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Methoxymethyldiphenylamine is a synthetic organic chemical compound known for its utility in various industrial applications, particularly in the production of black color formers. As a useful research chemical, it plays a significant role in the development and innovation of new materials and products.

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  • 41317-15-1 Structure
  • Basic information

    1. Product Name: Methoxymethyldiphenylamine
    2. Synonyms: ACME;4-METHOXY-2-METHYLDIPHENYLAMINE;methoxymethyldiphenylamine;ANMT/DPA;MMD;4-methoxy-N-phenyl-o-toluidine;2-methyl-4-methoxy diphenylamine C14H15NO;2-methyl-4-methoxy-Diphenylamine(DPA/ANMT)
    3. CAS NO:41317-15-1
    4. Molecular Formula: C14H15NO
    5. Molecular Weight: 213.27
    6. EINECS: 255-310-0
    7. Product Categories: Intermediates of Dyes and Pigments;API intermediates;Heat / pressure-sensitive pigment intermediates
    8. Mol File: 41317-15-1.mol
  • Chemical Properties

    1. Melting Point: 80-83°C
    2. Boiling Point: 171 °C / 4mmHg
    3. Flash Point: 140.1 °C
    4. Appearance: /
    5. Density: 1.089 g/cm3
    6. Vapor Pressure: 6.5E-05mmHg at 25°C
    7. Refractive Index: 1.601
    8. Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
    9. Solubility: almost transparency in Toluene
    10. PKA: 1.35±0.40(Predicted)
    11. Water Solubility: 16.79mg/L at 25℃
    12. CAS DataBase Reference: Methoxymethyldiphenylamine(CAS DataBase Reference)
    13. NIST Chemistry Reference: Methoxymethyldiphenylamine(41317-15-1)
    14. EPA Substance Registry System: Methoxymethyldiphenylamine(41317-15-1)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 22-36
    3. Safety Statements: 26
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 41317-15-1(Hazardous Substances Data)

41317-15-1 Usage

Uses

Used in Chemical Industry:
Methoxymethyldiphenylamine is used as a precursor for the production of black color formers, which are essential in the creation of pigments and dyes for various applications. Its chemical properties make it a valuable component in the synthesis of these colorants, contributing to their stability and performance.
Used in Research and Development:
As a useful research chemical, Methoxymethyldiphenylamine is employed in the exploration of new chemical reactions, synthesis methods, and potential applications. Its unique properties allow researchers to investigate its interactions with other compounds and its potential use in creating novel materials or improving existing ones.

Flammability and Explosibility

Notclassified

Check Digit Verification of cas no

The CAS Registry Mumber 41317-15-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,3,1 and 7 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 41317-15:
(7*4)+(6*1)+(5*3)+(4*1)+(3*7)+(2*1)+(1*5)=81
81 % 10 = 1
So 41317-15-1 is a valid CAS Registry Number.
InChI:InChI=1/C14H15NO/c1-11-10-13(16-2)8-9-14(11)15-12-6-4-3-5-7-12/h3-10,15H,1-2H3

41317-15-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methoxy-2-Methyldiphenylamine

1.2 Other means of identification

Product number -
Other names Methoxymethyldiphenylamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:41317-15-1 SDS

41317-15-1Synthetic route

1-chloro-4-methoxy-2-methylbenzene
13334-71-9

1-chloro-4-methoxy-2-methylbenzene

aniline
62-53-3

aniline

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

4-phenylamino-3-methyl-1-methoxybenzene

Conditions
ConditionsYield
With potassium phosphate; aniline; triphenylphosphine; tris(dibenzylideneacetone)dipalladium (0) at 184℃; for 8h; Buchwald-Hartwig amination;96%
With potassium phosphate; DavePhos; tris-(dibenzylideneacetone)dipalladium(0) at 184℃;96%
methanol
67-56-1

methanol

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

phenol
108-95-2

phenol

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

4-phenylamino-3-methyl-1-methoxybenzene

Conditions
ConditionsYield
Stage #1: methanol; 1-methyl-2-nitrobenzene With 3 % platinum on carbon; hydrogen In water at 50℃; under 750.075 Torr; for 8h; Autoclave; Inert atmosphere;
Stage #2: phenol With 3 % platinum on carbon In cyclohexanone at 250℃; under 7500.75 Torr; for 2h; Autoclave; Inert atmosphere;
95.4%
4-bromo-3-methylanisole
27060-75-9

