4,4'-(Ethylenediimino)dibenzoic acid

Base Information

• Chemical Name: 4,4'-(Ethylenediimino)dibenzoic acid
• CAS No.: 95627-01-3
• Molecular Formula: C16H16N2O4
• Molecular Weight: 300.30924
• DSSTox Substance ID: DTXSID60700731
• Wikidata: Q82632186
• Mol file: 95627-01-3.mol

Synonyms:4,4'-(ETHYLENEDIIMINO)DIBENZOIC ACID;95627-01-3;4-[2-(4-carboxyanilino)ethylamino]benzoic acid;DTXSID60700731;FT-0668263;4,4'-(1,2-Ethanediyldiimino)bisbenzoic Acid;4,4'-(Ethane-1,2-diyldiazanediyl)dibenzoic acid;4,4/'-(Ethane-1,2-diyldiazanediyl)dibenzoic acid;4,4 inverted exclamation mark -(Ethylenediimino)dibenzoic Acid

Chemical Property of 4,4'-(Ethylenediimino)dibenzoic acid

Chemical Property:

• PSA: 98.66000
• LogP: 2.75300
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 300.11100700
• Heavy Atom Count: 22
• Complexity: 336

Purity/Quality:

97% ^*data from raw suppliers

4,4’-(Ethylenediimino)dibenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)O)NCCNC2=CC=C(C=C2)C(=O)O
• Uses: A N,N'-diarylethylenediamine derivative as models of tetrahydrofolic acid in nonenzymic reactions. A N,N''-diarylethylenediamine derivative as models of tetrahydrofolic acid in nonenzymic reactions.

Technology Process of 4,4'-(Ethylenediimino)dibenzoic acid

There total 7 articles about 4,4'-(Ethylenediimino)dibenzoic 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: 94.4%

C19H20N2O5 → N,N'-bis(4-carboxyphenyl)ethylenediamine (95627-01-3)

Guidance literature:

With water; sodium hydroxide; In methanol; at 100 ℃; for 24h;

DOI:10.1021/acs.joc.8b00151

Reference yield:

4-methoxycarbonyl aniline (619-45-4) → N,N'-bis(4-carboxyphenyl)ethylenediamine (95627-01-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Na₂CO₃ / 140 °C

2: aqueous KOH

With potassium hydroxide; sodium carbonate;

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → N,N'-bis(4-carboxyphenyl)ethylenediamine (95627-01-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sulfuric acid / methanol / 20 h / 100 °C

2.1: orthoformic acid triethyl ester / 12 h / 140 °C

2.2: 24 h / 140 °C

3.1: potassium carbonate / acetonitrile / 100 °C

4.1: sodium hydroxide; water / methanol / 24 h / 100 °C

With sulfuric acid; water; potassium carbonate; orthoformic acid triethyl ester; sodium hydroxide; In methanol; acetonitrile;

DOI:10.1021/acs.joc.8b00151

upstream raw materials:

4,4'-ethane-1,2-diyldiamino-bis-benzoic acid dimethyl ester

ethylene dibromide

4-methoxycarbonyl aniline

methyl 4-{[4-(methoxycarbonyl)phenyl]-amino}methyleneaminobenzoate

Downstream raw materials:

4,4'-imidazolidine-1,3-diyl-di-benzoic acid

1,3-bis-(4-carboxy-phenyl)-4,5-dihydro-imidazolium; chloride

Refernces