4-(Methylamino)benzoic acid

Base Information

• Chemical Name: 4-(Methylamino)benzoic acid
• CAS No.: 10541-83-0
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.165
• Hs Code.: 2922499990
• European Community (EC) Number: 234-121-7
• NSC Number: 102506
• UNII: ARU98Z0OZY
• DSSTox Substance ID: DTXSID8065117
• Nikkaji Number: J139.221B
• Wikidata: Q27107471
• Metabolomics Workbench ID: 67816
• ChEMBL ID: CHEMBL3098156
• Mol file: 10541-83-0.mol

Synonyms:4-methylaminobenzoic acid;p-methylaminobenzoic acid

Chemical Property of 4-(Methylamino)benzoic acid

Chemical Property:

• Appearance/Colour: white to beige powder
• Vapor Pressure: 0.000122mmHg at 25°C
• Melting Point: 160-162 °C(lit.)
• Refractive Index: 1.5810 (estimate)
• Boiling Point: 321.6 °C at 760mmHg
• PKA: 5.04(at 25℃)
• Flash Point: 148.3 °C
• PSA: 49.33000
• Density: 1.244 g/cm³
• LogP: 1.49950
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Slightly soluble. Soluble in alcohol.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

4-Methylaminobenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi, N
• Hazard Codes: Xn,Xi,N
• Statements: 22-43-36/37/38-51/53-40
• Safety Statements: 36/37-37/39-26-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Aminobenzoic Acids
• Canonical SMILES: CNC1=CC=C(C=C1)C(=O)O
• Description: 4-(Methylamino) benzoic acid is an important intermediate for production of pharmaceutical products, dyes, flavors and preservatives.
• Uses: 4-(Methylamino)benzoic acid important for the preparation of other pharmaceutical products, dyes, flavors, and preservatives. .For the preparation of medicines and other fine chemicals.

Technology Process of 4-(Methylamino)benzoic acid

There total 32 articles about 4-(Methylamino)benzoic acid 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: 96.0%

p-N,N-dimethylaminobenzoic acid (619-84-1) → N-methyl-p-aminobenzoic acid (10541-83-0,937737-33-2)

Guidance literature:

p-N,N-dimethylaminobenzoic acid; With 1,4-diaza-bicyclo[2.2.2]octane; rose bengal; acetic acid; In acetonitrile; at 20 ℃; for 2h; Flow reactor; Irradiation;

With sulfuric acid; In methanol; water; at 20 ℃; for 12h;

DOI:10.1002/adsc.201601108

Reference yield: 93.3%

4-Bromobenzoic acid (586-76-5) + methylamine (74-89-5) → N-methyl-p-aminobenzoic acid (10541-83-0,937737-33-2)

Guidance literature:

With copper; In water; at 100 ℃; for 12h;

DOI:10.1021/jo102169t

Reference yield: 91.0%

4-(benzotriazol-1-ylmethyl-amino)-benzoic acid (62001-43-8) → N-methyl-p-aminobenzoic acid (10541-83-0,937737-33-2)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; for 0.333333h; Heating;

upstream raw materials:

4-bromo-N-methylaniline

4-amino-benzoic acid

dimethyl sulfate

methyl iodide

Downstream raw materials:

4-methylamino-benzoic acid-(2-piperidino-ethyl ester)

4-(formyl-methyl-amino)-benzoic acid

10-methyl-pteroic acid

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid

Refernces

• 1、 Kim, Youseung,Maciag, Anna E.,Cao, Zhao,Deschamps, Jeffrey R.,Saavedra, Joseph E.,Keefer, Larry K.,Holland, Ryan J.. "PABA/NO lead optimization: Improved targeting of cytotoxicity to glutathione S-transferase P1-overexpressing cancer cells". . p. 4980 - 4988. Retrieved 2015.
• 2、 Jiao, Jiao,Zhang, Xi-Ru,Chang, Ning-Hui,Wang, Jie,Wei, Jun-Fa,Shi, Xian-Ying,Chen, Zhan-Guo. "A facile and practical copper powder-catalyzed, organic solvent-and ligand-free ullmann amination of aryl halides". supporting information; experimental part. p. 1180 - 1183. Retrieved 2011/04/24.