4-bromo-3-methylanisole

Acetanilid
103-84-4

Acetanilid

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

4-phenylamino-3-methyl-1-methoxybenzene

Conditions
ConditionsYield
Stage #1: Acetanilid With sodium methylate In 1-methyl-pyrrolidin-2-one at 100℃;
Stage #2: 4-bromo-3-methylanisole In 1-methyl-pyrrolidin-2-one at 20 - 40℃; for 1.25h;
Stage #3: In 1-methyl-pyrrolidin-2-one; methanol at 100℃; for 1h; Reagent/catalyst; Temperature; Solvent;
95.3%
4-bromo-3-methylanisole
27060-75-9

4-bromo-3-methylanisole

aniline
62-53-3

aniline

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

4-phenylamino-3-methyl-1-methoxybenzene

Conditions
ConditionsYield
With potassium hydroxide; bis(tri-t-butylphosphine)palladium(0); cetyltrimethylammonim bromide In water; toluene at 90℃; for 0.25h;95%
With caesium carbonate; aniline; DavePhos; tris(dibenzylideneacetone)dipalladium (0) at 184℃; for 8h; Buchwald-Hartwig amination;93%
With caesium carbonate; triphenylphosphine; tris-(dibenzylideneacetone)dipalladium(0) at 184℃;93%
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%
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%
2-(4-methoxy-2-methylphenylamino)benzoic acid

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

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

4-phenylamino-3-methyl-1-methoxybenzene

Conditions
ConditionsYield
With methanol Reagent/catalyst;90.99%
In methanol at 60 - 180℃; for 20h; Sealed tube; Large scale;85.6%
phenylhydrazine
100-63-0

phenylhydrazine

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 cobalt(II) phthalocyanine; copper(l) chloride In dichloromethane at 10℃;86%
bromobenzene
108-86-1

bromobenzene

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

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

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

4-phenylamino-3-methyl-1-methoxybenzene

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

2-methyl-4-methoxyaniline

2-bromobenzoic-acid
88-65-3

2-bromobenzoic-acid

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

4-phenylamino-3-methyl-1-methoxybenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / toluene / 6 h / 100 - 110 °C
2: methanol / 20 h / 60 - 180 °C / Sealed tube; Large scale
View Scheme
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

C14H15NO4S

C14H15NO4S

Conditions
ConditionsYield
With sulfuric acid at 50℃; for 0.5h;98.47%
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

2-(4'-di-n-butylamino-2'-hydroxybenzoyl)benzoic acid
54574-82-2

2-(4'-di-n-butylamino-2'-hydroxybenzoyl)benzoic acid

2'-anilino-3'-methyl-6'-(dibutylamino)spiro[isobenzofuran-1(3H),9'-(9H)xanthen]-3-one
89331-94-2

2'-anilino-3'-methyl-6'-(dibutylamino)spiro[isobenzofuran-1(3H),9'-(9H)xanthen]-3-one

Conditions
ConditionsYield
With sulfuric acid In dichloromethane; water at 35 - 40℃; for 4.5h; Temperature; Solvent;94.6%
Stage #1: 4-phenylamino-3-methyl-1-methoxybenzene; 2-(4'-di-n-butylamino-2'-hydroxybenzoyl)benzoic acid With sulfuric acid at 15 - 25℃; for 24h; Condensation;
Stage #2: With sodium hydroxide In toluene for 1h; Cyclization; Heating;
93%
With sulfuric acid58%
With sulfuric acid58 %Spectr.
With sulfuric acid
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

