2-METHOXY-9H-CARBAZOLE Chemical Properties

Melting point:

239℃

Boiling point:

392.2±15.0 °C(Predicted)

Density 

1.232±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

16.74±0.30(Predicted)

color 

White to Almost white

λmax

209nm(MeOH)(lit.)

InChI

InChI=1S/C13H11NO/c1-15-9-6-7-11-10-4-2-3-5-12(10)14-13(11)8-9/h2-8,14H,1H3

InChIKey

MDKVPSJRUXOFFV-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C2=C1C=C(OC)C=C2

CAS DataBase Reference

6933-49-9

Safety Information

HS Code 

2933.99.8290

2-METHOXY-9H-CARBAZOLE Usage And Synthesis

Synthesis

To a suspension of copper(I)iodide (7.7 g, 40.6 mmol, 2.0 equiv) and 2-bromo-9H carbazole (5.0 g, 20.3 mmol, 1.0 equiv) in anhydrous DMF (22 mL), sodium methanolate (61 mL, 267 mmol, 13 equiv) was added. The reaction mixture was stirred for 4 hours at 120 °C. After completion (judged by TLC) the reaction mixture was filtrated through celites and directly adsorbed on silica. Purification by chromatography on silica (CHCl3 100 %) afforded the 2-methoxy-9H-carbazole (3.9 g, 19.5 mmol, 96 % yield) as a white solid.¹

References

[1] Limberg, F. R. P., Miasojedovas, A., Pingel, P., Reisbeck, F., Janietz, S., Monkman, A. P., & Krüger, H. (2015). Hole-transporting side-chain polystyrenes based on TCTA with tuned glass transition and optimized electronic properties†. RSC Advances, 101, 83122–83128. https://doi.org/10.1039/C5RA12963J

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