Coumarin 314

Base Information

• Chemical Name: Coumarin 314
• CAS No.: 55804-66-5
• Deprecated CAS: 75496-02-5
• Molecular Formula: C18H19 N O4
• Molecular Weight: 313.353
• Hs Code.: 29322985
• European Community (EC) Number: 259-825-1
• NSC Number: 338967
• UNII: WM5MO60RUO
• DSSTox Substance ID: DTXSID4069052
• Nikkaji Number: J227.847B
• Wikidata: Q27123014
• ChEMBL ID: CHEMBL2000369
• Mol file: 55804-66-5.mol

Synonyms:coumarin 314

Chemical Property of Coumarin 314

Chemical Property:

• Vapor Pressure: 7.83E-12mmHg at 25°C
• Melting Point: 140-144 °C(lit.)
• Refractive Index: 1.63
• Boiling Point: 542.5 °C at 760 mmHg
• PKA: 5.37±0.40(Predicted)
• Flash Point: 281.9 °C
• PSA: 59.75000
• Density: 1.33g/cm³
• LogP: 2.73350
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 543

Purity/Quality:

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

Coumarin 314 ^*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:

• Chemical Classes: Dyes -> Coumarin Dyes
• Canonical SMILES: CCOC(=O)C1=CC2=CC3=C4C(=C2OC1=O)CCCN4CCC3
• Uses: Coumarin 314 is a laser dye used for research purposes.Dyes and metabolites.

Technology Process of Coumarin 314

There total 2 articles about Coumarin 314 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: 79.2%

9-formyl-8-hydroxyjulolidine (63149-33-7) + diethyl malonate (105-53-3) → ethyl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f ]-pyrido[3,2,1-ij]quinoline-10-carboxylate (55804-66-5)

Guidance literature:

With piperidine; In ethanol; for 6h; Reflux;

DOI:10.1039/c4cc04192e

Reference yield:

8-hydroxyjulolidine (41175-50-2) → ethyl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f ]-pyrido[3,2,1-ij]quinoline-10-carboxylate (55804-66-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / POCl₃

2: 42 percent / piperidine / butan-1-ol; acetic acid

With piperidine; trichlorophosphate; In acetic acid; butan-1-ol; 1: Vilsmeier reaction / 2: Knoevenagel condensation;

DOI:10.1080/00304940109356622

Reference yield: 85.0%

ethyl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f ]-pyrido[3,2,1-ij]quinoline-10-carboxylate (55804-66-5) → coumarin-343 (55804-65-4)

Guidance literature:

With hydrogenchloride; water; at 25 ℃; for 24h;

DOI:10.1016/j.dyepig.2018.12.064

upstream raw materials:

9-formyl-8-hydroxyjulolidine

diethyl malonate

8-hydroxyjulolidine

Downstream raw materials:

coumarin-6H

11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbaldehyde

coumarin-343

Refernces

• 1、 Ismail, Ismail,Wang, Dawei,Wang, Zhenghua,Wang, Dan,Zhang, Changyu,Yi, Long,Xi, Zhen. "A julolidine-fused coumarin-NBD dyad for highly selective and sensitive detection of H2S in biological samples". . p. 700 - 706. Retrieved 2019/01/05.
• 2、 Aliaga, Margarita E.,García-Río, Luis,Pessêgo, Márcia,Montecinos, Rodrigo,Fuentealba, Denis,Uribe, Iván,Martín-Pastor, Manuel,García-Beltrán, Olimpo. "Host-guest interaction of coumarin-derivative dyes and cucurbit[7]uril: Leading to the formation of supramolecular ternary complexes with mercuric ions". supporting information. p. 3084 - 3092. Retrieved 2015/04/22.