N-Carbethoxyphthalimide

Product Name: N-Carbethoxyphthalimide
CAS No.: 22509-74-6
Chemical Name: N-Carbethoxyphthalimide
Synonyms: CPI;N-ETHOXYCARBONYLPHTHALIMIDE;ETHYL 1,3-DIOXOISOINDOLINE-2-CARBOXYLATE;N-CARBOETHOXYPHTHALIMIDE;2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester;ECPT;ADIN-010;NEFKEN'S REAGENT;NEFKENS' REAGENT;N-CarbethoxyphthaL
CBNumber: CB5382202
Molecular Formula: C11H9NO4
Formula Weight: 219.19
MOL File: 22509-74-6.mol

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N-Carbethoxyphthalimide Property

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)

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: C5459
Product name: N-Carbethoxyphthalimide
Purity: 96%
Packaging: 25g
Price: $44.59
Updated: 2025/07/31

Sigma-Aldrich

Product number: C5459
Product name: N-Carbethoxyphthalimide
Purity: 96%
Packaging: 100g
Price: $114.8
Updated: 2025/07/31

TCI Chemical

Product number: C0683
Product name: N-Ethoxycarbonylphthalimide [for Peptide Synthesis]
Purity: >98.0%(N)
Packaging: 25g
Price: $39
Updated: 2025/07/31

TCI Chemical

Product number: C0683
Product name: N-Ethoxycarbonylphthalimide [for Peptide Synthesis]
Purity: >98.0%(N)
Packaging: 100g
Price: $104
Updated: 2025/07/31

TCI Chemical

Product number: C0683
Product name: N-Ethoxycarbonylphthalimide [for Peptide Synthesis]
Purity: >98.0%(N)
Packaging: 500g
Price: $310
Updated: 2025/07/31

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N-Carbethoxyphthalimide Chemical Properties,Usage,Production

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

136918-14-4

541-41-3

22509-74-6

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

Raw materials

Preparation Products

Methyl 7-amino-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate

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N-Carbethoxyphthalimide Suppliers

Americas 1 Belgium 2 China 166 Europe 1 Germany 7 India 10 Japan 12 Slovakia 1 South Korea 1 Switzerland 4 United Kingdom 14 United States 51 Global 270

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View Lastest Price from N-Carbethoxyphthalimide manufacturers

Henan Aochuang Chemical Co.,Ltd.

Product: N-Carbethoxyphthalimide 22509-74-6
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1ton
Release date: 2022-09-26

Career Henan Chemical Co

Product: N-Carbethoxyphthalimide 22509-74-6
Price: US $1.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 100KG
Release date: 2018-12-22

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<i>N</i>-Carbethoxyphthalimide

22509-74-6

22599-74-6

C11H9NO4

Carbonyl Compounds

Building Blocks

Cyclic Imides

Organic Building Blocks

Protection and Derivatization

Protecting and Derivatizing Reagents

Others