41267-76-9

Basic information

• Product Name: Coumarin 102
• Synonyms: 1h,5h,11h-(1)benzopyrano(6,7,8-ij)quinolizin-11-one,2,3,6,7-tetrahydro-9-methy;1h,5h,11h-[1]benzopyrano[6,7,8-ij]quinolizin-11-one,2,3,6,7-tetrahydro-9-methy;2,3,5,6-1h,4h-tetrahydro-8-methylquinolazino-(9,9a,1-gh)coumarin;c102;8-Methyl-2,3,5,6-1H,4H-tetrahydroquinolizino[9,9a,1-gh]coumarin;8-METHYL-2,3,5,6-TETRAHYDRO-1,H,4H-11-OXA-3A-AZA-BENZO(DE)ANTHRACEN-10-ONE;2,3,5,6-1H,4H-TETRAHYDRO-8-METHYLQUINOLIZINO-[9,9A,1GH]COUMARIN;2,3,6,7-TETRAHYDRO-9-METHYL-1H,5H-QUINOLIZINO(9,1-GH)COUMARIN
• CAS NO: 41267-76-9
• Molecular Formula: C₁₆H₁₇NO₂
• Molecular Weight: 255.31
• EINECS: 255-285-6
• Mol File: 41267-76-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 152-156 °C(lit.)
• Boiling Point: 398.54°C (rough estimate)
• Flash Point: 194.905 °C
• Appearance: yellow needle-like crystals
• Density: 1.0699 (rough estimate)
• Vapor Pressure: 1.25E-09mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• PKA: 5?+-.0.40(Predicted)
• BRN: 4818243
• CAS DataBase Reference: Coumarin 102(CAS DataBase Reference)
• NIST Chemistry Reference: Coumarin 102(41267-76-9)
• EPA Substance Registry System: Coumarin 102(41267-76-9)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26
• WGK Germany: 3
• RTECS: DJ3320000
• Hazardous Substances Data: 41267-76-9(Hazardous Substances Data)

Usage

Description

Coumarin 102 (C102) is a laser dye characterized by its yellow needle-like crystals and amino groups in the seventh position. It exhibits a spectrum in the green and blue regions, with its quantum efficiency being dependent on the orientation of the amino groups.

Uses

Used in Laser Applications:
Coumarin 102 is used as a laser dye for its ability to produce a spectrum in the green and blue regions, making it suitable for various laser applications.
Used in Fluorescent Probe Applications:
Coumarin 102 is used as a fluorescent probe for studying solvent relaxation dynamics, providing valuable insights into the behavior of solvents under different conditions.
Used in Research and Diagnostics:
Due to its fluorescent properties, Coumarin 102 can be employed in research and diagnostics, particularly in the field of biochemistry and molecular biology, where it can be used to label and track specific molecules or cellular components.

InChI:InChI=1/C16H17NO2/c1-10-8-14(18)19-16-12-5-3-7-17-6-2-4-11(15(12)17)9-13(10)16/h8-9H,2-7H2,1H3

Synthetic route

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

Conditions	Yield
With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride In 1,4-dioxane; 1,2-dichloro-ethane at 20℃; Reagent/catalyst; Sealed tube; regioselective reaction;	91%
With C64H108AuClN2O33 In water at 37℃; for 42h; Reagent/catalyst; Inert atmosphere; Schlenk technique; regioselective reaction;	52%

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)

Conditions	Yield
With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride In 1,4-dioxane; 1,2-dichloro-ethane at 20℃; Reagent/catalyst; Sealed tube; regioselective reaction;	90%

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

Conditions	Yield
With triisopropoxytitanium(IV) chloride In toluene for 16h; Pechmann condensation; Reflux;	73%

8-hydroxyjulolidine (41175-50-2) + ethyl acetoacetate (141-97-9) → coumarin 102 (41267-76-9)

Conditions	Yield
With sulfuric acid at 130℃; for 0.2h; Irradiation;	62%

morpholine (110-91-8) + formaldehyd (50-00-0) + coumarin 102 (41267-76-9) → 8-Methyl-9-morpholin-4-ylmethyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one (142878-51-1)

Conditions	Yield
With acetic acid	92%

coumarin 102 (41267-76-9) → 9-bromo-8-methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one (127321-52-2)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile for 0.166667h;	88%
With N-Bromosuccinimide In acetonitrile

coumarin 102 (41267-76-9) → 9-Chloro-8-methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one (133590-31-5)

Conditions	Yield
With copper dichloride In acetonitrile for 0.5h; Heating;	85%

coumarin 102 (41267-76-9) → 2,3,6,7-tetrahydro-9-methyl-10-iodo-1H,5H-quinolizino<9,9a,1-gh>coumarin (133590-32-6)

Conditions	Yield
With pyridine; iodine In 1,4-dioxane	82%

coumarin 102 (41267-76-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6-methyl-4-oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraene-5-carbaldehyde

Conditions	Yield
With trichlorophosphate for 1.083h; Inert atmosphere;	80.8%

formaldehyd (50-00-0) + coumarin 102 (41267-76-9) + N-methyl-1-octadecylamine (2439-55-6) → 8-Methyl-9-[(methyl-octadecyl-amino)-methyl]-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one (138977-14-7)

Conditions	Yield
With acetic acid	72%

formaldehyd (50-00-0) + coumarin 102 (41267-76-9) + 1-amino-2-propene (107-11-9) → 9-Allylaminomethyl-8-methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one (142878-49-7)

