1

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102-50-1 Usage

Chemical Properties

brick red crystals or liquid

Uses

4-Methoxy-2-methylaniline is a reagent used in organic synthesis of more complex compounds that have a more specific function. For example, enzyme inhibitors.

General Description

Crystals or brick red liquid.

Air & Water Reactions

Sensitive to prolonged exposure to air and light. Insoluble in water.

Reactivity Profile

2-Methyl-4-methoxybenzenamine neutralizes acids in weakly exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. Reacts with oxidizing agents .

Health Hazard

ACUTE/CHRONIC HAZARDS: 2-Methyl-4-methoxybenzenamine is a local irritant. When heated to decomposition it emits toxic fumes of NOx. 2-Methyl-4-methoxybenzenamine is an experimental animal carcinogen.

Fire Hazard

2-Methyl-4-methoxybenzenamine is probably combustible.

Safety Profile

Suspected carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 102-50-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 2 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 102-50:
(5*1)+(4*0)+(3*2)+(2*5)+(1*0)=21
21 % 10 = 1
So 102-50-1 is a valid CAS Registry Number.

102-50-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (L14910)  4-Methoxy-2-methylaniline, 98%   

  • 102-50-1

  • 5g

  • 611.0CNY

  • Detail
  • Alfa Aesar

  • (L14910)  4-Methoxy-2-methylaniline, 98%   

  • 102-50-1

  • 25g

  • 2069.0CNY

  • Detail
  • Alfa Aesar

  • (L14910)  4-Methoxy-2-methylaniline, 98%   

  • 102-50-1

  • 100g

  • 6437.0CNY

  • Detail

102-50-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methyl-4-methoxybenzenamine

1.2 Other means of identification

Product number -
Other names 4-methoxy-2-methylaniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:102-50-1 SDS

102-50-1Synthetic route

5-methoxy-2-nitrotoluene
5367-32-8

5-methoxy-2-nitrotoluene

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
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
208399-66-0

4-methoxy-2-methylphenyl boronic acid

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;89%
4-bromo-3-methylanisole
27060-75-9

4-bromo-3-methylanisole

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
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
154876-10-5

1-(4-methoxy-2-methylphenyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
With acetic acid; zinc for 0.75h; Ambient temperature;76%
1-chloro-4-methoxy-2-methylbenzene
13334-71-9

1-chloro-4-methoxy-2-methylbenzene

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
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
31601-41-9

N-(4-methoxy-2-methylphenyl)acetamide

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
With hydrogenchloride
methanol
67-56-1

methanol

N-(o-tolyl)hydroxylamine
611-22-3

N-(o-tolyl)hydroxylamine

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
With sulfuric acid at 25℃; durch wochenlange Einw.;
para-methoxynitrobenzene
100-17-4

para-methoxynitrobenzene

methylmagnesium chloride
676-58-4

methylmagnesium chloride

A

N-methyl-N-(4-methoxyphenyl)amine
5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

B

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
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;
4-methoxy-2-methyl-acetophenone oxime

4-methoxy-2-methyl-acetophenone oxime

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
With hydrogenchloride
hydrogenchloride
7647-01-0

hydrogenchloride

1-(4-methoxy-2-methyl-phenyl)-ethanone oxime
75112-71-9

1-(4-methoxy-2-methyl-phenyl)-ethanone oxime

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

1-methoxy-3-methyl-benzene
100-84-5

1-methoxy-3-methyl-benzene

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
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
3-methyl-4-nitrophenol
2581-34-2

3-methyl-4-nitrophenol

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
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
39495-15-3

4-acetamido-3-methylphenol

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: alkali
2: hydrochloric acid
View Scheme
3-methyl-phenol
108-39-4

3-methyl-phenol

KOH

KOH

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HNO3, AcOH
2: (methylation)
3: N2H4*H2O / Raney-Ni
View Scheme
C8H10O2

C8H10O2

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
With glycine ethyl ester hydrochloride; triethylamine In methanol; water at 40℃; Inert atmosphere;
ortho-cresol
95-48-7

ortho-cresol

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
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
1-hydroxy-4-methoxy-2-methylbenzene
5307-05-1

1-hydroxy-4-methoxy-2-methylbenzene

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
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
57197-11-2

4,4-dimethoxy-2-methylcyclohexane-2,5-dien-1-one

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

Conditions
ConditionsYield
With glycine ethyl ester hydrochloride; triethylamine In methanol; water at 40℃; Inert atmosphere;93 %Spectr.
4-chloro-3-nitropyridine
13091-23-1

