ChemicalBook CAS DataBase List 22509-74-6

22509-74-6

Name	N-Carbethoxyphthalimide
CAS	22509-74-6
EINECS(EC#)	245-048-5
Molecular Formula	C11H9NO4
MDL Number	MFCD00005893
Molecular Weight	219.19
MOL File	22509-74-6.mol

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

Chemical Properties

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

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 . less more
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 . less more
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

Raw materials And Preparation Products

Hazard Information

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

Material Safety Data Sheet(MSDS)

Spectrum Detail

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