2-(Phenylamino)terephthalic acid

Base Information

• Chemical Name: 2-(Phenylamino)terephthalic acid
• CAS No.: 566155-75-7
• Molecular Formula: C14H11NO4
• Molecular Weight: 257.246
• DSSTox Substance ID: DTXSID30466236
• Mol file: 566155-75-7.mol

Synonyms:2-(phenylamino)terephthalic acid;566155-75-7;2-anilinoterephthalic Acid;2-PHENYLAMINO-TEREPHTHALIC ACID;5-phenylamino-terephthalic Acid;2-(phenylamino)terephthalicacid;SCHEMBL2476797;YSZC2761;DTXSID30466236;NGZJULVKWHXKMF-UHFFFAOYSA-N;AKOS015965854;2-(phenylamino)benzene-1,4-dioic acid;BP-21081

Chemical Property of 2-(Phenylamino)terephthalic acid

Chemical Property:

• PSA: 86.63000
• LogP: 2.89960
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 257.06880783
• Heavy Atom Count: 19
• Complexity: 338

Purity/Quality:

90% ^*data from raw suppliers

2-(Phenylamino)benzene-1,4-dioic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC2=C(C=CC(=C2)C(=O)O)C(=O)O

Technology Process of 2-(Phenylamino)terephthalic acid

There total 11 articles about 2-(Phenylamino)terephthalic 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: 99.3%

5-phenylamino-terephthalic acid dimethyl ester (566155-74-6) → 2-(phenylamino)terephthalic acid (566155-75-7)

Guidance literature:

With lithium hydroxide monohydrate; In ethanol; at 20 ℃;

Reference yield: 90.0%

2-bromo-1,4-benzenedicarboxylic acid (586-35-6) + aniline (62-53-3) → 2-(phenylamino)terephthalic acid (566155-75-7)

Guidance literature:

With copper(I) bromide; In toluene; at 120 ℃; for 0.5h;

DOI:10.1039/b400734b

Reference yield:

dimethyl 2-bromoterephthalate (18643-86-2) → 2-(phenylamino)terephthalic acid (566155-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / cesium carbonate / palladium(II) acetate; (S)-(-)-2,2'-bis(diphenylphosphino)-1,1,-binaphthyl / toluene / 24 h / 100 °C

2: 96 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 0.5 h / Heating

With lithium hydroxide; caesium carbonate; palladium diacetate; In tetrahydrofuran; methanol; water; toluene; 1: Buchwald-Hartwig coupling;

DOI:10.1021/jm070299x

upstream raw materials:

2-bromo-1,4-benzenedicarboxylic acid

aniline

5-phenylamino-terephthalic acid dimethyl ester

dimethyl 2-bromoterephthalate

Downstream raw materials:

4-(4-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)piperidine-1-carbonyl)-2-(phenylamino)benzoic acid trifluoroacetic acid

4-((2-ethylisoindolin-5-yl)carbamoyl)-2-(phenylamino)benzoic acid trifluoroacetic acid

4-((2-ethylisoindolin-5-yl)carbamoyl)-2-(phenylamino)benzoic acid trifluoroacetic acid

(2-(phenylamino)-1,4-phenylene)bis((4-(pyrrolidin-1-yl)piperidin-1-yl)methanone)

Refernces

• 1、 Bretonniere, Yann,Cann, Martin J,Parker, David,Slater, Rachel. "Design, synthesis and evaluation of ratiometric probes for hydrogencarbonate based on europium emission.". . p. 1624 - 1632. Retrieved 2004.
• 2、 Benoit, Adam R.,Schiaffo, Charles,Salomon, Christine E.,Goodell, John R.,Hiasa, Hiroshi,Ferguson, David M.. "Synthesis and evaluation of N-alkyl-9-aminoacridines with antibacterial activity". supporting information. p. 3014 - 3017. Retrieved 2014/06/24.
• 3、 Howell, Lesley A.,Howman, Aaron,O'Connell, Maria A.,Mueller, Anja,Searcey, Mark. "Synthesis and evaluation of 9-aminoacridines derived from benzyne click chemistry". scheme or table. p. 5880 - 5883. Retrieved 2010/06/15.