4-chloro-3-nitropyridine

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

N-(4-methoxy-2-methylphenyl)-3-nitropyridin-4-amine
1513682-06-8

N-(4-methoxy-2-methylphenyl)-3-nitropyridin-4-amine

Conditions
ConditionsYield
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%
2,5-Dimethylpyrrole
625-84-3

2,5-Dimethylpyrrole

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

1-(4-methoxy-2-methyl-phenyl)-2,5-dimethyl-1H-pyrrole

1-(4-methoxy-2-methyl-phenyl)-2,5-dimethyl-1H-pyrrole

Conditions
ConditionsYield
In various solvent(s) at 110℃; pH=3;99%
phenyl chloroformate
1885-14-9

phenyl chloroformate

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

phenyl N-(4-methoxy-2-methylphenyl)carbamate
1378364-99-8

phenyl N-(4-methoxy-2-methylphenyl)carbamate

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0 - 20℃;99%
With pyridine In tetrahydrofuran at 0 - 20℃;81.1%
BOC-glycine
4530-20-5

BOC-glycine

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

[(4-methoxy-2-methylphenylcarbamoyl)methyl]carbamic acid tert-butyl ester
1448525-54-9

[(4-methoxy-2-methylphenylcarbamoyl)methyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
108-24-7

acetic anhydride

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

N-(4-methoxy-2-methylphenyl)acetamide
31601-41-9

N-(4-methoxy-2-methylphenyl)acetamide

Conditions
ConditionsYield
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
87-13-8

diethyl 2-ethoxymethylenemalonate

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

diethyl 2-((4-methoxy-2-methylphenylamino)methylene)malonate
384820-97-7

diethyl 2-((4-methoxy-2-methylphenylamino)methylene)malonate

Conditions
ConditionsYield
at 120℃; for 1h;98%
In toluene for 5h; Reflux;14.4 g
2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

(2-methyl-4-methoxyphenyl)diazonium tetrafluoroborate

(2-methyl-4-methoxyphenyl)diazonium tetrafluoroborate

Conditions
ConditionsYield
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-bromo-4-methyl-1-(3-methylbut-1-enyl)benzene

2-bromo-4-methyl-1-(3-methylbut-1-enyl)benzene

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

4-methoxy-2-methyl-N-(5-methyl-2-(3-methylbut-1-enyl)phenyl)aniline

4-methoxy-2-methyl-N-(5-methyl-2-(3-methylbut-1-enyl)phenyl)aniline

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); sodium tert-pentoxide; XPhos In 1,4-dioxane at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere;98%
pivaloyl chloride
3282-30-2

pivaloyl chloride

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

4'-methoxy-2'-methylpivalanilide

4'-methoxy-2'-methylpivalanilide

Conditions
ConditionsYield
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
7338-94-5

1,3-diphenyl-2-propynone

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

(Z)-3-(4-methoxy-2-methylphenylamino)-1,3-diphenylprop-2-en-1-one
1198463-75-0

(Z)-3-(4-methoxy-2-methylphenylamino)-1,3-diphenylprop-2-en-1-one

Conditions
ConditionsYield
In methanol at 80℃; for 1h; Sealed tube;96%
In ethanol Michael Addition; Reflux;96%
1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

N-TMS-4-Methoxy-2-methylaniline
109463-66-3

N-TMS-4-Methoxy-2-methylaniline

Conditions
ConditionsYield
With cyclohexane-1,2-epoxide; lithium iodide; chloro-trimethyl-silane In neat (no solvent) for 1h; Heating;95%
(E)-N'-(2-cyano-4,5-dimethoxyphenyl)-N,N-dimethylformimidamide

(E)-N'-(2-cyano-4,5-dimethoxyphenyl)-N,N-dimethylformimidamide

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

(6,7-dimethoxyquinazolin-4-yl)-(4-methoxy-2-methylphenyl)amine

(6,7-dimethoxyquinazolin-4-yl)-(4-methoxy-2-methylphenyl)amine

Conditions
ConditionsYield
With acetic acid In acetonitrile at 160℃; for 0.166667h; microwave irradiation;95%
2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

(E)-N'-(2-cyano-4-nitrophenyl)-N,N'-dimethylformimidamide

(E)-N'-(2-cyano-4-nitrophenyl)-N,N'-dimethylformimidamide

(4-methoxy-2-methylphenyl)-(6-nitroquinazolin-4-yl)amine

(4-methoxy-2-methylphenyl)-(6-nitroquinazolin-4-yl)amine

Conditions
ConditionsYield
With acetic acid In acetonitrile at 160℃; for 0.166667h; microwave irradiation;95%
chlorobenzene
108-90-7

chlorobenzene

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

Conditions
ConditionsYield
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
108-86-1

bromobenzene

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

Conditions
ConditionsYield
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
796048-82-3