Conditions	Yield
With acetic acid	68%

formaldehyd (50-00-0) + coumarin 102 (41267-76-9) + benzylamine (100-46-9) → 9-(Benzylamino-methyl)-8-methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one (142878-50-0)

Conditions	Yield
With acetic acid	66%

formaldehyd (50-00-0) + coumarin 102 (41267-76-9) + 3-(Benzylamino-methyl)-7-diethylamino-4-methyl-chromen-2-one (142878-41-9) → 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 (142878-54-4)

Conditions	Yield
With acetic acid at 75℃; for 1.5h;	36%

coumarin 102 (41267-76-9) + iodobenzene (591-50-4) → 8-Methyl-9-phenyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one (131882-58-1)

Conditions	Yield
In acetonitrile Quantum yield; Irradiation; Et3N;	35%
With triethylamine In acetonitrile Irradiation;	35%

styrene (292638-84-7) + coumarin 102 (41267-76-9) → 1-endo-phenyl-12b-methyl-1,2,6,7,10,11-hexahydro-3H,5H,9H--cyclobutabenzopyrano<6,7,8-ij>quinolizin-3-one (121262-35-9)

Conditions	Yield
In acetonitrile for 10h; Irradiation;	32%
In acetonitrile Quantum yield; Irradiation;

coumarin 102 (41267-76-9) + ethyl bromoacetate (105-36-2) → (8-Methyl-10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-9-yl)-acetic acid ethyl ester (114145-46-9)

Conditions	Yield
With triethylamine In acetonitrile Irradiation;	29%

2-iodo-propane (75-30-9) + coumarin 102 (41267-76-9) → 10-isopropyl-9-methyl-2,3,6,7-tetrahydro-1H,5H,11H-chromeno<6,7,8-i,j>quinolizin-11-one (118132-33-5)

Conditions	Yield
With triethylamine In acetonitrile Irradiation;	20%

coumarin 102 (41267-76-9) → 9-Fluoro-8-methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one (137126-05-7)

Conditions	Yield
With xenon difluoride In acetonitrile at 0℃; for 0.5h;	20%

formaldehyd (50-00-0) + coumarin 102 (41267-76-9) + 9-(Benzylamino-methyl)-8-methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one (142878-50-0) → C41H43N3O4 (142878-55-5)

Conditions	Yield
With acetic acid at 75℃; for 1.5h;	16%

piperidine (110-89-4) + coumarin 102 (41267-76-9) → C21H27N2O(1+)*BF4(1-)

Conditions	Yield
With triethyloxonium fluoroborate 1) CH2Cl2, 30 deg C, 20-30 min, 2) 2-3h, reflux; Yield given. Multistep reaction;

coumarin 102 (41267-76-9) + bis(heptafluorobutyryl) peroxide (336-64-1) → 10-(heptafluoropropyl)-2,3,6,7-tetrahydro-9-methyl-1H,5H,11H-pyrano<2',3'-4,5>benzo<1,2,3-ij>quinolizine-11-one (137516-25-7)

Conditions	Yield
In dichloromethane; 1,1,2-Trichloro-1,2,2-trifluoroethane for 4h; Heating;	15 % Turnov.

coumarin 102 (41267-76-9) + sodium acetylacetonate (15435-71-9, 1118-67-8) → 3-(8-Methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-ylidene)-pentane-2,4-dione (118967-42-3)

Conditions	Yield
With triethyloxonium fluoroborate 1). 40 min. 20 deg C, 2)4 hrs. 50 deg C; Yield given. Multistep reaction;

coumarin 102 (41267-76-9) + sodium diethylmalonate (996-82-7) → 2-(8-Methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-ylidene)-malonic acid diethyl ester (118967-43-4)

Conditions	Yield
With triethyloxonium fluoroborate 1). 40 min. 20 deg C, 2)4 hrs. 50 deg C; Yield given. Multistep reaction;

coumarin 102 (41267-76-9) + sodium ethyl acetylacetate enolate (1007476-32-5) → 2-[8-Methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-(10Z)-ylidene]-3-oxo-butyric acid ethyl ester (118967-44-5)

Conditions	Yield
With triethyloxonium fluoroborate 1). 40 min. 20 deg C, 2)4 hrs. 50 deg C; Yield given. Multistep reaction;

coumarin 102 (41267-76-9) + indan-1,3-dione sodium salt (118967-48-9) → 2-(8-Methyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-ylidene)-indan-1,3-dione (118967-45-6)

Conditions	Yield
With triethyloxonium fluoroborate 1). 40 min. 20 deg C, 2)4 hrs. 50 deg C; Yield given. Multistep reaction;

coumarin 102 (41267-76-9) + aniline (62-53-3) → C22H23N2O(1+)*BF4(1-)

Conditions	Yield
With triethyloxonium fluoroborate 1) CH2Cl2, 30 deg C, 20-30 min, 2) 2-3h, reflux; Yield given. Multistep reaction;

coumarin 102 (41267-76-9) → C41H43N3O4 (142878-55-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / glacial acetic acid 2: 16 percent / acetic acid / 1.5 h / 75 °C View Scheme

Upstream product

• 41175-50-2 8-hydroxyjulolidine 
• 141-97-9 ethyl acetoacetate 
• 1386264-12-5 8-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine) 5-(tert-butoxycarbonylamino)hex-2-ynoate 
• 1386264-02-3 8-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine) but-2-ynoate 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 142878-55-5 C₄₁H₄₃N₃O₄ 
• 142878-54-4 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 
• 142730-53-8 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 

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