2H-1-Benzopyran-2-one, 7-(diethylamino)-

Base Information

• Chemical Name: 2H-1-Benzopyran-2-one, 7-(diethylamino)-
• CAS No.: 20571-42-0
• Deprecated CAS: 71123-92-7
• Molecular Formula: C13H15NO2
• Molecular Weight: 217.268
• Hs Code.: 2932209090
• European Community (EC) Number: 243-888-7
• UNII: 8NX73KU7CZ
• DSSTox Substance ID: DTXSID9066627
• Nikkaji Number: J280.622C
• Wikidata: Q27208916
• Metabolomics Workbench ID: 74221
• ChEMBL ID: CHEMBL1430816
• Mol file: 20571-42-0.mol

Synonyms:20571-42-0;7-Diethylaminocoumarin;7-(Diethylamino)coumarin;2H-1-Benzopyran-2-one, 7-(diethylamino)-;7-(diethylamino)chromen-2-one;7-(Diethylamino)-2H-chromen-2-one;Coumarin 466;Coumarine, 7-diethylamino-;7-(Diethylamino)-2H-1-benzopyran-2-one;7-(Diethylamino)-2-benzopyrone;CHEMBL1430816;EINECS 243-888-7;Coumarin 110;7-(Diethylamino);7-diethylamino-coumarin;7-Diethylamino coumarin;Coumarin, 7-diethylamino-;8NX73KU7CZ;Oprea1_055827;Oprea1_235891;MLS000712013;Coumarin, 7-(diethylamino)-;SCHEMBL142022;DTXSID9066627;CHEBI:120776;HMS1675D07;HMS2633O15;HMS3363H02;BDBM50242749;MFCD00232946;STK331476;7-(diethylamino)-1-benzopyran-2-one;AKOS000668887;AM84710;7-(Diethylamino)-2H-chromen-2-one #;NCGC00245039-01;AS-64513;SMR000281780;CS-0127754;D3354;T70542;A913152;SR-01000313040;J-013427;SR-01000313040-1;Q27208916;Coumarin 466, BioReagent, suitable for fluorescence, >=98.0% (HPLC);EJO

Chemical Property of 2H-1-Benzopyran-2-one, 7-(diethylamino)-

Chemical Property:

• Vapor Pressure: 4.17E-06mmHg at 25°C
• Melting Point: 87.0 to 91.0 °C
• Boiling Point: 384.2°C at 760 mmHg
• PKA: 3.40±0.20(Predicted)
• Flash Point: 154.6°C
• PSA: 33.45000
• Density: 1.155g/cm³
• LogP: 2.63920
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 217.110278721
• Heavy Atom Count: 16
• Complexity: 284

Purity/Quality:

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

Coumarin 466 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 3609055
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Coumarin Dyes
• Canonical SMILES: CCN(CC)C1=CC2=C(C=C1)C=CC(=O)O2
• Uses: Coumarin 466 is a useful coumarin derivative suitable for fluorescence

Technology Process of 2H-1-Benzopyran-2-one, 7-(diethylamino)-

There total 39 articles about 2H-1-Benzopyran-2-one, 7-(diethylamino)- 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: 96.0%

(E)-methyl 4’-N,N-diethylamino-2’-hydroxycinnamate (1416708-65-0) → 7-diethylamino-2H-benzopyran-2-one (20571-42-0)

Guidance literature:

With tributylphosphine; In methanol; at 70 ℃; for 20h; Inert atmosphere;

DOI:10.3762/bjoc.8.186

Reference yield: 95.0%

4-(Diethylamino)salicylaldehyde (17754-90-4) + diethyl malonate (105-53-3) → 7-diethylamino-2H-benzopyran-2-one (20571-42-0)

Guidance literature:

4-(Diethylamino)salicylaldehyde; diethyl malonate; With piperidine; In ethanol; for 18h; Reflux;

With hydrogenchloride; acetic acid; at 115 ℃; for 19h;

Reference yield: 94.0%

7-(diethylamino)coumarin-3-carboxylic acid (50995-74-9) → 7-diethylamino-2H-benzopyran-2-one (20571-42-0)

Guidance literature:

With sulfuric acid; for 8h; Heating;