5-(4-benzyloxy-benzenesulfonyl)-4-chloro-2-methyl-pyrimidine

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

[5-(4-Benzyloxybenzenesulfonyl)-2-methylpyrimidin-4-yl]-(4-methoxy-2-methylphenyl)-amine

[5-(4-Benzyloxybenzenesulfonyl)-2-methylpyrimidin-4-yl]-(4-methoxy-2-methylphenyl)-amine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 1h; Heating / reflux;95%
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

4-methoxy-2-methyl-N-(2-tolyl)aniline
100925-29-9

4-methoxy-2-methyl-N-(2-tolyl)aniline

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium t-butanolate In toluene at 100℃; for 4h;95%
2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

A

4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
A n/a
B 94%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

N-(4-methoxy-2-methylphenyl)-3-oxobutanamide

N-(4-methoxy-2-methylphenyl)-3-oxobutanamide

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 80℃; for 12h; Sealed tube; Green chemistry;94%
2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

N'-(2-cyano-4-methylphenyl)-N,N-dimethylformamidine

N'-(2-cyano-4-methylphenyl)-N,N-dimethylformamidine

(4-methoxy-2-methylphenyl)-(6-methylquinazolin-4-yl)amine

(4-methoxy-2-methylphenyl)-(6-methylquinazolin-4-yl)amine

Conditions
ConditionsYield
With acetic acid In acetonitrile at 160℃; for 0.166667h; microwave irradiation;93%
2,2,2-trifluroethylamine hydrochloride
373-88-6

2,2,2-trifluroethylamine hydrochloride

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

4-methoxy-2-methyl-N-(2,2,2-trifluoroethyl)aniline

4-methoxy-2-methyl-N-(2,2,2-trifluoroethyl)aniline

Conditions
ConditionsYield
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%
1,3-dimethoxy-2-hydroxy-benzene
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

C16H17NO4

C16H17NO4

Conditions
ConditionsYield
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
102-50-1

2-methyl-4-methoxyaniline

N'-(2-cyano-3-methylphenyl)-N,N-dimethylformamidine

N'-(2-cyano-3-methylphenyl)-N,N-dimethylformamidine

(4-methoxy-2-methylphenyl)-(5-methylquinazolin-4-yl)amine

(4-methoxy-2-methylphenyl)-(5-methylquinazolin-4-yl)amine

Conditions
ConditionsYield
With acetic acid In acetonitrile at 160℃; for 0.166667h; microwave irradiation;92%
trifluoroacetic acid
76-05-1

trifluoroacetic acid

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

(Z)-2,2,2-trifluoro-N-(4-methoxy-2-methylphenyl)acetimidoyl chloride

(Z)-2,2,2-trifluoro-N-(4-methoxy-2-methylphenyl)acetimidoyl chloride

Conditions
ConditionsYield
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
4635-59-0

4-Chlorobutanoyl chloride

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

1-[2-methyl-4-(methyloxy)phenyl]-2-pyrrolidinone
727993-66-0

1-[2-methyl-4-(methyloxy)phenyl]-2-pyrrolidinone

Conditions
ConditionsYield
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
16714-25-3

2-azidobenzaldehyde

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

2-(4-methoxy-2-methylphenyl)-2H-indazole
1393125-78-4

2-(4-methoxy-2-methylphenyl)-2H-indazole

Conditions
ConditionsYield
at 100℃; under 10343.2 Torr; Microwave irradiation;92%
2,3-diethynylquinoxaline
91-19-0

2,3-diethynylquinoxaline

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

2-(4-methoxy-2-methylphenyl)quinoxaline

2-(4-methoxy-2-methylphenyl)quinoxaline

Conditions
ConditionsYield
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%
allyl acetoacetate
1118-84-9

allyl acetoacetate

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

N-(4-methoxy-2-methylphenyl)-3-oxobutanamide

N-(4-methoxy-2-methylphenyl)-3-oxobutanamide

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 80℃; for 12h; Sealed tube; Green chemistry;92%
sodium carbonate
497-19-8

sodium carbonate

chlorobenzene
108-90-7

chlorobenzene

2-methyl-4-methoxyaniline
102-50-1

2-methyl-4-methoxyaniline

2-(4-methoxy-2-methylphenylamino)benzoic acid

2-(4-methoxy-2-methylphenylamino)benzoic acid

Conditions
ConditionsYield
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%

