Coumarin 334

Base Information

• Chemical Name: Coumarin 334
• CAS No.: 55804-67-6
• Molecular Formula: C17H17NO3
• Molecular Weight: 283.327
• Hs Code.: 2934999090
• European Community (EC) Number: 259-826-7
• NSC Number: 369287
• UNII: 2773GTW04S
• DSSTox Substance ID: DTXSID9069053
• Nikkaji Number: J296.502J
• Mol file: 55804-67-6.mol

Synonyms:Coumarin 334;55804-67-6;Coumarin334;Coumarin 521;10-Acetyl-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one;2773GTW04S;EINECS 259-826-7;MFCD00051336;NSC369287;NSC 369287;NSC-369287;10-Acetyl-2,3,6,7-tetrahydro-1H,5H,11H-pyrano-[2,3-f]pyrido[3,2,1-ij]quinolin-11-one;1H,5H,11H-(1)Benzopyrano(6,7,8-ij)quinolizin-11-one, 10-acetyl-2,3,6,7-tetrahydro-;1H,5H,11H-[1]Benzopyrano[6,7,8-ij]quinolizin-11-one, 10-acetyl-2,3,6,7-tetrahydro-;5-acetyl-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraen-4-one;10-Acetyl-2,3,6,7-tetrahydro-1H,5H,11H-(1)benzopyrano(6,7,8-ij)quinolizin-11-one;10-acetyl-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one;coumarin-334;10-ACETYL-2,3,6,7-TETRAHYDRO-1H,5H,11H-1-BENZOPYRANO(6,7,8-IJ)QUINOLIZIN-11-ONE;UNII-2773GTW04S;SCHEMBL2843124;DTXSID9069053;Coumarin 334, Dye content 99 %;CM 334;STL512104;AKOS000512249;AS-56425;C 334;CS-0241890;EU-0033311;FT-0624078;D95947;EN300-240268;Z56758353;F0348-0071;3-Acetyl-6,7,9,10-tetrahydro-8H,11H-quinolizino[9,9a, 1-gh]coumarin;10-acetyl-2,3,6,7-tetrahydro-1H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11(5H)-one;5-acetyl-3-oxa-13-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),5,8-tetraen-4-one

Chemical Property of Coumarin 334

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Vapor Pressure: 1.46E-12mmHg at 25°C
• Melting Point: 181-184 ºC
• Refractive Index: 1.647
• Boiling Point: 559.8°C at 760mmHg
• PKA: 5.37±0.40(Predicted)
• Flash Point: 292.4°C
• PSA: 50.52000
• Density: 1.33g/cm³
• LogP: 2.75940
• Water Solubility.: NEGLIGIBLE
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 283.12084340
• Heavy Atom Count: 21
• Complexity: 512

Purity/Quality:

99% ^*data from raw suppliers

Coumarin 334 ^*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

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Coumarin Dyes
• Canonical SMILES: CC(=O)C1=CC2=CC3=C4C(=C2OC1=O)CCCN4CCC3
• Uses: Suitable as a laser dye. Coumarin 334 is a laser dye with an absorption maximum of 452 nm. Dyes and metabolites.

Technology Process of Coumarin 334

There total 8 articles about Coumarin 334 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: 79.0%

9-formyl-8-hydroxyjulolidine (63149-33-7) + ethyl acetoacetate (141-97-9) → 10-acetyl-2,3,6,7-tetrahydro-1H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-11(5H)-one (55804-67-6)

Guidance literature:

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

Reference yield:

8-hydroxyjulolidine (41175-50-2) → 10-acetyl-2,3,6,7-tetrahydro-1H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-11(5H)-one (55804-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trichlorophosphate / 0 - 5 °C

2: piperidine / ethanol / Reflux

With piperidine; trichlorophosphate; In ethanol;

DOI:10.1002/chem.201303903

Reference yield:

m-Hydroxyaniline (591-27-5) → 10-acetyl-2,3,6,7-tetrahydro-1H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-11(5H)-one (55804-67-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium carbonate / N,N-dimethyl-formamide / Reflux

2: trichlorophosphate / Reflux

3: morpholine / ethanol / Reflux

With morpholine; sodium carbonate; trichlorophosphate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.jphotochem.2017.09.072

upstream raw materials:

m-Anisidine

8-methoxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline

8-hydroxyjulolidine

9-formyl-8-hydroxyjulolidine

Downstream raw materials:

coumarin-343

Refernces

• 1、 Gan, Yabing,Li, Haitao,Liu, Meiling,Yao, Shouzhuo,Yin, Guoxing,Yin, Peng,Yu, Ting,Zhang, Youyu,Zhou, Li. "A novel fluorescent probe with dual-sites for simultaneously monitoring metabolisms of cysteine in living cells and zebrafishes". . . Retrieved 2020.
• 2、 Bu, Dandan,Li, Zhanxian,Ren, Haohui,Yu, Mingming,Zhang, Hongyan,Zhang, Qiang. "Synthesis of a NIR fluorescent dye and its application for rapid detection of HSO3? in living cells". . . Retrieved 2021/09/04.