2-carboxy-4'-(N-ethyl-N-phenyl)amino-2'-hydroxybenzophenone
42529-89-5

2-carboxy-4'-(N-ethyl-N-phenyl)amino-2'-hydroxybenzophenone

3-(N-ethyl-N-phenyl)amino-6-methyl-7-phenylaminofluoran

3-(N-ethyl-N-phenyl)amino-6-methyl-7-phenylaminofluoran

Conditions
ConditionsYield
With sulfuric acid In dichloromethane; water at 35 - 40℃; for 4.5h; Temperature; Solvent;94%
2-carboxy-4'-(N-ethyl-N-isopentyl)amino-2'-hydroxybenzophenone
91458-42-3

2-carboxy-4'-(N-ethyl-N-isopentyl)amino-2'-hydroxybenzophenone

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

4-phenylamino-3-methyl-1-methoxybenzene

2'-anilino-6'-(N-ethyl-N-isopentylamino)-3'-methylspiro[isobenzofuran-1-(3H),9'-(9H)xanthen]-3-one
70516-41-5

2'-anilino-6'-(N-ethyl-N-isopentylamino)-3'-methylspiro[isobenzofuran-1-(3H),9'-(9H)xanthen]-3-one

Conditions
ConditionsYield
With sulfuric acid In dichloromethane; water at 35 - 40℃; for 4.5h; Temperature; Solvent;93.8%
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

2'-Carboxy-4-diethylamino-2-hydroxybenzophenon
5809-23-4

2'-Carboxy-4-diethylamino-2-hydroxybenzophenon

3-(Diethylamino)-6-(methyl)-7-(aminophenyl)xanthen>-3-one

3-(Diethylamino)-6-(methyl)-7-(aminophenyl)xanthen>-3-one

Conditions
ConditionsYield
With sulfuric acid In dichloromethane; water at 35 - 40℃; for 4.5h; Temperature; Solvent;93.8%
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

phenylpropynoic acid methyl ester
4891-38-7

phenylpropynoic acid methyl ester

1-(4-methoxy-2-methyl-phenyl)-2-phenylquinolin-4(1H)-one

1-(4-methoxy-2-methyl-phenyl)-2-phenylquinolin-4(1H)-one

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 120℃; for 12h;90%
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

2-(4'-di-n-butylamino-2'-hydroxybenzoyl)benzoic acid
54574-82-2

2-(4'-di-n-butylamino-2'-hydroxybenzoyl)benzoic acid

3-(dibutylamino)-6-methyl-7-anilinofluoran
197163-54-5

3-(dibutylamino)-6-methyl-7-anilinofluoran

Conditions
ConditionsYield
Stage #1: 2-(4'-di-n-butylamino-2'-hydroxybenzoyl)benzoic acid With sulfuric acid; sulfur trioxide at 15 - 20℃; for 6.75h;
Stage #2: 4-phenylamino-3-methyl-1-methoxybenzene In water; toluene at 20 - 70℃; for 11.25h;
89.6%
4-(4-bromophenyl)bromobenzene
92-86-4

4-(4-bromophenyl)bromobenzene

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

4-phenylamino-3-methyl-1-methoxybenzene

N,N'-bis(2'-methyl-4'-methoxyphenyl)-N,N'-diphenylbenzidine
169685-34-1

N,N'-bis(2'-methyl-4'-methoxyphenyl)-N,N'-diphenylbenzidine

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In toluene at 20 - 130℃; Inert atmosphere;88%
4,4''-diiodo-1,1':4',1''-terphenyl
19053-14-6

