9-Fluorenone-2-carboxylic acid

9-Fluorenone-2-carboxylic acid Property

Melting point:

>300 °C (lit.)

Boiling point:

325.61°C (rough estimate)

Density 

1.2337 (rough estimate)

refractive index 

1.5400 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

Fine Powder

pka

3.85±0.20(Predicted)

color 

Yellow

CAS DataBase Reference

784-50-9(CAS DataBase Reference)

NIST Chemistry Reference

9-Fluorenone-2-carboxylic acid(784-50-9)

Safety

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29183000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

9-Fluorenone-2-carboxylic acid Chemical Properties,Usage,Production

Chemical Properties

yellow fine powder

Uses

9-Fluorenone-2-carboxylic Acid (cas# 784-50-9) is a compound useful in organic synthesis.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 3958, 1948 DOI: 10.1021/ja01191a530
Organic Syntheses, Coll. Vol. 3, p. 420, 1955

Synthesis

General procedure for the synthesis of 9-fluorenone-2-carboxylic acid from the compound (CAS: 3096-44-4): potassium hydroxide (1.6 g, 29.4 mmol) was added to a mixture of methanol (7 mL) and water (7 mL) containing compound 12 (200 mg, 0.98 mmol), and the reaction mixture was stirred for 6 hours at 110 °C. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure. The pH was adjusted to 3 with 1 N hydrochloric acid and the mixture was extracted with ethyl acetate (30 mL x 3). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated to afford the target product 9-fluorenone-2-carboxylic acid (200 mg, 91% yield) as a yellow solid.1H NMR (400 MHz, DMSO-d6) δ 13.30 (s, 1H), 8.19 (d, J = 7.6 Hz, 1H), 8.03 (s, 1H), 7.97-9.89 ( m, 2H), 7.72-7.64 (m, 2H), 7.50-7.44 (m, 1H).

References

[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 22, p. 5861 - 5872
[2] Patent: CN104557862, 2017, B. Location in patent: Paragraph 0102-0104; 0109-0110