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Methyl 4-aminobenzoate

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Name

Methyl 4-aminobenzoate

EINECS 210-598-7
CAS No. 619-45-4 Density 1.166 g/cm3
PSA 52.32000 LogP 1.63660
Solubility Soluble in alcohol and ether, slightly soluble in water Melting Point 110-113 °C
Formula C8H9NO2 Boiling Point 299.2 °C at 760 mmHg
Molecular Weight 151.165 Flash Point 154.9 °C
Transport Information N/A Appearance white to beige crystals or crystalline powder
Safety 26-37/39-36/37/39 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 619-45-4 (Methyl 4-aminobenzoate) Hazard Symbols HarmfulXn, IrritantXi
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;

Article Data 313

Methyl 4-aminobenzoate Synthetic route

619-50-1

4-nitrobenzoic acid methyl ester

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
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%
67-56-1

methanol

150-13-0

4-amino-benzoic acid

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
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%
20442-96-0

methyl 4-azidobenzoate

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
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%
150-13-0

4-amino-benzoic acid

poly(p-methyltriazenestyrene)

poly(p-methyltriazenestyrene)

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 20℃; for 96h;100%
106896-49-5

methyl 4-amino-3-bromobenzoate

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
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%

methyl 4-(((2-oxo-2-phenylethoxy)carbonyl)amino)benzoate

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
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%
67-56-1

methanol

201230-82-2

carbon monoxide

540-37-4

p-aminoiodobenzene

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
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%
150-13-0

4-amino-benzoic acid

616-38-6

carbonic acid dimethyl ester

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
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%
303120-71-0

2-[(4-methoxycarbonylphenylamino)methylene]malonic acid diethyl ester

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
With ethylenediamine In ethanol at 20℃; for 2.15h;95%
123876-56-2

methyl 4-(benzylamino)benzoate

619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
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.

Methyl 4-aminobenzoate Consensus Reports

Reported in EPA TSCA Inventory.   

Methyl 4-aminobenzoate Specification

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.

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