1-chloro-9-oxo-10H-acridine-4-carboxylic Acid

Base Information

• Chemical Name: 1-chloro-9-oxo-10H-acridine-4-carboxylic Acid
• CAS No.: 80258-99-7
• Molecular Formula: C₁₄H₈ClNO₃
• Molecular Weight: 273.675
• DSSTox Substance ID: DTXSID40408006
• Wikidata: Q82213363
• ChEMBL ID: CHEMBL5169618
• Mol file: 80258-99-7.mol

Synonyms:80258-99-7;1-chloro-9-oxo-10H-acridine-4-carboxylic Acid;1-CHLORO-9,10-DIHYDRO-9-OXO-4-ACRIDINECARBOXYLIC ACID;SCHEMBL8121610;CHEMBL5169618;DTXSID40408006;1-CHLORO-9,10-DIHYDRO-9-OXO-4-ACRIDINECARBOXYLICACID;AG-H-22384;1-CHLORO-9-OXO-9,10-DIHYDROACRIDINE-4-CARBOXYLIC ACID

Chemical Property of 1-chloro-9-oxo-10H-acridine-4-carboxylic Acid

Chemical Property:

• Vapor Pressure: 8.6E-11mmHg at 25°C
• Boiling Point: 499.4°C at 760 mmHg
• Flash Point: 255.8°C
• PSA: 70.16000
• Density: 1.494g/cm³
• LogP: 3.03290
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 273.0192708
• Heavy Atom Count: 19
• Complexity: 400

Purity/Quality:

98% ^*data from raw suppliers

1-CHLORO-9,10-DIHYDRO-9-OXO-4-ACRIDINECARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C=CC(=C3N2)C(=O)O)Cl

Technology Process of 1-chloro-9-oxo-10H-acridine-4-carboxylic Acid

There total 9 articles about 1-chloro-9-oxo-10H-acridine-4-carboxylic 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: 76.0%

lobenzarit (63329-53-3) → 3-chloro-5-carboxy-9(10H)-acridanone (24782-72-7) + 1-chloro-9-oxo-9,10-dihydroacridine-4-carboxylic acid (80258-99-7)

Guidance literature:

With sulfuric acid; at 100 ℃; for 2h;

DOI:10.1021/jm00365a013

Reference yield: 66.0%

lobenzarit (63329-53-3) → 1-chloro-9-oxo-9,10-dihydroacridine-4-carboxylic acid (80258-99-7)

Guidance literature:

With sulfuric acid; at 100 ℃; for 4h;

DOI:10.1021/jm00345a015

Reference yield:

2,4 dichlorobenzoic acid (50-84-0) → 1-chloro-9-oxo-9,10-dihydroacridine-4-carboxylic acid (80258-99-7)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃, Cu, cuprous oxide / 2-ethoxy-ethanol / 0.5 h / 120 °C

2: 76 percent / conc. H₂SO₄ / 2 h / 100 °C

With copper(I) oxide; sulfuric acid; copper; potassium carbonate; In 2-ethoxy-ethanol;

DOI:10.1021/jm00365a013

upstream raw materials:

lobenzarit

2-amino-4-chloro-benzoic acid methyl ester

2,4 dichlorobenzoic acid

Diphenyliodonium-2-carboxylate

Downstream raw materials:

1-Chloro-acridine-4-carboxylic acid (2-dimethylamino-ethyl)-amide

Refernces

• 1、 Zhang, Bin,Chen, Kang,Wang, Ning,Gao, Chunmei,Sun, Qinsheng,Li, Lulu,Chen, Yuzong,Tan, Chunyan,Liu, Hongxia,Jiang, Yuyang. "Molecular design, synthesis and biological research of novel pyridyl acridones as potent DNA-binding and apoptosis-inducing agents". supporting information. p. 214 - 226. Retrieved 2015/03/04.
• 2、 Rewcastle, Gordon W.,Denny, William A.. "The Synthesis of Substituted 9-Oxoacridan-4-carboxylic Acids; Part 3. The Reaction of Methyl Anthranilates with Diphenyliodonium-2-carboxylates". . p. 220 - 222. Retrieved 2007/10/02.