| Identification | More | [Name]
N-Carbethoxyphthalimide | [CAS]
22509-74-6 | [Synonyms]
1,3-DIOXO-1,3-DIHYDRO-ISOINDOLE-2-CARBOXYLIC ACID ETHYL ESTER
1,3-DIOXO-2-ISOINDOLINECARBOXYLIC ACID ETHYL ESTER
CARBETHOXYPHTHALIMIDE
CPI
ECPT
ETHYL 1,3-DIHYDRO-1,3-DIOXO-2H-ISOINDOLE-2-CARBOXYLATE
ETHYL 1,3-DIOXO-2-ISOINDOLINECARBOXYLATE
ETHYL 1,3-DIOXOISOINDOLINE-2-CARBOXYLATE
LABOTEST-BB LT00451715
N-CARBETHOXYPHTHALIMIDE
N-CARBOETHOXYPHTHALIMIDE
NEFKEN'S REAGENT
NEFKENS' REAGENT
N-ETHOXYCARBONYLPHTHALIMIDE
PHTHALIMIDE-N-CARBOXYLIC ACID ETHYL ESTER
TIMTEC-BB SBB007660
1,3-dihydro-1,3-dioxo-2h-isoindole-2-carboxylicaciethylester
1,3-dioxo-2-isoindolinecarboxylicaciethylester
2-Isoindolinecarboxylic acid, 1,3-dioxo-, ethyl ester
Ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate | [EINECS(EC#)]
245-048-5 | [Molecular Formula]
C11H9NO4 | [MDL Number]
MFCD00005893 | [Molecular Weight]
219.19 | [MOL File]
22509-74-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystalline powder | [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. ]
0-6°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) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P264b-P270-P301+P312-P330-P403+P233-P501c | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
NR3459500
| [F ]
10 | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
IRRITANT | [HS Code ]
29251995 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Dam. 1
Skin Irrit. 2
Skin Sens. 1 |
| Hazard Information | Back Directory | [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 |
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