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

InChIKey

VRHAQNTWKSVEEC-UHFFFAOYSA-N

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 Information

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 

Yes

HazardClass 

IRRITANT

HS Code 

29251995

MSDS

• Language:English Provider:Ethyl phthalimidocarboxylate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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(22509-74-6)Related Product Information

• O-Phthalimide
• Ethanol
• Ethyl acetate
• Ethyl oleate
• Ethyl pyruvate
• N-Chlorosuccinimide
• ISOXADIFEN-ETHYL
• 4-Nitrophthalimide
• Dispersing agent 155
• Ethylparaben
• Ethyl acrylate
• Ethyl formate
• Ethyl cyanoacetate
• Bismaleimide
• Succinimide
• N-Methylphthalimide
• N-Hydroxyphthalimide
• Potassium phthalimide