4,4''-diiodo-1,1':4',1''-terphenyl

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

4-phenylamino-3-methyl-1-methoxybenzene

N,N'-di(4-methoxy-2-methylphenyl)-N,N'-diphenyl-4,4

N,N'-di(4-methoxy-2-methylphenyl)-N,N'-diphenyl-4,4"-diamino-p-terphenyl

Conditions
ConditionsYield
With potassium carbonate; copper In dodecane at 200 - 210℃; for 30h;80%
1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole
884866-01-7

1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole

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

4-phenylamino-3-methyl-1-methoxybenzene

(Z)-N-(2-((4-methoxy-2-methylphenyl)(phenyl)amino)-2-phenylvinyl)-4-methylbenzenesulfonamide

(Z)-N-(2-((4-methoxy-2-methylphenyl)(phenyl)amino)-2-phenylvinyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 90℃; for 2h; regioselective reaction;80%
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

3-methyl-4-(phenylimino)cyclohexa-2,5-dienone
1257334-76-1

3-methyl-4-(phenylimino)cyclohexa-2,5-dienone

Conditions
ConditionsYield
With sodium cyanide; nitromethane; bis-[(trifluoroacetoxy)iodo]benzene In water at 20℃; for 0.05h;78%
With 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; water In dichloromethane at 15 - 25℃; chemoselective reaction;54%
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

4-methoxy-phenol
150-76-5

4-methoxy-phenol

C21H21NO3

C21H21NO3

Conditions
ConditionsYield
With ammonium peroxydisulfate; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; Irradiation;72%
ferrocenoyl chloride
1293-79-4

ferrocenoyl chloride

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

4-phenylamino-3-methyl-1-methoxybenzene

N-phenyl-N-(2-Methyl-4-Methoxyphenyl)ferrocenecarboxamide

N-phenyl-N-(2-Methyl-4-Methoxyphenyl)ferrocenecarboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 10h; Inert atmosphere;70%
4-Ethoxyphenol
622-62-8

4-Ethoxyphenol

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

4-phenylamino-3-methyl-1-methoxybenzene

C22H23NO3

C22H23NO3

Conditions
ConditionsYield
With ammonium peroxydisulfate; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; Irradiation;70%
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

4-allyloxyphenol
6411-34-3

4-allyloxyphenol

C23H23NO3

C23H23NO3

Conditions
ConditionsYield
With ammonium peroxydisulfate; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; Irradiation;68%
4-Benzyloxyphenol
103-16-2

4-Benzyloxyphenol

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

4-phenylamino-3-methyl-1-methoxybenzene

C27H25NO3

C27H25NO3

Conditions
ConditionsYield
With ammonium peroxydisulfate; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; Irradiation;65%
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

C13H11FO2

C13H11FO2

C27H24FNO3

C27H24FNO3

Conditions
ConditionsYield
With ammonium peroxydisulfate; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; Irradiation;61%
2-bromo-4-methoxyphenol
17332-11-5

2-bromo-4-methoxyphenol

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

4-phenylamino-3-methyl-1-methoxybenzene

C21H20BrNO3

C21H20BrNO3

Conditions
ConditionsYield
With ammonium peroxydisulfate; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; Irradiation;54%
4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

4-(3-bromopropyl)-1,4-hydroquinone
68065-11-2

4-(3-bromopropyl)-1,4-hydroquinone

C23H24BrNO3

C23H24BrNO3

Conditions
ConditionsYield
With ammonium peroxydisulfate; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; Irradiation;52%

41317-15-1Relevant articles and documents

Synthesis of 2-methyl-4-methoxydiphenylamine by palladium catalyzed C-N coupling - High synthetic versatility by use of a flexible catalytic system

Scholz, Ulrich,Schlummer, Bj?rn

, p. 6379 - 6385 (2005)

The synthetic versatility of the Buchwald-Hartwig Amination is demonstrated by the synthesis of the industrially important intermediate 2-methyl-4-methoxydiphenylamine. Using four routes differing in the choice of the starting materials, the diarylamine could be synthesized in excellent yields, however, each reaction required a different combination of ligand, base and solvent. This new approach is compared to established industrial routes.

