Coumarin 337

Base Information

• Chemical Name: Coumarin 337
• CAS No.: 55804-68-7
• Molecular Formula: C₁₆H₁₄N₂O₂
• Molecular Weight: 266.299
• Hs Code.: 29322985
• European Community (EC) Number: 259-827-2
• NSC Number: 338968
• UNII: 7PZP222LOZ
• DSSTox Substance ID: DTXSID4069054
• Nikkaji Number: J296.503H
• ChEMBL ID: CHEMBL1998632
• Mol file: 55804-68-7.mol

Synonyms:Coumarin 337;55804-68-7;Coumarin 523;7PZP222LOZ;EINECS 259-827-2;NSC338968;2,3,6,7-Tetrahydro-11-oxo-1H,5H,11H-(1)benzopyrano(6,7,8-ij)quinolizine-10-carbonitrile;NSC 338968;NSC-338968;1H,5H,11H-(1)Benzopyrano(6,7,8-ij)quinolizine-10-carbonitrile, 2,3,6,7-tetrahydro-11-oxo-;1H,5H,11H-[1]Benzopyrano[6,7,8-ij]quinolizine-10-carbonitrile, 2,3,6,7-tetrahydro-11-oxo-;4-oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraene-5-carbonitrile;2,3,6,7-Tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carbonitrile;11-Oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbonitrile;UNII-7PZP222LOZ;quinolizine-10-carbonitrile;SCHEMBL2844010;CHEMBL1998632;DTXSID4069054;MFCD00051332;AKOS000813906;AS-56413;NCI60_002993;C3063;CS-0358073;D89539;2,3,6,7-Tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij];10-CYANO-1,2,5,6-TETRAHYDRO-3H,7H,11H-(1)BENZOPYRANO(6,7,8-IJ)QUINOLIZIN-11-ONE;1H,11H-[1]Benzopyrano[6,7,8-ij]quinolizine-10-carbonitrile, 2,3,6,7-tetrahydro-11-oxo-;(2,3,6,7-tetrahydro-11-oxo-1H,5H,11H-[1]-benzopyrano[6,7,8-ij]quinolizine-10-carbonitrile);4-oxo-3-oxa-13-azatetracyclo[7.7.1.0?,?.0??,??]heptadeca-1,5,7,9(17)-tetraene-5-carbonitrile

Chemical Property of Coumarin 337

Chemical Property:

• Appearance/Colour: orange needle-like crystals
• Vapor Pressure: 6.46E-12mmHg at 25°C
• Melting Point: 250 °C (dec.)(lit.)
• Refractive Index: 1.674
• Boiling Point: 544.5 °C at 760 mmHg
• PKA: 5.14±0.40(Predicted)
• Flash Point: 283.1 °C
• PSA: 57.24000
• Density: 1.38 g/cm³
• LogP: 2.42848
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 266.105527694
• Heavy Atom Count: 20
• Complexity: 518

Purity/Quality:

99% ^*data from raw suppliers

Coumarin 337 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C3C(=C4C(=C2)C=C(C(=O)O4)C#N)CCCN3C1
• Uses: Coumarin 337 is used as a laser dye.

Technology Process of Coumarin 337

There total 4 articles about Coumarin 337 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: 62.0%

9-formyl-8-hydroxyjulolidine (63149-33-7) + N,N-dimethylcyanoacetamide (7391-40-4) → coumarin 337 (55804-68-7)

Guidance literature:

With piperidine; In ethanol; at 70 ℃; for 4h;

DOI:10.1016/j.tet.2019.130538

Reference yield: 27.0%

C24H23N5O6 → coumarin 337 (55804-68-7)

Guidance literature:

With cetyltrimethylammonim bromide; thiophenol; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; In acetonitrile; at 20 ℃; for 1h; pH=7.4;

DOI:10.1016/j.tet.2019.130538

Reference yield:

9-formyl-8-hydroxyjulolidine (63149-33-7) → coumarin 337 (55804-68-7)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / 4 h / 70 °C

2: piperidine / ethanol / 4 h / 70 °C

3: thiophenol; cetyltrimethylammonim bromide; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid / acetonitrile / 1 h / 20 °C / pH 7.4

With piperidine; cetyltrimethylammonim bromide; potassium carbonate; thiophenol; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; In ethanol; acetone; acetonitrile;

DOI:10.1016/j.tet.2019.130538

upstream raw materials:

9-formyl-8-hydroxyjulolidine

N,N-dimethylcyanoacetamide

ethyl 2-cyanoacetate

Refernces

• 1、 Deiana, Marco,Obi, Ikenna,Andreasson, M?ns,Tamilselvi, Shanmugam,Chand, Karam,Chorell, Erik,Sabouri, Nasim. "A Minimalistic Coumarin Turn-On Probe for Selective Recognition of Parallel G-Quadruplex DNA Structures". . p. 1365 - 1376. Retrieved 2021/08/25.