Xanthene-9-carboxylic acid

Base Information

• Chemical Name: Xanthene-9-carboxylic acid
• CAS No.: 82-07-5
• Molecular Formula: C14H10O3
• Molecular Weight: 226.232
• Hs Code.: 29329990
• European Community (EC) Number: 201-394-9
• NSC Number: 66208
• UNII: 63A81F6A8V
• DSSTox Substance ID: DTXSID70231501
• Nikkaji Number: J40.679A
• Wikidata: Q27263597
• ChEMBL ID: CHEMBL520
• Mol file: 82-07-5.mol

Synonyms:xanthene-9-carboxylic acid;xanthenecarboxylic acid

Chemical Property of Xanthene-9-carboxylic acid

Chemical Property:

• Vapor Pressure: 7.99E-07mmHg at 25°C
• Melting Point: 221-225 °C(lit.)
• Boiling Point: 391.3 °C at 760 mmHg
• PKA: 4.30±0.20(Predicted)
• Flash Point: 153.1 °C
• PSA: 46.53000
• Density: 1.335 g/cm³
• LogP: 3.00880
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: Insoluble in water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 226.062994177
• Heavy Atom Count: 17
• Complexity: 280

Purity/Quality:

99% ^*data from raw suppliers

Xanthene-9-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C3O2)C(=O)O
• Uses: Xanthene-9-carboxylic Acid is xanthrene derivative that is capable of inhibiting the TTR conformational changes facilitating amyloid fibril formation. Transesterification of the ethyl ester of commercially available xanthene-9-carboxylic acid yeildits 3- quinuclidinyl ester.

Technology Process of Xanthene-9-carboxylic acid

There total 15 articles about Xanthene-9-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: 95.3%

9H-Xanthene-9-carbonitrile (85554-24-1) → xanthene-9-carboxylic acid (82-07-5)

Guidance literature:

With sodium hydroxide; In water; at 100 ℃; for 8h; Concentration; Temperature;

Reference yield: 76.0%

xanthene (92-83-1) + carbon dioxide (124-38-9,18923-20-1) → xanthene-9-carboxylic acid (82-07-5)

Guidance literature:

xanthene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;

carbon dioxide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.333333h;

DOI:10.1002/ejoc.202100913

Reference yield: 73.0%

C15H13NO3 → xanthene-9-carboxylic acid (82-07-5)

Guidance literature:

With tert.-butylnitrite; water; at 29 ℃; for 0.583333h;

DOI:10.1021/acs.joc.7b00570

upstream raw materials:

xanthene

carbon dioxide

tert.-butyl lithium

9H-xanthene-9-carbonyl chloride

Downstream raw materials:

9H-xanthene-9-carboxylic acid methyl ester

xanthene-9-carboxylic acid ethyl ester

N,N-diethylaminoethyl xanthene-9-carboxylate

xanthene-9-carboxylic acid-(2-diisopropylamino-ethyl ester)

Refernces

• 1、 Yedage, Subhash L.,Bhanage, Bhalchandra M.. "Tert-Butyl Nitrite-Mediated Synthesis of N-Nitrosoamides, Carboxylic Acids, Benzocoumarins, and Isocoumarins from Amides". . p. 5769 - 5781. Retrieved 2017/06/07.
• 2、 Potter, Garrett T.,Jayson, Gordon C.,Miller, Gavin J.,Gardiner, John M.. "Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids". supporting information. p. 5153 - 5156. Retrieved 2015/08/19.