Preparation method of secondary aromatic amine

-

Paragraph 0024, (2021/03/31)

The invention provides a method for preparing secondary aromatic amine by performing a palladium-catalyzed C-N coupling reaction on (pseudo)aryl halide and (pseudo)heterocyclic aryl halide and primary(heterocyclic)aromatic amine. The method is characterized in that an alkali for promoting the reaction is an alkali metal carboxylate or an alkali metal bicarbonate.

A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines

Shi, Ji-cheng,Zhang, Lixue,Zhou, Fabin

, p. 238 - 243 (2021/09/07)

A terphenyl phosphine ligand (2,6-bis(2,4,6-triisopropylphenyl)phenyl-dicyclohexylphosphine, TXPhos) and its supported palladium complex [(TXPhos)(allyl)PdCl] have been developed and the catalyst system is highly efficient in amination of aryl halides with 1° anilines, especially effective for densely functionalized substrates including both partners possessing ortho-ester, acetyl, nitrile and nitro groups. With the TXPhos-supported catalyst system, many partner combinations have been unprecedentedly realized and the base scope has been even extended to KOAc, which is even the best choice in the amination of 2-nitrochlorobenzene.

Preparation method and application of 2-methyl-4-methoxydiphenylamine

-

Paragraph 0070-0098, (2021/06/23)

The invention relates to the field of preparation of diphenylamine, in particular to a preparation method and application of 2-methyl-4-methoxydiphenylamine, and the preparation method of the 2-methyl-4-methoxydiphenylamine comprises the following steps: (1) in a solvent, reacting 2-methyl-4-methoxyaniline with halogenated benzoic acid in the presence of a catalyst and an acid-binding agent to obtain a condensation product, wherein the acid-binding agent is selected from one or more of carbonate, phosphate and hydroxide of alkali metal; (2) acidifying the condensation product, and conducting filtering, washing and drying to obtain a product 1; and (3) decarboxylating the product 1, and conducting purifying to obtain the product 1. The preparation method of the 2-methyl-4-methoxydiphenylamine is convenient to operate, short in time and suitable for large-scale production, and the production efficiency is greatly improved.

Synthesis method of DPA

-

Paragraph 0007, (2020/01/25)

The invention discloses a synthesis method of DPA. The method comprises the following steps: (1) adding methanol, o-nitrotoluene, a catalyst, concentrated sulfuric acid, distilled water into an autoclave, performing heating with stirring to 50 DEG C, evacuating air and then introducing hydrogen, controlling a pressure in the autoclave to 0.1 MPa, carrying out a reaction for 5 h, then performing suction filtration, distilling a filtrate to remove methanol, diluting a residual solution by adding water and then adjusting pH to be neutral with ammonia water, performing extracting with toluene, washing an organic phase with a dilute sodium hydroxide solution, and performing reduced pressure distillation on the organic phase to obtain 4-methoxy-2-methylaniline; and (2) adding 4-methoxy-2-methylaniline, phenol naphthalene, cyclohexanone, and the catalyst into an autoclave, replacing air with nitrogen, performing heating to 250 DEG C, controlling a pressure in the autoclave to 1 Mpa, performing cooling to room temperature after a reaction is completed, filtering a reaction solution, and performing reduced pressure distillation on a filtrate and collecting various fractions, wherein a latter fraction is DPA. The raw materials are cheap and easy to obtain, the operation is simple, the yield is high, the energy consumption is low, and the method has practical value and economic value, andis suitable for enterprise production.

