|
|
| | 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propionaldehyde Basic information |
| Product Name: | 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propionaldehyde | | Synonyms: | 3-(Phthalimid-1-yl)propanal;2H-Isoindole-2-propanal,1,3-dihydro-1,3-dioxo-;3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanal;3-(1,3-dioxo-2-isoindolinyl)propanal;.beta.-Phthalimidopropionaldehyde;2H-Isoindole-2-propanal, 1,3-dihydro-1,3-dioxo- (9CI);beta-Phthalimidopropionaldehyde;Phthalimide, N-(2-formylethyl)- | | CAS: | 2436-29-5 | | MF: | C11H9NO3 | | MW: | 203.19 | | EINECS: | | | Product Categories: | | | Mol File: | 2436-29-5.mol |  |
| | 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) |
| 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 Preparation Products And Raw materials |
|