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10541-83-0 Usage

Description

4-(Methylamino) benzoic acid is an important intermediate for production of pharmaceutical products, dyes, flavors and preservatives.

Chemical Properties

white to beige powder

Uses

4-(Methylamino)benzoic acid important for the preparation of other pharmaceutical products, dyes, flavors, and preservatives. .For the preparation of medicines and other fine chemicals.

References

https://www.alfa.com/en/catalog/A12426/

Check Digit Verification of cas no

The CAS Registry Mumber 10541-83-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,5,4 and 1 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 10541-83:
(7*1)+(6*0)+(5*5)+(4*4)+(3*1)+(2*8)+(1*3)=70
70 % 10 = 0
So 10541-83-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO2/c1-9-7-4-2-6(3-5-7)8(10)11/h2-5,9H,1H3,(H,10,11)/p-1

10541-83-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A12426)  4-(Methylamino)benzoic acid, 97%   

  • 10541-83-0

  • 5g

  • 293.0CNY

  • Detail
  • Alfa Aesar

  • (A12426)  4-(Methylamino)benzoic acid, 97%   

  • 10541-83-0

  • 25g

  • 1121.0CNY

  • Detail
  • Alfa Aesar

  • (A12426)  4-(Methylamino)benzoic acid, 97%   

  • 10541-83-0

  • 100g

  • 3989.0CNY

  • Detail
  • Aldrich

  • (119695)  4-(Methylamino)benzoicacid  97%

  • 10541-83-0

  • 119695-10G

  • 704.34CNY

  • Detail
  • Aldrich

  • (119695)  4-(Methylamino)benzoicacid  97%

  • 10541-83-0

  • 119695-50G

  • 2,602.08CNY

  • Detail

10541-83-0SDS

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 4-(Methylamino)benzoic acid

1.2 Other means of identification

Product number -
Other names N-Methyl-4-aminobenzoate

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:10541-83-0 SDS

10541-83-0Synthetic route

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
Stage #1: p-N,N-dimethylaminobenzoic acid With 1,4-diaza-bicyclo[2.2.2]octane; rose bengal; acetic acid In acetonitrile at 20℃; for 2h; Flow reactor; Irradiation;
Stage #2: With sulfuric acid In methanol; water at 20℃; for 12h;
96%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

methylamine
74-89-5

methylamine

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With copper In water at 100℃; for 12h; Ullmann reaction;93.3%
4-(benzotriazol-1-ylmethyl-amino)-benzoic acid
62001-43-8

4-(benzotriazol-1-ylmethyl-amino)-benzoic acid

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran for 0.333333h; Heating;91%
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

methyl 4-(N-methyl)aminobenzoate
18358-63-9

methyl 4-(N-methyl)aminobenzoate

C

4-methoxycarbonyl aniline
619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran for 2h; Methylation; esterification; Heating;A 10 % Spectr.
B 5 % Spectr.
C 76%
Ethyl N-acetyl-N-methyl-4-aminobenzoate

Ethyl N-acetyl-N-methyl-4-aminobenzoate

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride; water Heating / reflux;74%
With hydrogenchloride at 90 - 92℃; for 4.5h;64.2%
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With sodium-exchanged Y-zeolite at 130℃; for 9h;A 74%
B n/a
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
NaY-faujasite at 130℃; for 9h;74%
methylamine
74-89-5

methylamine

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With copper In water at 100℃; for 48h; Ullmann reaction;56.4%
4-bromo-N-methylaniline
6911-87-1

4-bromo-N-methylaniline

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With n-butyllithium; diethyl ether anschliessend Behandeln mit Kohlendioxid;
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With aqueous alkali
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

methyl iodide
74-88-4

methyl iodide

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With methanol; potassium hydroxide
With potassium hydroxide
With methanol; potassium hydroxide
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; formaldehyd; zinc
N-methylaniline
100-61-8

N-methylaniline

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With magnesium; methyl iodide at 190 - 200℃; im Kohlendioxydstrom und Zersetzung der Magnesiumverbindung mit Salmiak;
Dimethyl-p-toluidine
99-97-8

