Methyl 4-amino-3-nitrobenzoate
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Methyl 4-amino-3-nitrobenzoate
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CAS No:
3987-92-6
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Formula:
C8H8N2O4
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Chemical Name:
Methyl 4-amino-3-nitrobenzoate
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Synonyms:
Benzoic acid,4-amino-3-nitro-,methyl ester;4-Methoxycarbonyl-2-nitroaniline;Methyl 4-amino-3-nitrobenzoate;4-Amino-3-nitrobenzoic acid methyl ester;Methyl 3-nitro-4-aminobenzoate;1-Amino-2-nitro-4-(methoxycarbonyl)benzene;2-Nitro-4-carbomethoxyaniline
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CAS No:
Safety Information
Xi: Irritant;
P264, P270, P301+P312, P330, P501
H302
|Warning|H302 (95%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory.
Methyl 4-amino-3-nitrobenzoate Use and Manufacturing
To a suspension of 4-amino-3-nitrobenzoic acid (50 g, 270 mmol, 1 equiv) in MEOH (600 mi) at room temperature was added SOCI2 (20 ML, 270 mmol, 1 equiv) dropwise. The resulting suspension was refluxed for 16 h then cooled to room temperature. The suspension was filtered off to give methyl-4-amino-3-nitrobenzoate (D1) (53g, 100percent) as a yellow solid which was used in the next step without further purification. [M+H] + = 197.3, RT = 2. 42 min.Description 1Methyl 4-amino-3-nitrobenzoate (D1); To a suspension of 4-amino-3-nitrobenzoic acid (available commercially from Aldrich) (50 g, 270 mmol, 1 equiv) in MeOH (600 ml) at room temperature was added SOCIPreparaton ofJ^-(4-(methoxymethyl)-2-nitrophenyl)~lS^-methylpyrM a. methyl 4-amino-3-nitrobenzoate Thionyl chloride (19.4g, 164.85 mmol) was added to a solution of 4-amino-3-nitrobenzoic acid (20g, 109.89 mmol) in methanol (200mL) at 0 °C. The resulting mixture was then refiuxed for 12h. The reaction mixture was allowed to cool to room temperature. The yellow solid precipitated was filtered and dried to afford the title compound (22g, yield: 100percent) as a solid. IH- NMR (CDC14-aminobenzoic acid (i.e., compound 1.4.50 g, 24.7 mmol), anhydrous methanol (80 mL), (5.38 mL, 74.1 mmol, 3 equiv) was slowly added dropwise with a constant-pressure dropping funnel. After completion of the dropwise addition, the mixture was further stirred at 0 ° C for 30 minutes, and the mixture was cooled to 0 ° C. , Heated to 50 reaction 4h, a large number of yellow solids generated, filtration, the filtrate of methanol evaporated, add 30mL of water and 30mL of ethyl acetate, liquid, dry the organic layer with anhydrous sodium sulfate, evaporated solvent To give a yellow solid which was combined with the previous filter cake and dried to give compound 2a as a yellow solid, 4.32 g, 89.2percent yield. Melting point: 181.9-182.7 ° C.The commercial compound 4 (4.50g, 24.7mmol) was dissolved in methanol (80mL). The reaction was cooled to 0°C, and thionyl chloride (5.38mL, 74.1mmol, 3 equiv) was added dropwise. The reaction mixture was stirred at 0°C for 30min and was heated to 50°C for 4h. The precipitate formed on cooling was collected by filtration. The solvent was removed under reduced pressure. The residue was dissolved with water and extracted with ethyl acetate. The organic layer was dried over anhydrous NaStep 1 4-Amino-3-nitro-benzoic acid methyl esterTo a mixture of 4-amino-3-nitro-benzoic acid (10.0 g, 54.9 mm0l) suspended in methanol (150 mL) was added thionyl chloride (3.99 mL, 54.9 mmol). The mixture was heated to reflux overnight, then cooled to room temperature and filtered. The solid recovered by filtration was rinsed with cold methanol and dried to give 8.68 g (81percent) of 4-amino-3-nitro-benzoic acid methyl ester.
Computed Properties
Molecular Weight:196.16
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:196.04840674
Monoisotopic Mass:196.04840674
Topological Polar Surface Area:98.1
Heavy Atom Count:14
Complexity:238
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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