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CAS No.: | 619-45-4 |
---|---|
Name: | Methyl 4-aminobenzoate |
Article Data: | 313 |
Molecular Structure: | |
Formula: | C8H9NO2 |
Molecular Weight: | 151.165 |
Synonyms: | Benzoicacid, p-amino-, methyl ester (6CI,7CI,8CI);(4-(Methoxycarbonyl)phenyl)amine;4-(Carbomethoxy)aniline;4-(Methoxycarbonyl)aniline;4-Aminobenzenecarboxylicacid methyl ester;4-Aminobenzoic acid methyl ester;Methyl 4-aminobenzoate;Methyl 4-aminophenylcarboxylate;Methyl aniline-4-carboxylate;Methylp-aminobenzoate;NSC 3783;p-(Methoxycarbonyl)aniline;p-Aminobenzoic acidmethyl ester;p-Carbomethoxyaniline; |
EINECS: | 210-598-7 |
Density: | 1.166 g/cm3 |
Melting Point: | 110-113 °C |
Boiling Point: | 299.2 °C at 760 mmHg |
Flash Point: | 154.9 °C |
Solubility: | Soluble in alcohol and ether, slightly soluble in water |
Appearance: | white to beige crystals or crystalline powder |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 36/37/38-20/21/22 |
Safety: | 26-37/39-36/37/39 |
PSA: | 52.32000 |
LogP: | 1.63660 |
Conditions | Yield |
---|---|
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h; | 100% |
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h; | 100% |
With sodium tetrahydroborate; water In ethanol at 25℃; for 1h; Solvent; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
With thionyl chloride for 2h; Esterification; Heating; | 100% |
With acetyl chloride at 20℃; for 168h; Inert atmosphere; | 100% |
With thionyl chloride at 0 - 20℃; | 100% |
methyl 4-azidobenzoate
4-methoxycarbonyl aniline
Conditions | Yield |
---|---|
With sodium tetrahydroborate; tin bis(1,2-benzenethiolate) In tetrahydrofuran; phosphate buffer at 10℃; for 0.25h; pH=10; Reduction; | 100% |
With hydrazine hydrate In ethanol at 20℃; chemoselective reaction; | 99% |
With ammonium chloride; zinc In ethanol; water for 0.5h; Heating; | 98% |
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 20℃; for 96h; | 100% |
methyl 4-amino-3-bromobenzoate
4-methoxycarbonyl aniline
Conditions | Yield |
---|---|
With formic acid; tributyl-amine; 10-phenyl-10H-phenothiazine In acetonitrile at 20℃; for 49h; Inert atmosphere; UV-irradiation; | 100% |
With dihydroxyborane; potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 100℃; Suzuki Coupling; | 71% |
4-methoxycarbonyl aniline
Conditions | Yield |
---|---|
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2.5h; Sealed tube; Irradiation; Inert atmosphere; | 100% |
methanol
carbon monoxide
p-aminoiodobenzene
4-methoxycarbonyl aniline
Conditions | Yield |
---|---|
With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere; | 99% |
With triethylamine at 80℃; under 3750.38 Torr; for 3h; Autoclave; | 80% |
Conditions | Yield |
---|---|
With sulfuric acid for 18h; Reflux; Inert atmosphere; | 95% |
With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction; | 90% |
With sulfuric acid for 16h; Neat (no solvent); Reflux; | 89.64% |
2-[(4-methoxycarbonylphenylamino)methylene]malonic acid diethyl ester
4-methoxycarbonyl aniline
Conditions | Yield |
---|---|
With ethylenediamine In ethanol at 20℃; for 2.15h; | 95% |
methyl 4-(benzylamino)benzoate
4-methoxycarbonyl aniline
Conditions | Yield |
---|---|
With ammonium formate; zinc In ethylene glycol for 0.0333333h; microwave irradiation; | 93% |
With hydrogen; palladium on activated charcoal In ethanol for 24h; | 100 % Turnov. |
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The IUPAC name of p-Aminobenzoic acid methyl ester is methyl 4-aminobenzoate. With the CAS registry number 619-45-4 and EINECS 210-598-7, it is also named as Methyl aniline-4-carboxylate. The product's categories are Carboxylicester; Aromatic Esters; C8 to C9; Carbonyl Compounds; Esters; Aromatic Amino Acids; Peptide Synthesis; Unnatural Amino Acid Derivatives. It is white to beige crystals or crystalline powder which is soluble in alcohol and ether, slightly soluble in water. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.41; (4)ACD/LogD (pH 7.4): 1.41; (5)ACD/BCF (pH 5.5): 6.99; (6)ACD/BCF (pH 7.4): 6.99; (7)ACD/KOC (pH 5.5): 139.88; (8)ACD/KOC (pH 7.4): 140.01; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 29.54 Å2; (13)Index of Refraction: 1.565; (14)Molar Refractivity: 42.26 cm3; (15)Molar Volume: 129.6 cm3; (16)Surface Tension: 46.2 dyne/cm; (17)Enthalpy of Vaporization: 53.92 kJ/mol; (18)Vapour Pressure: 0.00121 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 3; (21)Exact Mass: 151.063329; (22)MonoIsotopic Mass: 151.063329; (23)Topological Polar Surface Area: 52.3; (24)Heavy Atom Count: 11; (25)Complexity: 139.
Preparation of p-Aminobenzoic acid methyl ester: It can be obtained by 4-amino-benzoic acid and methanol. This reaction which is a kind of Esterification needs reagent SOCl2 by heating. The reaction time is 2 hours. The yield is 100%.
Uses of p-Aminobenzoic acid methyl ester: It is used in organic synthesis and as dye intermediate. It also can react with 2-acetylamino-benzoic acid to get 4-(2-methyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid methyl ester. This reaction needs reagent PCl3 and solvent toluene by heating. The reaction time is 1.5 hours. The yield is 63%.
When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC)c1ccc(N)cc1
2. InChI:InChI=1/C8H9NO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,9H2,1H3
3. InChIKey:LZXXNPOYQCLXRS-UHFFFAOYAA
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 237mg/kg (237mg/kg) | Journal of Medicinal Chemistry. Vol. 17, Pg. 900, 1974. |