102-50-1Relevant articles and documents

Palladium on Polydopamine: Its True Potential in Catalytic Transfer Hydrogenations and Heck Coupling Reactions

Kunfi, Attila,Szabó, Vivien,Mastalir, ágnes,Bucsi, Imre,Mohai, Miklós,Németh, Péter,Bertóti, Imre,London, Gábor

, p. 3236 - 3244 (2017)

The application of Pd–polydopamine and magnetic Fe3O4@Pd–polydopamine catalysts in catalytic transfer hydrogenation reactions and the Heck arylation is reported. The reduction of a wide range of aromatic nitro-compounds bearing both electron-donating and -withdrawing substituents to the corresponding anilines could be efficiently performed, although the reduction of carbonyl compounds was found to be less general. In the latter case, only aromatic ketones could be reduced to the corresponding alcohols, whereas aldehyde substrates were unaffected, which may be owing to their reaction with the catalyst support leading to catalyst deactivation. By using magnetic Fe3O4@Pd–polydopamine system, facilitated catalyst recovery and reuse for five consecutive cycles without considerable loss of activity in nitro-group reduction. The efficiency of the catalyst in Heck reactions was comparable to that in transfer hydrogenation, however, no catalytic activity was observed upon reuse in this case, likely as a result of metal leaching. We also explored tandem Heck reaction/catalytic transfer hydrogenation sequences, however, the two reactions showed limited compatibility under the applied conditions.

Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid

Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Pi, Danwei,Shen, Guanshuo

, p. 3898 - 3904 (2017)

An unprecedented palladium-catalyzed chemoselective reduction and reductive amination of nitroarenes with water as a hydrogen source mediated by diboronic acid have been discovered. A series of aryl amines containing various reducible functional groups were obtained in good to excellent yields.

Methoxy aniline compound and synthesis method thereof

-

Paragraph 0027; 0030-0032; 0041-0042, (2021/05/19)

The invention mainly relates to a preparation method of anisidine. According to the technical scheme, under the promotion of the photocatalyst and blue light, in the argon atmosphere, nitro compounds and methanol generate methoxyaniline, wherein products and additional products with stable molecular structures and excellent chemical properties are prepared, wherein a photocatalyst and a blue light source are used in the method, and a new path is provided for synthesis of methoxyaniline compounds. The method has the characteristics of mild reaction conditions, simple reaction system, less reaction equipment, simplicity and convenience in experimental operation and the like. The methoxyaniline derivative and the synthetic method thereof can be applied to a plurality of industrial production fields of dyes, pesticides, medicines, rubber additives and the like. The method is particularly suitable for scientific research, development and utilization of efficient and selective synthesis of methoxyaniline compounds by a one-pot method.

Synthesis method of aminobenzoate compound (by machine translation)

-

Paragraph 0094-0098; 0137-0139, (2020/08/09)

The synthesis method comprises the following steps: carrying out a hydrogenation reduction reaction of a nitroanisole compound with a carbon-coated nickel containing alkaline earth metal in a hydrogen atmosphere; wherein the shell layer is a graphitized carbon layer containing alkaline earth metal, nitrogen and oxygen. To the method, the alkaline earth metal-containing carbon-coated nano composite material is used as a catalyst, the carbon material and the nickel nanoparticles cooperate to play a good catalytic effect, and the alkaline earth metal of the shell layer further synergistically improves the catalytic performance of the material. (by machine translation)

Synthesis method of amino-anisole compound

-

Paragraph 0057; 0154-0156, (2020/08/09)

The invention provides a synthesis method of an amino-anisole compound. The synthesis method comprises the following steps: taking a carbon-coated nickel nano composite material containing alkali metals as a catalyst, and catalyzing a hydrogenation reduction reaction of a nitro-anisole compound in a hydrogen atmosphere; wherein the nano composite material contains a core-shell structure with a shell layer and an inner core, the shell layer is a graphitized carbon layer containing alkali metals and oxygen, and the inner core is nickel nano particles. According to the method, the nano compositematerial is used as a catalyst; a carbon material and the nickel nano particles generate a synergistic effect and a good catalytic effect, the alkali metals of the shell layer further synergisticallyimprove the catalytic performance of the nano composite material, and the catalyst is used for hydrogenation reduction of nitro-anisole compounds to synthesize amino-anisole compounds, and has excellent activity, selectivity and safety.

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