DOI:10.1007/BF00531317

upstream raw materials:

ethyl 7-diethylaminocoumarin-3-carboxylate

7-(diethylamino)-4-carboxy coumarin

7-(diethylamino)-4-chlorocoumarin

7-(diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Downstream raw materials:

(1S,2S,2aR,8bS)-6-Diethylamino-1,2-diphenyl-1,2,2a,8b-tetrahydro-4-oxa-cyclobuta[a]naphthalen-3-one

(1R,2R,2aS,8bR)-6-Diethylamino-2-phenyl-1-((E)-styryl)-1,2,2a,8b-tetrahydro-4-oxa-cyclobuta[a]naphthalen-3-one

3-acetyl-7-diethylaminocoumarin

2-[-6-[7-(diethylamino)-2-oxo-2H-chromen-3-yl]imidazo[2,1-b][1,3,4]thiadiazole-2-[N-(dimethylaminomethino)] sulfonamido]-3-phenyl-1,3-thiazolidin-4-one

Refernces

• 1、 Jadhav, Manoj M.,Vaghasiya, Jayraj V.,Patil, Dinesh S.,Soni, Saurabh S.,Sekar, Nagaiyan. "Structure-efficiency relationship of newly synthesized 4-substituted donor-π-acceptor coumarins for dye-sensitized solar cells". . p. 5267 - 5275. Retrieved 2018.
• 2、 Zhang, Yuandong,Song, Nan,Li, Yuanyuan,Yang, Zhiyu,Chen, Li,Sun, Tingting,Xie, Zhigang. "Comparative study of two near-infrared coumarin-BODIPY dyes for bioimaging and photothermal therapy of cancer". . p. 4717 - 4724. Retrieved 2019.
• 3、 Li, Zhengqian,Zhou, Ying,Yin, Kai,Yu, Zhu,Li, Yan,Ren, Jun. "A new fluorescence "turn-on" type chemosensor for Fe3+ based on naphthalimide and coumarin". . p. 7 - 11. Retrieved 2014.
• 4、 Jana, Palash,Radhakrishna, Mithun,Kanvah, Sriram,Khatua, Saumyakanti. "A "turn-off" red-emitting fluorophore for nanomolar detection of heparin". . p. 13263 - 13270. Retrieved 2018.
• 5、 Dong, Junqiang,Gao, Jianbo,Wang, Yu,Zhang, Wenda. "Design, synthesis and bioactivity evaluation of coumarin-chalcone hybrids as potential anticancer agents". . . Retrieved 2020.
• 6、 Loredo, Axel,Wang, Lushun,Wang, Shichao,Xiao, Han. "Single-atom switching as a general approach to designing colorimetric and fluorogenic probes for mercury ions". . . Retrieved 2021.
• 7、 García-Beltrán, Olimpo,Cassels, Bruce K.,Mena, Natalia,Nu?ez, Marco T.,Ya?ez, Osvaldo,Caballero, Julio. "A coumarinylaldoxime as a specific sensor for Cu2+ and its biological application". . p. 873 - 876. Retrieved 2014.
• 8、 Li, Jun,Cui, Yuanchao,Bi, Chenxi,Feng, Shaoqiong,Yu, Fengzhen,Yuan, En,Xu, Shengzhen,Hu, Zhe,Sun, Qi,Wei, Dengguo,Yoon, Juyoung. "Oligo(ethylene glycol)-Functionalized Ratiometric Fluorescent Probe for the Detection of Hydrazine in Vitro and in Vivo". . p. 7360 - 7365. Retrieved 2019.
• 9、 Kim, Ja Hyung,Kim, Hyun Jung,Kim, Sang Hoon,Lee, Jae Hong,Do, Jung Ho,Kim, Hae-Jo,Lee, Joung Hae,Kim, Jong Seung. "Fluorescent coumarinyldithiane as a selective chemodosimeter for mercury(II) ion in aqueous solution". . p. 5958 - 5961. Retrieved 2009.
• 10、 Paul, Sima,Ghosh, Pritam,Roy, Partha. "A coumarin based fluorescent chemodosimeter for phosgene gas detection instantaneously in solution and the gas phase". . p. 5784 - 5791. Retrieved 2020.