Synthetic method of -4- 2- methyl-methoxyl diphenylamine (by machine translation)

-

Paragraph 0022-0035, (2019/11/29)

After the reaction is finished, the 2 - organic phase is extracted with DMF toluene, concentrated, vacuum-dried (1) to obtain the intermediate product, (2) and the obtained intermediate product is evaporated and decarboxylated in a methanol system 10~20min 2 - 6~10h 2 . To the synthesis method, the reaction conversion efficiency and selectivity are improved, the raw material conversion rate is improved, the produced process wastewater is less, and the production cost is low. (by machine translation)

Ligand recyclable type method for synthesizing 2-methyl-4-methoxydiphenylamine by catalyzing through copper

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Paragraph 0028; 0108-0109, (2018/07/30)

The invention provides a ligand recyclable type method for synthesizing 2-methyl-4-methoxydiphenylamine by catalyzing through copper. The method takes 2-methyl-4-methoxyaniline and bromobenzene as rawmaterials, an alcohol type compound as a solvent, the copper or a compound of the copper as a catalyst and PSL with a structural formula shown as a formula (I) as a ligand, and the components are subjected to C-N coupling reaction under an alkaline condition at 25 to 120 DEG C, so as to generate the 2-methyl-4-methoxydiphenylamine. The method for synthesizing the 2-methyl-4-methoxydiphenylamine,provided by the invention, has the advantages that reaction conditions are moderate; the green solvent is utilized and is small in environmental pollution; the yield is high, a product is simple to separate and purify and the PSL is easy to recycle; the activity is basically not changed after the ligand is repeatedly used for a plurality of times. The formula (I) is shown in the description.

An Effective Heterogeneous Copper Catalyst System for C-N Coupling and Its Application in the Preparation of 2-Methyl-4-methoxydiphenylamine (MMDPA)

Yi, Zhou,Huang, Manna,Wan, Yiqian,Zhu, Xinhai

, p. 3911 - 3920 (2018/09/29)

A ligand-recyclable, environmentally benign heterogeneous catalyst system composed of CuI and polystyrene-supported N (-(4-(aminomethyl)naphthalen-1-yl)- N (-phenyl-1 H -pyrrole-2-carbohydrazide (PSAP) has been established for Ullmann type C-N coupling based on the homogeneous catalyst system N ′, N ′-diphenyl-1 H -pyrrole-2-carbohydrazide/CuI. This heterogeneous catalyst system maintained the catalytic effectiveness of the homogeneous catalyst. A variety of functionalized aryl bromides can be efficiently aminated with aryl amines and aliphatic amines with high selectivity for amines over alcohols. Moreover, a practical application of this catalyst system to promote the reaction of commercially available 4-methoxy-2-methylaniline and bromobenzene in 10 mmol scale, provided 2-methyl-4-methoxydiphenylamine (MMDPA) with 93% yield with the merit of the approach being simple operation for work-up and purification.

Preparation method of diphenylamine

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Paragraph 0034; 0037; 0040-0042, (2017/10/12)

The invention relates to a preparation method of diphenylamine, and concretely relates to a preparation method of 2-methyl-4-methoxydiphenylamine. The method comprises the following steps: reacting an initial reaction substance 2-methyl-4-methoxyaniline with halogenated benzoic acid to obtain a carboxyl group-containing diphenylamine compound, and carrying out acidification, decarboxylation and purification to obtain the 2-methyl-4-methoxydiphenylamine.

A method for preparing aromatic amine derivative

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Paragraph 0176-0179, (2016/10/08)

The invention discloses a preparation method of a diarylamine ramification. The preparation method comprises the following steps: dissolving a phenylamine ramification, a phenylhydrazine ramification, a metal phthalocyanine ramification and a copper salt into a solvent, and reacting at -10 to 40 DEG C to obtain the diarylamine ramification. According to the preparation method, the phenylamine ramification and the phenylhydrazine ramification are taken as starting materials, so that raw materials are easy to obtain and plenty in variety; a product obtained by utilizing the method is plenty in type, can not only be directly used, but also be used for other further reactions; and no additive is required to be added. The preparation method disclosed by the invention has the advantages of short synthetic route, moderation in reaction condition, simple reaction operation and post-processing process, high yield and suitability for large-scale production.

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