4-Hydroxyindan-1-one Chemical Properties

Melting point:

242-244 °C (lit.)

Boiling point:

307.6±31.0 °C(Predicted)

Density 

1.305±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in ethanol. (25mg/ml)

form 

powder to crystal

pka

9.22±0.20(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C9H8O2/c10-8-3-1-2-6-7(8)4-5-9(6)11/h1-3,10H,4-5H2

InChIKey

CKSCMRNFDBWFND-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(O)=CC=C2)CC1

CAS DataBase Reference

40731-98-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29145090

MSDS

• Language:English Provider:SigmaAldrich

4-Hydroxyindan-1-one Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

4-Hydroxy-1-indanone is a hydroxylated indanone used for synthesis. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuffs.

Synthesis

General procedure for the synthesis of 4-hydroxy-1-indanone from hydrogenated cinnamic acid lactone: A mixture of aluminum chloride (90.0 g, 676 mmol) and sodium chloride was stirred at 150 °C until the solid was completely dissolved, followed by the slow dropwise addition of hydrogenated cinnamic acid lactone (20.0 g, 135 mmol). After the dropwise addition, the reaction mixture was warmed to 200 °C and stirred continuously for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water (500 mL), followed by filtration to collect the crude product. The crude product was purified by recrystallization to afford 4-hydroxy-1-indanone (19 g, 95% yield) as a gray solid. The structure of the compound was confirmed by the following spectral data: mass spectrum (ESI positive ion mode) m/z 149.5 [M + H]+; 1H NMR (400 MHz, CDCl3) δ (ppm): 7.41-7.38 (m, 1H), 7.24-7.19 (m, 1H), 6.80-6.79 (m, 1H), 6.78-6.77 (d , 1H, J = 4.0 Hz), 5.46 (br, 1H), 3.06-3.03 (m, 2H), 2.69-2.66 (m, 2H).

References

[1] Patent: WO2014/19344, 2014, A1. Location in patent: Paragraph 00820
[2] Patent: WO2014/82380, 2014, A1. Location in patent: Paragraph 00314; 00315
[3] Patent: WO2014/82379, 2014, A1. Location in patent: Page/Page column 112; 113
[4] Patent: WO2014/131315, 2014, A1. Location in patent: Page/Page column 112
[5] Patent: US2015/79028, 2015, A1. Location in patent: Paragraph 2389; 2390; 2391; 2392; 2393

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