7-Diethylamino-4-methylcoumarin

Base Information

• Chemical Name: 7-Diethylamino-4-methylcoumarin
• CAS No.: 91-44-1
• Deprecated CAS: 11118-21-1,70726-42-0,71123-71-2,73201-22-6,96538-19-1,61968-71-6,12224-03-2,129038-92-2,52232-20-9,58694-55-6,86090-68-8,12651-35-3,74029-28-0,1215069-65-0,2252489-56-6,1215069-65-0,12651-35-3,129038-92-2,52232-20-9,58694-55-6,61968-71-6,70726-42-0,71123-71-2,73201-22-6,74029-28-0,86090-68-8,96538-19-1
• Molecular Formula: C14H17NO2
• Molecular Weight: 231.294
• Hs Code.: 29322090
• European Community (EC) Number: 202-068-9,612-902-7
• NSC Number: 61830
• UNII: 1SFJ7F6R2C
• DSSTox Substance ID: DTXSID9025035
• Nikkaji Number: J48.490C
• Wikidata: Q27123009
• Pharos Ligand ID: 1T7CBMUDVQZA
• ChEMBL ID: CHEMBL315348
• Mol file: 91-44-1.mol

Synonyms:4-methyl-7-diethylaminocoumarin

Chemical Property of 7-Diethylamino-4-methylcoumarin

Chemical Property:

• Appearance/Colour: light tan powder
• Vapor Pressure: 0-0.003Pa at 20-25℃
• Melting Point: 72-75 °C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 391.7 °C at 760 mmHg
• PKA: 3.51±0.20(Predicted)
• Flash Point: 152 °C
• PSA: 33.45000
• Density: 1.122 g/cm³
• LogP: 2.94760
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: slightly soluble
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 231.125928785
• Heavy Atom Count: 17
• Complexity: 320

Purity/Quality:

99%min ^*data from raw suppliers

Coumarin1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Coumarin Dyes
• Canonical SMILES: CCN(CC)C1=CC2=C(C=C1)C(=CC(=O)O2)C
• Uses: Optical bleach in textile industry, in coatings for paper, labels, book covers, etc.; to lighten plastics, resins, varnishes, and lacquers; invisible marking agent. 7-(Diethylamino)-4-methylcoumarin, is potentially useful as a laser dye.

Technology Process of 7-Diethylamino-4-methylcoumarin

There total 36 articles about 7-Diethylamino-4-methylcoumarin 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: 95.0%

ethyl acetoacetate (141-97-9) + 3-diethylaminophenol (91-68-9) → 7-diethylamino-4-methylcoumarin (91-44-1,61968-71-6)

Guidance literature:

With acetic anhydride; ammonium chloride; zinc; at 127 - 135 ℃; Reagent/catalyst; Temperature; Inert atmosphere; Large scale;

Reference yield: 85.0%

C14H17NO2 → 7-diethylamino-4-methylcoumarin (91-44-1,61968-71-6) + C14H17NO2

Guidance literature:

With C₅₅H₉₂AuClN₂O₂₈; In water; at 37 ℃; for 42h; Reagent/catalyst; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.202001990

Reference yield: 43.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 7-(diethylamino)-3-iodo-4-methyl-2H-chromen-2-one (107995-74-4) → 7-diethylamino-4-methylcoumarin (91-44-1,61968-71-6) + 7-Diethylamino-4-methyl-3-((E)-styryl)-chromen-2-one (132093-41-5)

Guidance literature:

for 10h; Further byproducts given; Irradiation;

DOI:10.1007/BF00480857

upstream raw materials:

ethyl acetoacetate

3-diethylaminophenol

furan

7-(diethylamino)-3-iodo-4-methyl-2H-chromen-2-one

Downstream raw materials:

N-phenylimide of 2-oxo-4,8-dimethyl-7-ethyl-7,8,9,10-tetrahydro-2H-pyrano<3,2-h>quinoline-9,c-10-dicarboxylic acid

3-(1-phenylethyl)-4-methyl-7-aminocoumarin

6-(1-phenylethyl)-4-methyl-7-aminocoumarin

4-Methyl-7-diethylamino-2-(5,5-dimethylcyclohexa-1,3-dione-2-ilidene)-2H-1-benzopiran

Refernces

• 1、 Fan, Hongli,Wang, Lingqiang,Wang, Xiaolong. "Synthesis and fluorescent properties of coumarin-benzimidazole and coumarin–phenanthroimidazole hybrids". . p. 9 - 13. Retrieved 2019/11/13.
• 2、 Zhu, Xiaolei,Xu, Guangcan,Chamoreau, Lise-Marie,Zhang, Yongmin,Mouriès-Mansuy, Virginie,Fensterbank, Louis,Bistri-Aslanoff, Olivia,Roland, Sylvain,Sollogoub, Matthieu. "Permethylated NHC-Capped α- and β-Cyclodextrins (ICyDMe) Regioselective and Enantioselective Gold-Catalysis in Pure Water". supporting information. p. 15901 - 15909. Retrieved 2020/10/12.