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41263-74-5 Usage

Chemical Properties

Yellow Solid

Uses

4-(Methylamino)-3-nitrobenzoic Acid (cas# 41263-74-5) is a compound useful in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 41263-74-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,2,6 and 3 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 41263-74:
(7*4)+(6*1)+(5*2)+(4*6)+(3*3)+(2*7)+(1*4)=95
95 % 10 = 5
So 41263-74-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H8N2O4/c1-9-6-3-2-5(8(11)12)4-7(6)10(13)14/h2-4,9H,1H3,(H,11,12)/p-1

41263-74-5SDS

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-(Methylamino)-3-Nitrobenzoic Acid

1.2 Other means of identification

Product number -
Other names 4-(Methylamino)-3-nitrobenzoic Acid

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:41263-74-5 SDS

41263-74-5Synthetic route

methylamine
74-89-5

methylamine

4-chloro-3-nitrobenzoate
96-99-1

4-chloro-3-nitrobenzoate

4-(methylamino)-3-nitrobenzoic acid
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%
3-fluoro-4-nitrobenzoic acid
403-21-4

3-fluoro-4-nitrobenzoic acid

methylamine
74-89-5

methylamine

4-(methylamino)-3-nitrobenzoic acid
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%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

methylamine
74-89-5

methylamine

4-(methylamino)-3-nitrobenzoic acid
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%
4-bromo-3-nitrobenzoic acid
6319-40-0

4-bromo-3-nitrobenzoic acid

methylamine
74-89-5

methylamine

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

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With D-myo-inositol; copper; caesium carbonate In water at 100℃;92%
4-chloro-3-nitrobenzoate
96-99-1

4-chloro-3-nitrobenzoate

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

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With methylamine In water86%
4-methylamino-3-nitro-benzoic acid methyl ester
36242-50-9

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

4-(methylamino)-3-nitrobenzoic acid
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%
3,4-dinitrobenzoic acid
528-45-0

3,4-dinitrobenzoic acid

methylamine
74-89-5

methylamine

4-(methylamino)-3-nitrobenzoic acid
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%
nitro acetate
591-09-3

nitro acetate

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

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

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

4-(methylamino)-3-nitrobenzoic acid

ethyl 4-(methylamino)-3-nitrobenzoate
71254-71-2

ethyl 4-(methylamino)-3-nitrobenzoate

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

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With potassium hydroxide
4-(N,N-dimethylamino)-3-nitrobenzoic acid
28096-56-2

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

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

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With potassium permanganate; sodium carbonate
With nitrosyl acetate
4-dimethylamino-3-nitrobenzaldehyde
59935-39-6

4-dimethylamino-3-nitrobenzaldehyde

4-(methylamino)-3-nitrobenzoic acid
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
sulfuric acid
7664-93-9

sulfuric acid

4-(methoxycarbonyl)-2-nitro-N,N-dimethylaniline
82080-46-4

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

nitric acid
7697-37-2

nitric acid

A

4-(methylamino)-3-nitrobenzoic acid
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℃;
4-(dimethylamino)-3-nitrobenzonitrile
19005-63-1

4-(dimethylamino)-3-nitrobenzonitrile

4-(methylamino)-3-nitrobenzoic acid
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

4-dimethylamino-3-nitro-benzaldehyde-oxime

4-(methylamino)-3-nitrobenzoic acid
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
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

4-(methylamino)-3-nitrobenzoic 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
ethyl 4-ethoxy-3-nitrobenzoate
937625-32-6

ethyl 4-ethoxy-3-nitrobenzoate

4-(methylamino)-3-nitrobenzoic acid
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
methyl 3-nitro-4-chlorobenzoate
14719-83-6

methyl 3-nitro-4-chlorobenzoate

4-(methylamino)-3-nitrobenzoic acid
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
4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

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

4-(methylamino)-3-nitrobenzoic acid

4-methylamino-3-nitro-benzoic acid chloride
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%
(R)-piperidin-3-ylcarbamic acid tert-butyl ester
309956-78-3

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

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

4-(methylamino)-3-nitrobenzoic acid

1,1-dimethylethyl ((3R)-1-{[4-(methylamino)-3-nitrophenyl]carbonyl}-3-piperidinyl)carbamate
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%
4-(methylamino)-3-nitrobenzoic acid
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

3-amino-4-(methylamino)benzoic 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%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

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

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

4-(methylamino)-3-nitrobenzoic acid

ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]propanoate hydrochloride
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%
4-(methylamino)-3-nitrobenzoic acid
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

C8H7ClN2O4

C8H7ClN2O4

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

methanol

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

4-(methylamino)-3-nitrobenzoic acid

4-methylamino-3-nitro-benzoic acid methyl ester
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%
4-(methylamino)-3-nitrobenzoic acid
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

4-bromo-aniline
106-40-1

4-bromo-aniline

N-(4-bromo-phenyl)-4-methylamino-3-nitro-benzamide
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%
ethanol
64-17-5

ethanol

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

4-(methylamino)-3-nitrobenzoic acid

3-amino-4-(methylamino)benzoic acid
66315-15-9

3-amino-4-(methylamino)benzoic acid

Conditions
ConditionsYield
palladium-carbon61%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

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

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

4-(methylamino)-3-nitrobenzoic acid

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

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%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