Dimethyl-p-toluidine

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
in der tierischen Organismus;
C9H11N2O4S(1-)

C9H11N2O4S(1-)

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With water at 25℃; Rate constant; Mechanism;
4-[N-methyl-N-(trifluoroacetyl)amino]benzoic acid
50734-07-1

4-[N-methyl-N-(trifluoroacetyl)amino]benzoic acid

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Conditions
ConditionsYield
With 1-benzyl-1-aza-18-crown-6; barium thiocyanate; tetramethyl-ammonium; ethylate In ethanol at 25℃; Rate constant; other aza<18>crown-6 compound; also without Ba(SCN)2; inhibition with 4-MeCON(Me)C6H4COOH or 4-MeNHC6H4COOH;
methanol
67-56-1

methanol

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

methyl iodide
74-88-4

methyl iodide

alkaline solution

alkaline solution

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

diluted NaOH-solution

diluted NaOH-solution

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

diluted NaOH-solution

diluted NaOH-solution

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

diethyl ether
60-29-7

diethyl ether

carbon dioxide
124-38-9

carbon dioxide

N-methylaniline
100-61-8

N-methylaniline

methyl iodide
74-88-4

methyl iodide

Mg

Mg

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

C

N-methylated anthranilic acid

N-methylated anthranilic acid

hydrogenchloride
7647-01-0

hydrogenchloride

methyl N-methyl-N-nitroso-4-aminobenzoate
18600-49-2

methyl N-methyl-N-nitroso-4-aminobenzoate

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

hydrogenchloride
7647-01-0

hydrogenchloride

ethyl 4-N-methyl-N-nitrosoaminobenzoate
208176-48-1

ethyl 4-N-methyl-N-nitrosoaminobenzoate

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

sulfuric acid
7664-93-9

sulfuric acid

4-(acetyl-methyl-amino)-isophthalic acid
871886-64-5

4-(acetyl-methyl-amino)-isophthalic acid

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

2-(2-Methoxyethoxy)ethyl methyl carbonate
141814-27-9

2-(2-Methoxyethoxy)ethyl methyl carbonate

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With NaY faujasite In diethylene glycol dimethyl ether at 135℃; for 10h; Kinetics;
ethyl p-acetamidobenzoate
5338-44-3

ethyl p-acetamidobenzoate

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

N-methylated anthranilic acid

N-methylated anthranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / 60percent aq. NaOH, benzyltriethylammonium chloride / benzene / 5 h / 40 °C
2: 64.2 percent / aq. HCl / 4.5 h / 90 - 92 °C
View Scheme
O2-{2,4-dinitro-5-((4-N-methylamino)benzoyloxy-phenyl)}-1-(N,N-dimethylamino)-diazen-1-ium 1,2-diolate
875769-11-2

O2-{2,4-dinitro-5-((4-N-methylamino)benzoyloxy-phenyl)}-1-(N,N-dimethylamino)-diazen-1-ium 1,2-diolate

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

C8H9N5O7

C8H9N5O7

Conditions
ConditionsYield
With water In aq. phosphate buffer; dimethyl sulfoxide at 25℃; pH=7.4; Kinetics; Temperature;
GLUTATHIONE
70-18-8

GLUTATHIONE

O2-{2,4-dinitro-5-((4-N-methylamino)benzoyloxy-phenyl)}-1-(N,N-dimethylamino)-diazen-1-ium 1,2-diolate
875769-11-2

O2-{2,4-dinitro-5-((4-N-methylamino)benzoyloxy-phenyl)}-1-(N,N-dimethylamino)-diazen-1-ium 1,2-diolate

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

C8H9N5O7

C8H9N5O7

C

C24H26N6O12S

C24H26N6O12S

D

C18H24N8O12S

C18H24N8O12S

E

C26H34N8O16S2

C26H34N8O16S2

F

C16H19N5O11S

C16H19N5O11S

G

C18H24N4O7S

C18H24N4O7S

Conditions
ConditionsYield
In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 0.5h; pH=7.4; Kinetics;
GLUTATHIONE
70-18-8

GLUTATHIONE

O2-{2,4-dinitro-5-((4-N-methylamino)benzoyloxy-phenyl)}-1-(N,N-dimethylamino)-diazen-1-ium 1,2-diolate
875769-11-2

