3-(1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-PROPIONALDEHYDE Chemical Properties

Melting point:

136-141 ºC

Boiling point:

352.7±25.0 °C(Predicted)

Density 

1.319±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

solid

pka

-2.24±0.20(Predicted)

color 

White

InChI

InChI=1S/C11H9NO3/c13-7-3-6-12-10(14)8-4-1-2-5-9(8)11(12)15/h1-2,4-5,7H,3,6H2

InChIKey

IBSDSIHTMABATG-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC=C2)C(=O)N1CCC=O

CAS DataBase Reference

2436-29-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43

Safety Statements 

26-36/37

HS Code 

2909498090

Toxicity

mouse,LD50,intraperitoneal,1055mg/kg (1055mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Journal of Pharmaceutical Sciences. Vol. 57, Pg. 815, 1968.

3-(1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-PROPIONALDEHYDE Usage And Synthesis

Description

3-(1,3-Dioxoisoindol-2-yl)propanal is an aldehyde organic compound, which can be used as a pharmaceutical intermediate.

Chemical Properties

White powdery crystal, which is easy to absorb moisture.

Uses

3-(1,3-Dioxoisoindol-2-yl)propanal is a key intermediate in the preparation of atorvastatin (Lipitor).

Synthesis

Step 2. Preparation of 3-(1,3-dioxoisoindolin-2-yl)propanal A mixture of 2-(3-hydroxypropyl)isoindoline-1,3-dione (2.0 g, 8.76 mmol) with IBX (8.2 g, 29.27 mmol) in 60 mL of ethyl acetate (EA) was refluxed for 2 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated to afford 3-(1,3-dioxoisoindolin-2-yl)propionaldehyde (2.0 g, yield: 100%) as a white solid. NMR (500 MHz, CDCl3): δ 9.82 (s, 1H), 7.84-7.86 (m, 2H), 7.72-7.74 (m, 2H), 4.04 (t, J = 7.0 Hz, 2H), 2.87-2.89 (m, 2H) ppm. MS (ESI): m/z 553.7 [M + 1]+.

References

[1] Patent: WO2012/82436, 2012, A2. Location in patent: Page/Page column 245-246
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 32, p. 6094 - 6104
[3] Journal of the American Chemical Society, 2006, vol. 128, # 12, p. 4023 - 4034
[4] Tetrahedron, 2002, vol. 58, # 9, p. 1719 - 1737
[5] Helvetica Chimica Acta, 2005, vol. 88, # 10, p. 2610 - 2616

3-(1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-PROPIONALDEHYDE(2436-29-5)Related Product Information

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