Coumarin 102

Base Information

• Chemical Name: Coumarin 102
• CAS No.: 41267-76-9
• Deprecated CAS: 53664-69-0,54576-75-9,865440-98-8,54576-75-9,865440-98-8
• Molecular Formula: C16H17NO2
• Molecular Weight: 255.316
• Hs Code.: 2934999090
• European Community (EC) Number: 255-285-6
• NSC Number: 290431
• UNII: 0M1GI783QT
• DSSTox Substance ID: DTXSID9068293
• Nikkaji Number: J320.038H
• Wikidata: Q27122741
• Mol file: 41267-76-9.mol

Synonyms:coumarin 480

Chemical Property of Coumarin 102

Chemical Property:

• Appearance/Colour: yellow needle-like crystals
• Vapor Pressure: 1.25E-09mmHg at 25°C
• Melting Point: 152-156 °C(lit.)
• Refractive Index: 1.647
• Boiling Point: 486.862 °C at 760 mmHg
• PKA: 5?+-.0.40(Predicted)
• Flash Point: 194.905 °C
• PSA: 33.45000
• Density: 1.284 g/cm³
• LogP: 2.86520
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 255.125928785
• Heavy Atom Count: 19
• Complexity: 431

Purity/Quality:

99% ^*data from raw suppliers

Coumarin 102 ^*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: CC1=CC(=O)OC2=C1C=C3CCCN4C3=C2CCC4
• Uses: Laser dye. Coumarin 102 is a fluorescent probe used in the study of solvent relaxation dynamics.

Technology Process of Coumarin 102

There total 5 articles about Coumarin 102 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: 91.0%

8-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine) but-2-ynoate (1386264-02-3) → coumarin 102 (41267-76-9,54576-75-9)

Guidance literature:

With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride; In 1,4-dioxane; 1,2-dichloro-ethane; at 20 ℃; Reagent/catalyst; regioselective reaction; Sealed tube;

DOI:10.1021/jo3006842

Reference yield: 90.0%

8-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine) 5-(tert-butoxycarbonylamino)hex-2-ynoate (1386264-12-5) → coumarin 102 (41267-76-9,54576-75-9)

Guidance literature:

With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride; In 1,4-dioxane; 1,2-dichloro-ethane; at 20 ℃; Reagent/catalyst; regioselective reaction; Sealed tube;

DOI:10.1021/jo3006842

Reference yield: 73.0%

8-hydroxyjulolidine (41175-50-2) + acetoacetic acid methyl ester (105-45-3) → coumarin 102 (41267-76-9,54576-75-9)

Guidance literature:

With triisopropoxytitanium(IV) chloride; In toluene; for 16h; Reflux;

DOI:10.1002/ejoc.201101117

upstream raw materials:

8-hydroxyjulolidine

ethyl acetoacetate

acetoacetic acid methyl ester

8-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine) but-2-ynoate

Downstream raw materials:

C₄₁H₄₃N₃O₄

9-{[Benzyl-(7-diethylamino-4-methyl-2-oxo-2H-chromen-3-ylmethyl)-amino]-methyl}-8-methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one

6-methyl-4-oxo-3-oxa-13-azatetracyclo[7.7.1.0^2,7.0^13,17]heptadeca-1,5,7,9⁽¹⁷⁾-tetraene-5-carbaldehyde

Refernces

• 1、 Vadola, Paul A.,Sames, Dalibor. "Catalytic coupling of arene C-H bonds and alkynes for the synthesis of coumarins: Substrate scope and application to the development of neuroimaging agents". . p. 7804 - 7814,11. Retrieved 2020/10/15.
• 2、 Frère, Stéphane,Thiéry, Valérie,Besson, Thierry. "Microwave acceleration of the Pechmann reaction on graphite/montmorillonite K10: Application to the preparation of 4-substituted 7-aminocoumarins". . p. 2791 - 2794. Retrieved 2007/10/03.