O2-{2,4-dinitro-5-((4-N-methylamino)benzoyloxy-phenyl)}-1-(N,N-dimethylamino)-diazen-1-ium 1,2-diolate

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

C8H9N5O7

C8H9N5O7

C

C24H26N6O12S

C24H26N6O12S

D

C26H34N8O16S2

C26H34N8O16S2

E

C16H19N5O11S

C16H19N5O11S

F

C18H24N4O7S

C18H24N4O7S

Conditions
ConditionsYield
With glutathione S-transferase P1 In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 0.0166667h; pH=7.4; Enzymatic reaction;
methanol
67-56-1

methanol

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

methyl 4-(N-methyl)aminobenzoate
18358-63-9

methyl 4-(N-methyl)aminobenzoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 72h; Heating;100%
With toluene-4-sulfonic acid for 18h; Reflux;100%
With toluene-4-sulfonic acid for 18h; Reflux;100%
2-amino-4-(morpholin-4-yl)-6-(1-bromomethyl)-1,3,5-triazine
871332-14-8

2-amino-4-(morpholin-4-yl)-6-(1-bromomethyl)-1,3,5-triazine

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4-({[2-amino-4-(morpholin-4-yl)-1,3,5-triazin-6-yl]methyl}methylamino)benzoic acid

4-({[2-amino-4-(morpholin-4-yl)-1,3,5-triazin-6-yl]methyl}methylamino)benzoic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 12h;99%
2-amino-4-(4-phenylpiperazin-1-yl)-6-(1-bromomethyl)-1,3,5-triazine
871332-12-6

2-amino-4-(4-phenylpiperazin-1-yl)-6-(1-bromomethyl)-1,3,5-triazine

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4-({[2-amino-4-(4-phenylpiperazin-1-yl)-1,3,5-triazin-6-yl]methyl}methylamino)benzoic acid
871332-19-3

4-({[2-amino-4-(4-phenylpiperazin-1-yl)-1,3,5-triazin-6-yl]methyl}methylamino)benzoic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 12h;97%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4-(formyl-methyl-amino)-benzoic acid
51865-84-0

4-(formyl-methyl-amino)-benzoic acid

Conditions
ConditionsYield
In formic acid; water97%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

N-(4-(1H-benzoimidazol-2-yl)-phenyl)-N-methyl-amine
105383-61-7

N-(4-(1H-benzoimidazol-2-yl)-phenyl)-N-methyl-amine

Conditions
ConditionsYield
With polyphosphoric acid at 210℃; for 4h;96%
Stage #1: N-methyl-p-aminobenzoic acid; 1,2-diamino-benzene at 200 - 210℃; for 4h;
Stage #2: With water at 20 - 80℃;
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

Propargylamine
2450-71-7

Propargylamine

4-(methylamino)-N-(prop-2-yn-1-yl)benzamide

4-(methylamino)-N-(prop-2-yn-1-yl)benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;95.6%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

3-chloro-4-(methylamino)benzoic acid
72228-73-0

3-chloro-4-(methylamino)benzoic acid

Conditions
ConditionsYield
With tert-butylhypochlorite In acetic acid94.5%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

3-Bromo-4-ethylbenzoic acid
99548-53-5

3-Bromo-4-ethylbenzoic acid

Conditions
ConditionsYield
Stage #1: N-methyl-p-aminobenzoic acid With pyridine In dichloromethane at 20℃; for 1h;
Stage #2: With bromine In dichloromethane at -20℃; for 5h; Reagent/catalyst; Solvent;
94%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

terephthaloyl chloride
100-20-9

terephthaloyl chloride

C24H20N2O6

C24H20N2O6

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 25℃; Inert atmosphere;93%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

