4-Carboxy-9-acridanone

Base Information

• Chemical Name: 4-Carboxy-9-acridanone
• CAS No.: 24782-64-7
• Molecular Formula: C14H9 N O3
• Molecular Weight: 239.23
• Hs Code.: 2933990090
• European Community (EC) Number: 622-408-3
• DSSTox Substance ID: DTXSID00393641
• Nikkaji Number: J1.321.173F
• Wikidata: Q82192471
• ChEMBL ID: CHEMBL541514
• Mol file: 24782-64-7.mol

Synonyms:4-Carboxy-9-acridanone;24782-64-7;9-oxo-9,10-dihydroacridine-4-carboxylic acid;9-oxo-10H-acridine-4-carboxylic Acid;acridone-4-carboxylic acid;9,10-dihydro-9-oxoacridine-4-carboxylic acid;4-Acridinecarboxylic acid, 9,10-dihydro-9-oxo-;4-carboxyacridone;4-carboxyacridanone;MFCD00957937;CHEMBL541514;SCHEMBL4943278;SCHEMBL21119051;DTXSID00393641;BATAOFZEDHPRTM-UHFFFAOYSA-N;AKOS002664589;AS-67219;HY-34887;CS-0029726;9-oxo-9,10-dihydroacridine-4-carboxylicacid;9,10-dihydro-9-oxo-4-acridinecarboxylic acid;EN300-183303;A924853;J-015672;Z1873903872

Chemical Property of 4-Carboxy-9-acridanone

Chemical Property:

• Vapor Pressure: 1.24E-09mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.673
• Boiling Point: 469.9°C at 760 mmHg
• PKA: 3.13±0.20(Predicted)
• Flash Point: 238°C
• PSA: 70.16000
• Density: 1.397g/cm³
• LogP: 2.37950
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 239.058243149
• Heavy Atom Count: 18
• Complexity: 368

Purity/Quality:

98% ^*data from raw suppliers

4-Carboxy-9-acridanone(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(N2)C(=CC=C3)C(=O)O
• Uses: 4-Carboxy-9-acridanone is a useful stain/dye for biochemical research.

Technology Process of 4-Carboxy-9-acridanone

There total 2 articles about 4-Carboxy-9-acridanone 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: 47.0%

Vanadox (579-92-0) + trifluoroacetic anhydride (407-25-0) → 9-Oxoacridan-4-carboxylic acid (24782-64-7) + 2,2'-(trifluoroacetylimino)bis-benzoic acid

Guidance literature:

In acetonitrile; for 0.166667h; Heating;

DOI:10.1039/b306032b

Reference yield:

2-aminoisophthalic acid (39622-79-2) → 9-Oxoacridan-4-carboxylic acid (24782-64-7)

Guidance literature:

Multi-step reaction with 3 steps

2: 84 percent / N-ethylmorpholine / CuCl / benzene; various solvent(s) / 1 h / Heating

3: 96 percent / polyphosphoric acid / 2 h / 120 °C

With N-ethylmorpholine;; PPA; copper(l) chloride; In benzene;

DOI:10.1055/s-1985-31164

Reference yield: 78.0%

9-Oxoacridan-4-carboxylic acid (24782-64-7) + L-tyrosine methyl ester HCl (3417-91-2) → methyl 3-(4-hydroxyphenyl)-2-(9-oxo-9,10-dihydroacridine-4-carboxamido)propanoate

Guidance literature:

With chloroformic acid ethyl ester; triethylamine; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1039/c4ob02666g

upstream raw materials:

Vanadox

trifluoroacetic anhydride

2-aminoisophthalic acid

Downstream raw materials:

acridine-4-carboxylic acid

7-nitro-9,10-dihydro-9-oxo-4-acridine carboxylic acid

p-nitrophenyl acridone-4-carboxylate

N-<2-(dimethylamino)ethyl>-9,10-dihydro-9-oxo-4-acridinecarboxamide

Refernces

• 1、 Rewcastle, Gordon W.,Denny, William A.. "The Synthesis of Substituted 9-Oxoacridan-4-carboxylic Acids; Part 2. The Use of 2-Iodoisophthalic Acid in the Jourdan-Ullmann Reaction". . p. 217 - 220. Retrieved 2007/10/02.