7-Hydroxy-4-methylcoumarin diethylphosphate

Base Information

• Chemical Name: 7-Hydroxy-4-methylcoumarin diethylphosphate
• CAS No.: 897-83-6
• Molecular Formula: C₁₄H₁₇O₆P
• Molecular Weight: 312.259
• European Community (EC) Number: 635-884-2
• DSSTox Substance ID: DTXSID301008943
• Nikkaji Number: J48.494F
• Wikidata: Q83005576
• Mol file: 897-83-6.mol

Synonyms:7-Hydroxy-4-methylcoumarin diethylphosphate;diethyl (4-methyl-2-oxochromen-7-yl) phosphate;COUMARIN, 7-HYDROXY-4-METHYL-, DIETHYLPHOSPHATE;SCHEMBL20710799;DTXSID301008943;NCGC00485276-01;LS-55223;Diethyl 4-methyl-2-oxo-2H-1-benzopyran-7-yl phosphate;Phosphoric acid=diethyl=4-methyl-2-oxo-2H-1-benzopyran-7-yl ester

Chemical Property of 7-Hydroxy-4-methylcoumarin diethylphosphate

Chemical Property:

• Vapor Pressure: 6.98E-07mmHg at 25°C
• Boiling Point: 408.5°C at 760 mmHg
• Flash Point: 214.3°C
• PSA: 84.78000
• Density: 1.272g/cm³
• LogP: 3.35290
• Storage Temp.: −20°C
• Solubility.: DMSO: 5 mg/mL
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 312.07627526
• Heavy Atom Count: 21
• Complexity: 450

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diethylumbelliferyl phosphate ≥98% (HPLC), oil ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOP(=O)(OCC)OC1=CC2=C(C=C1)C(=CC(=O)O2)C
• Uses: Diethylumbelliferyl phosphate has been used as a lipase inhibitor to treat wild-type myeloblasts for in vitro neutrophil differentiation assays.

Technology Process of 7-Hydroxy-4-methylcoumarin diethylphosphate

There total 5 articles about 7-Hydroxy-4-methylcoumarin diethylphosphate 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: 89.0%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + triethyl phosphate (78-40-0) → O,O-diethyl-O-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-phosphate (897-83-6)

Guidance literature:

triethyl phosphate; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 20 ℃; for 0.166667h;

7-hydroxy-4-methyl-chromen-2-one; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/acs.orglett.8b02073

Reference yield: 60.5%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + phosphonic acid diethyl ester (762-04-9) → O,O-diethyl-O-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-phosphate (897-83-6)

Guidance literature:

With triethylamine; In tetrachloromethane; acetone; at 0 - 20 ℃; for 8.5h;

DOI:10.1039/c9nj04787e

Reference yield: 40.0%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + diethyl chlorophosphate (814-49-3) → O,O-diethyl-O-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-phosphate (897-83-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 5 ℃; for 12h;

DOI:10.1016/j.jfluchem.2006.07.017

upstream raw materials:

potasan

7-hydroxy-4-methyl-chromen-2-one

diethyl chlorophosphate

triethyl phosphate

Refernces

• 1、 Huang, Hai,Ash, Jeffrey,Kang, Jun Yong. "Tf2O-Promoted Activating Strategy of Phosphate Analogues: Synthesis of Mixed Phosphates and Phosphinate". supporting information. p. 4938 - 4941. Retrieved 2018/08/24.
• 2、 Abdou, Wafaa M.,Mahran, M. Refat,Sidky, Mahmoud M.,Wamhoff, Heinrich. "PHOTOCHEMISTRY OF PESTICIDES, 13. SOME PHOTOREACTIONS OF O,O-DIETHYL-O-(4-METHYL-2-OXO-2H-1-BENZOPYRAN-7-YL)-PHOSPHOROTHIOATE (POTASAN)". . p. 199 - 204. Retrieved 2007/10/02.