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274186

Sigma-Aldrich

Methyl 4-aminobenzoate

98%

Synonym(s):

(4-(Methoxycarbonyl)phenyl)amine, 4-(Carbomethoxy)aniline, 4-Aminobenzenecarboxylic acid methyl ester, 4-Aminobenzoic acid methyl ester, Methyl aniline-4-carboxylate, Methyl p-aminobenzoate, p-Aminobenzoic acid methyl ester, p-Carbomethoxyaniline

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About This Item

Linear Formula:
H2NC6H4CO2CH3
CAS Number:
619-45-4
Molecular Weight:
151.16
Beilstein:
775913
EC Number:
210-598-7
MDL number:
MFCD00007891
UNSPSC Code:
12352100
PubChem Substance ID:
24856569
NACRES:
NA.22

Assay

98%

form

solid

mp

110-111 °C (lit.)

SMILES string

COC(=O)c1ccc(N)cc1

InChI

1S/C8H9NO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,9H2,1H3

InChI key

LZXXNPOYQCLXRS-UHFFFAOYSA-N

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General description

The catalytic oxidation of methyl 4-aminobenzoate by hydrogen peroxide was studied.

Application

Methyl 4-aminobenzoate was used in the syntheses of guanidine alkaloids, (±)-martinelline and (±)-martinellic acid by a protic acid catalyzed hetero Diels-Alder coupling reaction with N-Cbz 2-pyrroline.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Wipapan Pongcharoen et al.
Chemical & pharmaceutical bulletin, 55(11), 1647-1648 (2007-11-06)
Chemical investigation of the wood-decayed fungus Xylaria sp. BCC 9653 has led to the isolation of a new methyl aminobenzoate (1) together with eleven known compounds. The structures were established by analysis of spectroscopic data. Cytochalasin D (2), one of
Beate Priewisch et al.
The Journal of organic chemistry, 70(6), 2350-2352 (2005-03-12)
[reaction: see text] Reaction conditions are described for the oxidation of anilines furnishing nitrosoarenes and the synthesis of unsymmetrically substituted azobenzenes. In a comparative study, the catalytic oxidation of methyl 4-aminobenzoate by hydrogen peroxide was investigated, and SeO(2) proved to
David A Powell et al.
Organic letters, 4(17), 2913-2916 (2002-08-17)
[reaction: see text] A concise synthesis of the guanidine alkaloids, (+/-)-martinelline and (+/-)-martinellic acid, using a protic acid catalyzed 2:1 hetero Diels-Alder coupling reaction between N-Cbz 2-pyrroline and methyl 4-aminobenzoate, is described. Protic acid catalysis, rather than Lewis acid catalysis
W Addicks et al.
Pharmaceutical research, 7(10), 1048-1054 (1990-10-01)
Stainless-steel templates of various thicknesses (75, 200, 800, and 1600 microns) were used to apply propylene glycol/water gels containing methyl or propyl p-aminobenzoates to silicone rubber membranes, and drug delivery was studied with the use of the Bronaugh diffusion cell
C B Lalor et al.
Journal of pharmaceutical sciences, 84(6), 673-676 (1995-06-01)
The major influence on the rate of drug transfer out of its vehicle and into the skin is the thermodynamic activity of the drug within its formulation. This study addresses certain thermodynamic dependencies of topical delivery in a model system.
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