2,3,6,7-Tetrahydro-1H,5H-benzo[ij]quinolizine-9-carboxaldehyde Chemical Properties

Melting point:

83 °C

Boiling point:

404.8±44.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.15±0.20(Predicted)

color 

Light orange to Yellow to Green

InChI

InChI=1S/C13H15NO/c15-9-10-7-11-3-1-5-14-6-2-4-12(8-10)13(11)14/h7-9H,1-6H2

InChIKey

XIIVBURSIWWDEO-UHFFFAOYSA-N

SMILES

C12=CC(C=O)=CC3=C1N(CCC3)CCC2

EPA Substance Registry System

1H,5H-Benzo[ij]quinolizine-9-carboxaldehyde, 2,3,6,7-tetrahydro- (33985-71-6)

Safety Information

RTECS 

DK1480000

HS Code 

2933.49.7000

2,3,6,7-Tetrahydro-1H,5H-benzo[ij]quinolizine-9-carboxaldehyde Usage And Synthesis

Description

9-Julolidinecarboxaldehyde is a fluorescent probe.

Synthesis

Julolidine (0.5 g, 2.89 mmol), N,N-dimethylformamide (0.255 g, 3.49 mmol), and phosphorous trichloride (0.535 g, 3.49 mmol) were dissolved in dichloromethane (15 mL), and the mixture was stirred for 4 h at room temperature under argon protection. The color of the solution changed to green during the reaction and the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction was quenched with water and the crude product was subsequently extracted with 2 M sodium hydroxide solution and ether. The organic phase was washed twice with water, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography with 40%-50% ether/hexane as eluent to give 0.48 g (83.08% yield) of 1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline-9-carboxaldehyde as a light-yellow solid (up to 92% when 1.5 g of julonidine was used). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 9.597 (s, 1H), 7.29 (s, 1H), 3.308 (t, J = 57 Hz, 4H), 2.787 (t, J = 62 Hz, 4H), 2.002-1.92 (m, J = 63 Hz, 4H).

References

[1] Tetrahedron, 2007, vol. 63, # 1, p. 103 - 114
[2] Organic Preparations and Procedures International, 2001, vol. 33, # 6, p. 603 - 613
[3] Journal of Nanoscience and Nanotechnology, 2015, vol. 15, # 11, p. 8813 - 8819
[4] Chemistry - A European Journal, 2010, vol. 16, # 30, p. 9257 - 9263
[5] Chemical Communications, 2014, vol. 50, # 78, p. 11507 - 11510

2,3,6,7-Tetrahydro-1H,5H-benzo[ij]quinolizine-9-carboxaldehyde(33985-71-6)Related Product Information

• 8-HYDROXYJULOLIDINE-9-ALDEHYDE
• Tetramethyljulolidine
• 1,1,7,7-TETRAMETHYL-2,3,6,7-TETRAHYDRO-1H,5H-PYRIDO[3,2,1-IJ] QUINOLINE
• Julolidine
• 9-Formyl-8-hydroxy-1,1,7,7-tetramethyljulolidine
• RARECHEM AL BF 0592
• 8-METHOXY-2,3,6,7-TETRAHYDRO-1H,5H-PYRIDO[3,2,1-IJ]QUINOLINE-9-CARBALDEHYDE
• RARECHEM AL BF 0792
• 7-(4-BROMOPHENYL)-3B,6,6A,7,9,9A,10,12A-OCTAHYDROCYCLOPENTA[C]CYCLOPENTA[4,5]PYRIDO[3,2,1-IJ]QUINOLINE-2-CARBOXYLIC ACID
• 2,3,6,7-Tetrahydro-1H,5H-benzo[ij]quinolizine-9-carboxaldehyde
• RARECHEM AL BE 0792
• RARECHEM AL BI 0592
• 1,1,7,7-Tetramethyljulolidine-9-carboxaldehyde
• 8-HYDROXYJULOLIDINE-9-ALDEHYDE
• RARECHEM AL BE 0592
• RARECHEM AL BI 0792