4 7-DIMETHOXY-1-INDANONE 97 Chemical Properties

Melting point:

122-125 °C (lit.)

Boiling point:

352.6±42.0 °C(Predicted)

Density 

1.179±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

Appearance

Light yellow to yellow Solid

Safety Information

WGK Germany 

3

HS Code 

2914500090

4 7-DIMETHOXY-1-INDANONE 97 Usage And Synthesis

Uses

4,7-Dimethoxy-1-indanone acts as a reagent for the synthesis and biological evaluation of indenopyrazine dicarbonitrile as inhibitors of deubiquitinating enzymes.

Definition

ChEBI: 4,7-dimethoxy-2,3-dihydroinden-1-one is a member of indanones.

Synthesis

The general procedure for the synthesis of 4,7-dimethoxy-1-indanone from 2,5-dimethoxybenzenepropanoic acid was as follows: a mixture of 2,5-dimethoxybenzenepropanoic acid (4.68 g, 22.3 mmol) and polyphosphoric acid (PPA, 50.87 g, 24.8 mL) was stirred and reacted for 4.0 h at 80°C. Upon completion of the reaction, the mixture was slowly poured into 250 mL of ice water and extracted with ethyl acetate (EtOAc, 100 mL x 5). The organic layers were combined, washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) and brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (v/v = 3/1) as eluent to afford 4,7-dimethoxy-1-indanone as a light yellow solid (3.0 g, 70.0% yield). The structure of the compound was confirmed by the following spectral data: mass spectrum (MS, ESI) m/z: 193.2 [M + H]+; 1H NMR (400 MHz, CDCl3) δ 7.52 (s, 1H), 6.87 (s, 1H), 3.90 (s, 3H), 3.88 (s, 3H), 3.00-2.97 (m, 2H), 2.68- 2.65 (m, 2H).

References

[1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 1051 - 1057
[2] Patent: WO2014/82379, 2014, A1. Location in patent: Page/Page column 139; 140; 141
[3] Patent: EP2730572, 2015, B1. Location in patent: Paragraph 0259; 0261
[4] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 8, p. 905 - 915
[5] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 8, p. 1052 - 1062

4 7-DIMETHOXY-1-INDANONE 97(52428-09-8)Related Product Information

• 1-Indanone
• 4,7-DIMETHOXY-2-METHYL-INDAN-1-ONE
• 3-(2,5-DIMETHOXY-PHENYL)-PROPIONALDEHYDE
• 4-HYDROXY-7-METHOXYINDAN
• 7-HYDROXY-4-METHOXY-INDAN-1-ONE
• 4 7-DIMETHOXY-1-INDANONE 97
• 2-BROMO-2,3-DIHYDRO-4,7-DIMETHOXY-1H-INDEN-1-ONE
• 4-METHOXY-1-INDANONE
• 4-Hydroxyindan-1-one