2-((2,4-difluorobenzyl)(pyridin-2-yl)amino)ethanol
1352211-82-5

2-((2,4-difluorobenzyl)(pyridin-2-yl)amino)ethanol

2-[(2,4-difluorobenzyl)(pyridin-2-yl)amino]ethyl 4-(methylamino)benzoate

2-[(2,4-difluorobenzyl)(pyridin-2-yl)amino]ethyl 4-(methylamino)benzoate

Conditions
ConditionsYield
Stage #1: N-methyl-p-aminobenzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.05h;
Stage #2: 2-((2,4-difluorobenzyl)(pyridin-2-yl)amino)ethanol In dichloromethane at 25℃;
92%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

tetramethylammonium trifluoromethanethiolate

tetramethylammonium trifluoromethanethiolate

4-((fluorocarbonothioyl)(methyl)amino)benzoyl fluoride

4-((fluorocarbonothioyl)(methyl)amino)benzoyl fluoride

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;92%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

4-<<(benzyloxy)carbonyl>methylamino>benzoic acid
2528-30-5

4-<<(benzyloxy)carbonyl>methylamino>benzoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran at 0 - 25℃; for 18h;91.13%
With sodium hydroxide In 1,4-dioxane; water at 0 - 5℃; for 0.5h;86%
With sodium hydrogencarbonate In tetrahydrofuran at 0 - 21℃; for 2h;78%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4,5-dimethoxyanthranilamide
5004-88-6

4,5-dimethoxyanthranilamide

4,5-Dimethoxy-2-(4-methylamino-benzoylamino)-benzamide
334025-80-8

4,5-Dimethoxy-2-(4-methylamino-benzoylamino)-benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 50h;91%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride
73978-41-3

2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid
19741-14-1

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid

Conditions
ConditionsYield
Stage #1: 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride In water at 20 - 80℃; for 0.0833333h;
Stage #2: With dibromotriphenylphosphorane In N,N-dimethyl acetamide at 20℃; for 20h;
Stage #3: N-methyl-p-aminobenzoic acid With N-ethyl-N,N-diisopropylamine at 20℃; for 72h;
90%
Stage #1: 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride With dibromotriphenylphosphorane In N,N-dimethyl acetamide at 20℃; for 24h; Inert atmosphere;
Stage #2: N-methyl-p-aminobenzoic acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20 - 60℃; for 72h;
56%
Stage #1: 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride With bromine; triphenylphosphine In ISOPROPYLAMIDE at 0 - 20℃; for 20h;
Stage #2: N-methyl-p-aminobenzoic acid With N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 60 - 70℃; for 24h;
Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

N-methyl-1,2-phenylenediamine
4760-34-3

N-methyl-1,2-phenylenediamine

N-(4-(1-methyl-1H-benzoimidazol-2-yl)-phenyl)-N-methyl-amine
105383-62-8

N-(4-(1-methyl-1H-benzoimidazol-2-yl)-phenyl)-N-methyl-amine

Conditions
ConditionsYield
With polyphosphoric acid at 200℃; for 3h;90%
Stage #1: N-methyl-p-aminobenzoic acid; N-methyl-1,2-phenylenediamine at 200 - 210℃; for 4h;
Stage #2: With water at 20 - 80℃;
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

3,4-dichlorophenylisocyanate
102-36-3

3,4-dichlorophenylisocyanate

1-(4-carboxyphenyl)-3-(3,4-dichlorophenyl)-1-methylurea

1-(4-carboxyphenyl)-3-(3,4-dichlorophenyl)-1-methylurea

Conditions
ConditionsYield
With sodium hydroxide89%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

4-(((benzyloxy)carbonyl)amino)benzoic acid
5330-71-2

4-(((benzyloxy)carbonyl)amino)benzoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 21℃; for 4h;89%
propylamine
107-10-8

propylamine

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4-(N-methylamino)-N-propylbenzamide
204973-14-8

4-(N-methylamino)-N-propylbenzamide

Conditions
ConditionsYield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 17h;87%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4-((tert-butoxycarbonyl)(methyl)amino)benzoic acid
263021-30-3

4-((tert-butoxycarbonyl)(methyl)amino)benzoic acid

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; N-methyl-p-aminobenzoic acid With sodium hydroxide In 1,4-dioxane; water at 20℃; for 48h;
Stage #2: With hydrogenchloride In water Cooling with ice bath;
87%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 48h; Reflux;69%
With triethylamine In 1,4-dioxane; water
With triethylamine In tetrahydrofuran at 20℃; for 24h;0.54 g
With triethylamine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;0.54 g
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

