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| | N-Carbethoxyphthalimide Basic information |
| Product Name: | N-Carbethoxyphthalimide | | Synonyms: | 1,3-dihydro-1,3-dioxo-2h-isoindole-2-carboxylicaciethylester;1,3-dioxo-2-isoindolinecarboxylicaciethylester;N-(Carboethoxy)phthalimide~Nefkens;Ethyl phthalimidocarboxylate;N-Ethoxycarbonylphthalimide [for Peptide synthesis];N-Carbethoxyphthalimide, 98+%;N-Carbethoxyphthalimide, 99+%;2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester | | CAS: | 22509-74-6 | | MF: | C11H9NO4 | | MW: | 219.19 | | EINECS: | 245-048-5 | | Product Categories: | Biochemistry;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Peptide Synthesis;Protection & Derivatization Reagents (for Synthesis);Protective Reagents (Peptide Synthesis);Synthetic Organic Chemistry | | Mol File: | 22509-74-6.mol |  |
| | N-Carbethoxyphthalimide Chemical Properties |
| Melting point | 90-92 °C(lit.) | | Boiling point | 360°C (rough estimate) | | density | 1.3219 (rough estimate) | | vapor pressure | 0.003-0.006Pa at 20-25℃ | | refractive index | 1.4950 (estimate) | | storage temp. | Inert atmosphere,2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Crystalline Powder | | pka | -3.02±0.20(Predicted) | | color | White | | Water Solubility | insoluble | | BRN | 196340 | | InChI | 1S/C11H9NO4/c1-2-16-11(15)12-9(13)7-5-3-4-6-8(7)10(12)14/h3-6H,2H2,1H3 | | InChIKey | VRHAQNTWKSVEEC-UHFFFAOYSA-N | | SMILES | CCOC(=O)N1C(=O)c2ccccc2C1=O | | LogP | 1.1 at 20℃ and pH6.6-6.9 | | CAS DataBase Reference | 22509-74-6(CAS DataBase Reference) | | NIST Chemistry Reference | 2H-isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester(22509-74-6) | | EPA Substance Registry System | 2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester (22509-74-6) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38-20/21/22 | | Safety Statements | 22-24/25-36/37/39-26-36 | | WGK Germany | 3 | | RTECS | NR3459500 | | F | 10 | | TSCA | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29251995 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Dam. 1
Skin Irrit. 2
Skin Sens. 1 |
| | N-Carbethoxyphthalimide Usage And Synthesis |
| Chemical Properties | White crystalline powder | | Uses | N-Carbethoxyphthalimide is used in the synthetic preparation of a novel dual binders as potent, selective, and orally bioavailable tankyrase inhibitors. | | Preparation | N-Carbethoxyphthalimide is prepared for: addition of Ethyl Chloroformate to a cold solution of Phthalimide and Triethylamine in DMF; alkylation of potassium phthalimide with ethyl chloroformate.
| | Synthesis | GENERAL METHOD: 3-Hydroxy-1H-isoindol-1-one (7.36 g, 50.00 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF, 25 mL) and triethylamine (TEA, 9 mL, 65.00 mmol) was added. The reaction system was cooled to 0 °C, followed by slow dropwise addition of ethyl chloroformate (5.7 mL, 60.00 mmol). The reaction mixture was stirred at room temperature for 2 h and then poured into ice water. The precipitate was collected by filtration and the solid product was washed with cold water and dried to give N-ethoxycarbonylphthalimide (8.67 g, 79.1% yield) as a white solid. The melting point was 81.4-83.6 ℃. Nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3, 400 MHz) δ: 1.44 (s, 3H, CH3), 4.48 (q, J = 7.1 Hz, 2H, CH2), 7.80-7.85 (m, 2H, Ar-H), 7.93-7.99 (m, 2H, Ar-H). Mass spectrum (ESI): m/z 220.1 [M + H]+. | | storage |
No special handling conditions or precautions are required.
| | Purification Methods | Crystallise the imide from toluene/pet ether (or *benzene/pet ether). It is partly soluble in Et2O, *benzene and CHCl3. [Heller & Jacobsohn Chem Ber 54 1112 1921, Beilstein 21/10 V 428.] | | References | [1] Journal of Organic Chemistry, 1980, vol. 45, # 1, p. 174 - 175
[2] Organic Letters, 2015, vol. 17, # 23, p. 5846 - 5849
[3] Synthetic Communications, 1980, vol. 10, # 8, p. 611 - 614
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 11, p. 2576 - 2588
[5] Patent: CN105732683, 2016, A. Location in patent: Paragraph 0090; 0091; 0092; 0093 |
| | N-Carbethoxyphthalimide Preparation Products And Raw materials |
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