9-ACETYLCARBAZOLE 97 Chemical Properties

Melting point:

77-79 °C (lit.)

Boiling point:

348.61°C (rough estimate)

Density 

1.1580

refractive index 

1.6400 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Toluene

form 

powder to crystal

color 

White to Almost white

InChI

1S/C14H11NO/c1-10(16)15-13-8-4-2-6-11(13)12-7-3-5-9-14(12)15/h2-9H,1H3

InChIKey

CADSTRJVECIIAT-UHFFFAOYSA-N

SMILES

CC(=O)n1c2ccccc2c3ccccc13

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933.99.8290

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

9-ACETYLCARBAZOLE 97 Usage And Synthesis

Synthesis

Vinyl acetate (1a, 167 mg, 1 mmol) and carbazole (2, 430 mg, 5 mmol) were mixed with [Ir(Cl)(cod)]2 (6.7 mg, 0.01 mmol), Na2CO3 (127 mg, 1.2 mmol) and toluene (1 mL) under argon protection and the reaction was stirred for 15 h at 100 °C. The reaction was carried out by GC analysis. The conversion and yield of the product were calculated by gas chromatography (GC) analysis with internal standard method, and the yield of 1-(9H-carbazol-9-yl)ethanone (3a) was obtained as 96%. Product 3a was purified by column chromatography (using 230-400 mesh silica gel with hexane containing 5% Et3N as eluent) in a final yield of 94% (181 mg). For product 3e, the separation was carried out by column chromatography only (using 70-230 mesh alumina and hexane as eluent).

References

[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, vol. 19, # 11, p. 1192 - 1197
[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, # 11, p. 1504 - 1509
[3] Synlett, 2017, vol. 28, # 6, p. 719 - 723

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