4-Methylamino-3-nitrobenzoic acid supplier

Name
4-(METHYLAMINO)-3-NITROBENZOIC ACID
EINECS 609-904-5
CAS No. 41263-74-5
Article Data38
CAS DataBase
Density 1.472 g/cm³
Solubility
Melting Point >300 °C
Formula C₈H₈N₂O₄
Boiling Point 393.7 °C at 760 mmHg
Molecular Weight 196.163
Flash Point 191.9 °C
Transport Information
Appearance Yellow solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-(Methylamino)-3-nitrobenzoicacid;NSC 138300;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With methylamine In water	86%

: 36242-50-9
4-methylamino-3-nitro-benzoic acid methyl ester

: 41263-74-5
4-(methylamino)-3-nitrobenzoic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium hydroxide

: 28096-56-2
4-(N,N-dimethylamino)-3-nitrobenzoic acid

: 41263-74-5
4-(methylamino)-3-nitrobenzoic acid

Conditions

Conditions	Yield
With potassium permanganate; sodium carbonate
With nitrosyl acetate

: 59935-39-6
4-dimethylamino-3-nitrobenzaldehyde

: 41263-74-5
4-(methylamino)-3-nitrobenzoic acid

Conditions

Conditions	Yield
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

Conditions	Yield
at 70 - 75℃;

...Expand

: 19005-63-1
4-(dimethylamino)-3-nitrobenzonitrile

: 41263-74-5
4-(methylamino)-3-nitrobenzoic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
palladium-carbon	61%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sulfuric acid

: 41263-74-5
4-(methylamino)-3-nitrobenzoic acid

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

Conditions

Conditions	Yield
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

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 2: NH3 3: H2 / Pd/C / ethanol View Scheme

4-Methylamino-3-nitrobenzoic acid Chemical Properties

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

Product Name

4-(METHYLAMINO)-3-NITROBENZOIC ACID

Synthetic route

4-Methylamino-3-nitrobenzoic acid Chemical Properties

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