A

4-[N-methyl-N-(trifluoroacetyl)amino]benzoic acid
50734-07-1

4-[N-methyl-N-(trifluoroacetyl)amino]benzoic acid

B

p-benzoic anhydride
95485-14-6

p-benzoic anhydride

Conditions
ConditionsYield
In chloroform at 20℃; for 3h;A 84%
B 80 mg
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

(4-(methylamino)phenyl)methanol
181819-75-0

(4-(methylamino)phenyl)methanol

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at 0 - 25℃; for 6h;84%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 24h;65%
Multi-step reaction with 2 steps
1: acetyl chloride / 20 h / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: acetyl chloride / 20 h / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 0 °C
View Scheme
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

4-(N-acetyl-N-methylamino)benzoic acid
26961-99-9

4-(N-acetyl-N-methylamino)benzoic acid

Conditions
ConditionsYield
With acetic anhydride In pyridine84%
With acetic anhydride In pyridine84%
With acetic anhydride In pyridine84%
With acetic anhydride In pyridine84%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

benzotriazol-1-ol
2592-95-2

benzotriazol-1-ol

4-(methylamino)benzoic acid benzotriazol-1-yl ester
890402-74-1

4-(methylamino)benzoic acid benzotriazol-1-yl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 20℃;84%
carbon dioxide
124-38-9

carbon dioxide

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With phenylsilane In N,N-dimethyl acetamide at 60℃; for 4h; Reagent/catalyst; Sealed tube;84%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

2-amino-phenol
95-55-6

2-amino-phenol

2-(p-methylaminophenyl)benzoxazole

2-(p-methylaminophenyl)benzoxazole

Conditions
ConditionsYield
With polyphosphoric acid at 205℃; for 4h;83%
Stage #1: N-methyl-p-aminobenzoic acid; 2-amino-phenol at 205℃; for 4h;
Stage #2: With water at 20 - 80℃;
83%
N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

2,3-dichloro-5,6-dicyanopyrazine
56413-95-7

2,3-dichloro-5,6-dicyanopyrazine

4-[(3-chloro-5,6-dicyanopyrazin-2-yl)methylamino]benzoic acid
1246941-39-8

4-[(3-chloro-5,6-dicyanopyrazin-2-yl)methylamino]benzoic acid

Conditions
ConditionsYield
In tetrahydrofuran for 12h; Reflux;83%

10541-83-0Relevant articles and documents

Preparation of 4-methylamino-benzoic acid from Anaesthesin (4-aminobenzoic acid ethyl ester) via phase-transfer methylation of its amino group

Skupinski,Pichnej,Pakula,et al.

, p. 862 - 864 (1986)

-

Acetic Acid Accelerated Visible-Light Photoredox Catalyzed N-Demethylation of N,N-Dimethylaminophenyl Derivatives

Wu, Guolin,Li, Yazhen,Yu, Xuemei,Gao, Yu,Chen, Haijun

supporting information, p. 687 - 692 (2017/02/23)

N,N-Dimethylaminophenyl moiety is a common fragment in medicinal chemistry as several pharmaceuticals bearing this privileged motif are on the market and under clinical evaluation. Oxidative N-demethylation is generally regarded as the major metabolic pathway. However, pharmacokinetics, metabolites studies as well as the further structural modification are precluded by the impracticality of chemical synthesis. Here we report that acetic acid can significantly accelerate visible-light photoredox catalyzed N-demethylation of N,N-dimethylaminophenyl derivatives. This approach is easy for large scale reaction and even for potential industrial manufacture. (Figure presented.).

N-THIAZOL-2-YL-BENZAMIDE DERIVATIVES

-

Page/Page column 23, (2008/06/13)

The invention relates to N-thiazol-2-yl-benzamide derivatives of the formula I in the description wherein the variables are as defined in the claims. The compounds are A2A-receptor ligands, such as antagonists, agonists, reverse agonists or partial agonists, and are useful in the treatment of neurological and psychiatric disorders where an A2A-receptor is implicated.

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