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41263-74-5

Basic Information
CAS No.: 41263-74-5
Name: 4-Methylamino-3-nitrobenzoic acid
Molecular Structure:
Molecular Structure of 41263-74-5 (4-Methylamino-3-nitrobenzoic acid)
Formula: C8H8N2O4
Molecular Weight: 196.16
Synonyms: 4-(Methylamino)-3-nitrobenzoicacid;NSC 138300;
EINECS: 609-904-5
Density: 1.472 g/cm3
Melting Point: >300 °C
Boiling Point: 393.7 °C at 760 mmHg
Flash Point: 191.9 °C
Solubility:
Appearance: Yellow solid
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 95.15000
LogP: 1.93090
Synthetic route
74-89-5

methylamine

96-99-1

4-chloro-3-nitrobenzoate

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
In water at 100℃; for 14h;100%
In water at 80℃; for 5h;100%
Stage #1: methylamine; 4-chloro-3-nitrobenzoate In water for 4h; Reflux;
Stage #2: With sulfuric acid In water at 20℃; pH=2; Product distribution / selectivity;
95.5%
403-21-4

3-fluoro-4-nitrobenzoic acid

74-89-5

methylamine

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
Stage #1: 3-fluoro-4-nitrobenzoic acid; methylamine In DMF (N,N-dimethyl-formamide); water at 20℃; for 1h;
Stage #2: With potassium hydrogensulfate In water pH=2;
100%
453-71-4

3-nitro-4-fluorobenzoic acid

74-89-5

methylamine

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
In methanol; ethanol at 20℃; for 2h;99%
In methanol at 20℃; for 18h;99%
In methanol at 20℃; for 10h;98%
6319-40-0

4-bromo-3-nitrobenzoic acid

74-89-5

methylamine

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With D-myo-inositol; copper; caesium carbonate In water at 100℃;92%
96-99-1

4-chloro-3-nitrobenzoate

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With methylamine In water86%
36242-50-9

4-methylamino-3-nitro-benzoic acid methyl ester

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
Stage #1: 4-methylamino-3-nitro-benzoic acid methyl ester With lithium hydroxide In tetrahydrofuran; water at 20℃; for 16h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=Ca. 5;
84%
With lithium hydroxide In tetrahydrofuran; water at 20℃; for 16h;84%
With water; lithium hydroxide In tetrahydrofuran at 20℃; for 16h;84%
528-45-0

3,4-dinitrobenzoic acid

74-89-5

methylamine

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
Stage #1: 3,4-dinitrobenzoic acid; methylamine With triethylamine In methanol; ethanol at 20℃; for 24h;
Stage #2: With acetic acid In water
81%
591-09-3

nitro acetate

28096-56-2

4-(N,N-dimethylamino)-3-nitrobenzoic acid

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

71254-71-2

ethyl 4-(methylamino)-3-nitrobenzoate

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With potassium hydroxide
28096-56-2

4-(N,N-dimethylamino)-3-nitrobenzoic acid

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With potassium permanganate; sodium carbonate
With nitrosyl acetate
59935-39-6

4-dimethylamino-3-nitrobenzaldehyde

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With potassium permanganate; sodium carbonate
Multi-step reaction with 4 steps
1: alkali; hydroxylamine hydrochloride
2: acetic acid anhydride; sodium acetate
3: NaOH-solution; alcohol
4: potassium permanganate; natrium carbonate
View Scheme
7664-93-9

sulfuric acid

82080-46-4

4-(methoxycarbonyl)-2-nitro-N,N-dimethylaniline

7697-37-2

nitric acid

A

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

B

3.5-dinitro-4-methylnitramino-benzoic acid methyl ester

3.5-dinitro-4-methylnitramino-benzoic acid methyl ester

Conditions
ConditionsYield
at 70 - 75℃;
19005-63-1

4-(dimethylamino)-3-nitrobenzonitrile

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH-solution; alcohol
2: potassium permanganate; natrium carbonate
View Scheme

4-dimethylamino-3-nitro-benzaldehyde-oxime

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid anhydride; sodium acetate
2: NaOH-solution; alcohol
3: potassium permanganate; natrium carbonate
View Scheme
619-84-1

p-N,N-dimethylaminobenzoic acid

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HNO3+H2SO4 / 0 °C
2: potassium permanganate; natrium carbonate
View Scheme
937625-32-6

ethyl 4-ethoxy-3-nitrobenzoate

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: alcohol / 130 - 140 °C / im Druckrohr
2: KOH-solution
View Scheme
14719-83-6

methyl 3-nitro-4-chlorobenzoate

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N,N-dimethyl-formamide / 70 - 90 °C / Inert atmosphere
2.1: lithium hydroxide / tetrahydrofuran; water / 16 h / 20 °C
2.2: pH Ca. 5
View Scheme
Multi-step reaction with 2 steps
1: tetrahydrofuran; N,N-dimethyl-formamide / 20 - 90 °C / Inert atmosphere
2: lithium hydroxide / tetrahydrofuran; water / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide; tetrahydrofuran / 70 - 90 °C
2: lithium hydroxide; water / tetrahydrofuran / 16 h / 20 °C
View Scheme
456-22-4

