Methyl 4-aminobenzoate

Base Information

• Chemical Name: Methyl 4-aminobenzoate
• CAS No.: 619-45-4
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.165
• Hs Code.: 29224995
• European Community (EC) Number: 210-598-7
• NSC Number: 3783
• UNII: GC4GA4E73E
• DSSTox Substance ID: DTXSID7060704
• Nikkaji Number: J45.061H
• Wikidata: Q63409584
• ChEMBL ID: CHEMBL1927048
• Mol file: 619-45-4.mol

Synonyms:methyl 4-aminobenzoate;methyl 4-aminobenzoate hydrobromide;methyl 4-aminobenzoate hydrochloride;methyl 4-aminobenzoate sulfate (2:1);p-aminobenzoic acid methyl ester

Chemical Property of Methyl 4-aminobenzoate

Chemical Property:

• Appearance/Colour: white to beige crystals or crystalline powder
• Vapor Pressure: 0.00121mmHg at 25°C
• Melting Point: 110-113 °C
• Refractive Index: 1.5810 (estimate)
• Boiling Point: 299.2 °C at 760 mmHg
• PKA: pK1:2.38(＋1) (25°C)
• Flash Point: 154.9 °C
• PSA: 52.32000
• Density: 1.166 g/cm³
• LogP: 1.63660
• Storage Temp.: Store below +30°C.
• Solubility.: 3.82g/l
• Water Solubility.: Soluble in alcohol and ether. Slightly soluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

4-AminobenzoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)N
• Uses: Methyl 4-aminobenzoate is used in the synthesis of guanidine alkaloids, (±)-martinelline and (±)-martinellic acid by a protic acid catalyzed hetero Diels-Alder coupling reaction with N-Cbz 2-pyrroline. It is also used in organic synthesis and acts as a dye intermediate. Further, it is used to prepare 4-(2-methyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid methyl ester by reacting with 2-acetylamino-benzoic acid. 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.

Technology Process of Methyl 4-aminobenzoate

There total 144 articles about Methyl 4-aminobenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl 4-amino-3-bromobenzoate (106896-49-5) → 4-methoxycarbonyl aniline (619-45-4)

Guidance literature:

With formic acid; tributyl-amine; 10-phenyl-10H-phenothiazine; In acetonitrile; at 20 ℃; for 49h; Inert atmosphere; UV-irradiation;

DOI:10.1039/c5cc04677g

Reference yield: 93.0%

methyl 4-iodobenzoate (619-44-3) → 4-methoxycarbonyl aniline (619-45-4)

Guidance literature:

With sodium azide; copper; L-proline; In water; dimethyl sulfoxide; at 150 ℃; for 0.583333h; under 37503.8 Torr; chemoselective reaction; Flow reactor;

DOI:10.1002/adsc.201701539

Reference yield: 91.0%

4-methoxycarbonylphenyl bromide (619-42-1) → 4-methoxycarbonyl aniline (619-45-4)

Guidance literature:

4-methoxycarbonylphenyl bromide; With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; at 50 ℃; for 6h;

With hydrogenchloride; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ol050141b

upstream raw materials:

diazomethane

4-amino-benzoic acid

4-nitrobenzoic acid methyl ester

methanol

Downstream raw materials:

1-(4-amino-phenyl)-2-[2]pyridyl-ethanone

methyl 4-acetamidobenzoate

N-(4-methoxycarbonyl-phenyl)-glycine-(4-methoxycarbonyl-anilide)

chloro-N-(4-methoxycarbonylphenyl)acetamide

Refernces

• 1、 Eom, Taejun,Khan, Anzar. "Hypersensitive azobenzenes: Facile synthesis of clickable and cleavable azo linkers with tunable and high reducibility". . p. 420 - 424. Retrieved 2020.
• 2、 Doriguetto, Antonio C.,De Paula Silva, Carlos H.T.,Rando, Daniela G.,Ferreira, Elizabeth I.,Ellena, Javier. "A new monoclinic polymorph of methyl p-aminobenzoate". . p. o69-o71. Retrieved 2004.
• 3、 Bartling, Stephan,Beller, Matthias,Chandrashekhar, Vishwas G.,Jagadeesh, Rajenahally V.,Rabeah, Jabor,Rockstroh, Nils,Senthamarai, Thirusangumurugan. "A “universal” catalyst for aerobic oxidations to synthesize (hetero)aromatic aldehydes, ketones, esters, acids, nitriles, and amides". supporting information. p. 508 - 531. Retrieved 2022/02/11.
• 4、 Wang, Tao,Hoffmann, Marvin,Dreuw, Andreas,Hasagi?, Edina,Hu, Chao,Stein, Philipp M.,Witzel, Sina,Shi, Hongwei,Yang, Yangyang,Rudolph, Matthias,Stuck, Fabian,Rominger, Frank,Kerscher, Marion,Comba, Peter,Hashmi, A. Stephen K.. "A Metal-Free Direct Arene C?H Amination". supporting information. p. 2783 - 2795. Retrieved 2021/04/05.