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

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

4-(methylamino)-3-nitrobenzoic acid

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

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%
ethanol
64-17-5

ethanol

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

4-(methylamino)-3-nitrobenzoic acid

ethyl 4-(methylamino)-3-nitrobenzoate
71254-71-2

ethyl 4-(methylamino)-3-nitrobenzoate

Conditions
ConditionsYield
With sulfuric acid
4-(methylamino)-3-nitrobenzoic acid
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

acetic anhydride
108-24-7

acetic anhydride

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

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

Conditions
ConditionsYield
With sulfuric acid
4-(methylamino)-3-nitrobenzoic acid
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

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

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

4-(methylamino)-3-nitrobenzoic acid

3-amino-4-(methylamino)benzamide
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

41263-74-5Relevant articles and documents

Molecular modeling studies, synthesis and biological evaluation of dabigatran analogues as thrombin inhibitors

Dong, Ming-Hui,Chen, Hai-Feng,Ren, Yu-Jie,Shao, Fang-Ming

, p. 73 - 84 (2016)

In this work, 48 thrombin inhibitors based on the structural scaffold of dabigatran were analyzed using a combination of molecular modeling techniques. We generated three-dimensional quantitative structure-activity relationship (3D-QSAR) models based on three alignments for both comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) to highlight the structural requirements for thrombin protein inhibition. In addition to the 3D-QSAR study, Topomer CoMFA model also was established with a higher leave-one-out cross-validation q2 and a non-cross-validation r2, which suggest that the three models have good predictive ability. The results indicated that the steric, hydrophobic and electrostatic fields play key roles in QSAR model. Furthermore, we employed molecular docking and re-docking simulation explored the binding relationship of the ligand and the receptor protein in detail. Molecular docking simulations identified several key interactions that were also indicated through 3D-QSAR analysis. On the basis of the obtained results, two compounds were designed and predicted by three models, the biological evaluation in vitro (IC50) demonstrated that these molecular models were effective for the development of novel potent thrombin inhibitors.

A chemical approach for the synthesis of the DNA-binding domain of the oncoprotein MYC

Calo-Lapido, Renata,Penas, Cristina,Jiménez-Balsa, Adrián,Vázquez, M. Eugenio,Mascare?as, José L.

, p. 6748 - 6752 (2019)

We describe the first chemical synthesis of a functional mutant of the DNA binding domain of the oncoprotein MYC, using two alternative strategies which involve either one or two Native Chemical Ligations (NCLs). Both routes allowed the efficient synthesis of a miniprotein which is capable of heterodimerizing with MAX, and replicate the DNA binding of the native protein. The versatility of the reported synthetic approach enabled the straightforward preparation of MYC and Omomyc analogues, as well as fluorescently labeled derivatives.

Design, synthesis and biological activity evaluation of novel methyl substituted benzimidazole derivatives

Liu, Qianqian,Ren, Yujie,Zhang, Tianrong

, (2020/03/03)

Ten new dabigatran derivatives (7a–j) with high docking scoring were designed, synthesised and biologically evaluated. The inhibitory in vitro activity of these compounds on thrombin was evaluated on the basis of preliminary activity screening results. The IC50 values of compounds 7a, 7d and 7j were 1.92, 2.17 and 1.54 nM, respectively, and are equivalent to the dabigatran (IC50 = 1.20 nM). Therefore, the most active compound, 7j, was selected to further investigate the anticoagulant activity in rats. Compound 7j presented excellent in vivo inhibitory effects on arteriovenous thrombosis, and the inhibition rate was (84.19 ± 1.14) %. The anticoagulant activity of compound 7k synthesised in the previous work was evaluated in vivo, and its inhibition rate was (85.58 ± 2.89) %. This rate was nearly equivalent to that of dabigatran (85.07 ± 0.61) %. Results indicated that compounds 7a, 7d, 7j and 7k can be further studied as novel antithrombin drug candidates.

Computer-aid drug design, synthesis, and anticoagulant activity evaluation of novel dabigatran derivatives as thrombin inhibitors

Huang, Shanshan,Ren,Peng, Xiuxiu,Qian, Pingping,Meng, Lingwei

, (2019/07/05)

In this study, computer-aided drug design techniques were adopted to explore the structural and chemical features for dabigatran and design novel derivatives. The built 3D-QSAR models demonstrated significant statistical quality and excellent predictive ability by internal and external validation. Based on QSAR information, 11 novel dabigatran derivatives (12a–12k) were designed and predicted, then ADME prediction and molecular docking were performed. Furthermore, all designed compounds were synthesized and characterized by 1H NMR, 13C NMR and HR-MS. Finally, they were evaluated for anticoagulant activity in vitro. The activity results showed that the 10 obtained compounds exhibited comparable activity to the reference dabigatran (IC50 = 9.99 ± 1.48 nM), except for compound 12i. Further analysis on molecular docking was performed on three compounds (12a, 12c and 12g) with better activity (IC50 = 11.19 ± 1.70 nM, IC50 = 10.94 ± 1.85 nM and IC50 = 11.19 ± 1.70 nM). MD simulations (10 ns) were carried out, and their binding free energies were calculated, which showed strong hydrogen bond and pi–pi stacking interactions with key residues Gly219, Asp189 and Trp60D. The 10 novel dabigatran derivatives obtained can be further studied as anticoagulant candidate compounds.

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