4-Fluorobenzoic acid

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid / 10 h / 20 °C
2: methanol / 10 h / 20 °C
View Scheme
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

82357-48-0

4-methylamino-3-nitro-benzoic acid chloride

Conditions
ConditionsYield
With thionyl chloride Chlorination; Heating;100%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane Reflux;100%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 30℃;100%
309956-78-3

(R)-piperidin-3-ylcarbamic acid tert-butyl ester

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

1549812-10-3

1,1-dimethylethyl ((3R)-1-{[4-(methylamino)-3-nitrophenyl]carbonyl}-3-piperidinyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;100%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;100%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;100%
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

66315-15-9

3-amino-4-(methylamino)benzoic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 2h;99%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃;99%
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 48h;36.5%
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

1187067-68-0

ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]propanoate hydrochloride

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; Solvent; Reagent/catalyst;95.2%
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

C8H7ClN2O4

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide; toluene at 0 - 70℃;82%
67-56-1

methanol

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

36242-50-9

4-methylamino-3-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid for 6h; Reflux;77%
Stage #1: methanol; 4-(methylamino)-3-nitrobenzoic acid With hydrogenchloride In N,N-dimethyl-formamide for 10h; Reflux;
Stage #2: With sodium hydrogencarbonate In water
32%
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

106-40-1

4-bromo-aniline

1003098-13-2

N-(4-bromo-phenyl)-4-methylamino-3-nitro-benzamide

Conditions
ConditionsYield
Stage #1: 4-(methylamino)-3-nitrobenzoic acid With pyridine; 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane
Stage #2: 4-bromo-aniline In dichloromethane for 16h;
68%
64-17-5

ethanol

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

66315-15-9

3-amino-4-(methylamino)benzoic acid

Conditions
ConditionsYield
palladium-carbon61%
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate hydrochloride

Conditions
ConditionsYield
Stage #1: 4-(methylamino)-3-nitrobenzoic acid With thionyl chloride In N,N-dimethyl-formamide for 0.75h; Reflux;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With triethylamine In tetrahydrofuran at 20 - 60℃;
Stage #3: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity;
47.2%
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate hydrochloride

Conditions
ConditionsYield
Stage #1: 4-(methylamino)-3-nitrobenzoic acid With thionyl chloride In N,N-dimethyl-formamide for 0.75h; Reflux;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With triethylamine In tetrahydrofuran at 20 - 60℃;
Stage #3: With hydrogenchloride In ethyl acetate Product distribution / selectivity;
47.2%
64-17-5

ethanol

41263-74-5

4-(methylamino)-3-nitrobenzoic acid

71254-71-2

ethyl 4-(methylamino)-3-nitrobenzoate

Conditions
ConditionsYield
With sulfuric acid
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

108-24-7

acetic anhydride

4-(acetyl-methyl-amino)-3-nitro-benzoic acid

Conditions
ConditionsYield
With sulfuric acid
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

1-methyl-2-(4-phenoxy-phenyl)-1H-benzoimidazole-5-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: SOCl2
2: NH3
3: H2 / Pd/C / ethanol
4: 65 percent / Na2S2O5 / dimethylformamide / 100 °C
View Scheme
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

39033-67-5

3-amino-4-(methylamino)benzamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2
2: NH3
3: H2 / Pd/C / ethanol
View Scheme
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    Product Name: 4-(METHYLAMINO)-3-NITROBENZOIC ACID Synonyms: 4-(METHYLAMINO)-3-NITROBENZOIC ACID;NSC 138300;4-(MethylaMino)-3-nitrobenzoic acid 98%;Benzoic acid, 4-(MethylaMino)-3-nitro-;Dabigatran Etexilate Intermediate 5 CAS: 41263-74-5

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Chemistry

Product Name: 4-Methylamino-3-nitrobenzoic acid (CAS NO.41263-74-5)

Molecular Formula: C8H8N2O4
Molecular Weight: 196.16g/mol
Mol File: 41263-74-5.mol
Boiling point: 393.7 °C at 760 mmHg
Flash Point: 191.9 °C
Density: 1.472 g/cm3
Index of Refraction: 1.662 
Molar Refractivity: 49.33 cm3 
Molar Volume: 133.2 cm3 
Surface Tension: 68.7 dyne/cm
Enthalpy of Vaporization: 67.88 kJ/mol
Vapour Pressure: 6.62E-07 mmHg at 25°C
XLogP3-AA: 1.9
H-Bond Donor: 2
H-Bond Acceptor: 5
Structure Descriptors of 4-Methylamino-3-nitrobenzoic acid (CAS NO.41263-74-5):
  IUPAC Name: 4-(methylamino)-3-nitrobenzoic acid
  Canonical SMILES: CNC1=C(C=C(C=C1)C(=O)O)[N+](=O)[O-]
  InChI: InChI=1S/C8H8N2O4/c1-9-6-3-2-5(8(11)12)4-7(6)10(13)14/h2-4,9H,1H3,(H,11,12) 
  InChIKey: KSMLIIWEQBYUKA-UHFFFAOYSA-N