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22509-74-6

Basic Information
CAS No.: 22509-74-6
Name: N-Carbethoxyphthalimide
Article Data: 26
Molecular Structure:
Molecular Structure of 22509-74-6 (N-Carbethoxyphthalimide)
Formula: C11H9NO4
Molecular Weight: 219.197
Synonyms: 2-Isoindolinecarboxylicacid, 1,3-dioxo-, ethyl ester (6CI,7CI,8CI);2-(Carbethoxy)phthalimide;Carbethoxyphthalimide;Ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate;EthylN-phthaloylcarbamate;N-(Ethoxycarbonyl)phthalimide;
EINECS: 245-048-5
Density: 1.398 g/cm3
Melting Point: 90-92 °C
Boiling Point: 353.871 °C at 760 mmHg
Flash Point: 167.815 °C
Solubility: insoluble in water
Appearance: White crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 36/37/38-20/21/22
Safety: 22-24/25-36/37/39-26
PSA: 63.68000
LogP: 1.37700
Synthetic route
541-41-3

chloroformic acid ethyl ester

1074-82-4

potassium phtalimide

22509-74-6

N-ethoxycarbonylphthalimide

Conditions
ConditionsYield
With 18-crown-6 ether In toluene at 90℃; for 1h;96%
With benzene
136918-14-4

phthalimide

541-41-3

chloroformic acid ethyl ester

22509-74-6

N-ethoxycarbonylphthalimide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide 1. 0-5 deg C, 90 min; 2. room temperature, 4 h;95%
With dmap; triethylamine In dichloromethane at -40℃; for 0.0833333h;94%
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Inert atmosphere;94%
67-56-1

methanol

22509-74-6

N-ethoxycarbonylphthalimide

71964-88-0

ethyl N-<2-(methoxycarbonyl)benzoyl>carbamate

Conditions
ConditionsYield
for 1h; Heating;100%
61-90-5

L-leucine

22509-74-6

N-ethoxycarbonylphthalimide

2419-38-7

N-phthaloyl-(S)-leucine

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; for 2h;100%
With sodium carbonate In water at 20℃; for 2h;100%
With sodium hydrogencarbonate In water for 1h; Ambient temperature;66%
With sodium carbonate In water35%
With sodium carbonate In water at 20℃; for 5h;
71-44-3

Spermine

22509-74-6

N-ethoxycarbonylphthalimide

104435-59-8

1,12-diphthalimido-4,9-diazadodecane

Conditions
ConditionsYield
In chloroform at 20℃; for 1h;100%
In dichloromethane Ambient temperature;86%
In chloroform Ambient temperature;70%
22509-74-6

N-ethoxycarbonylphthalimide

21802-85-7

2-(cyclohexa-1,4-dien-1-yl)ethan-1-amine

73971-98-9

2-(2-Cyclohexa-1,4-dienyl-ethyl)-isoindole-1,3-dione

Conditions
ConditionsYield
In toluene 1) 1h ambient temperature 2) 1h reflux;100%
61-47-2

serotonin creatinine sulfate monohydrate

22509-74-6

N-ethoxycarbonylphthalimide

53157-46-3

N,N-phthalimido-2-(5-hydroxy-1H-indole-3-yl)ethylamine

Conditions
ConditionsYield
With potassium carbonate In water100%
22509-74-6

N-ethoxycarbonylphthalimide

1204659-78-8

5-amino-3',5'-di-O-(tert-butyldimethylsilyl)-4,5-dihydro-2'-deoxyuridine

1204659-80-2

2-{1-[4-(tert-butyldimethylsiloxy)-5-(tert-butyldimethylsiloxymethyl)tetrahydrofuran-2-yl]-2,4-dioxohexahydropyrimidin-5-yl}isoindole-1,3-dione

Conditions
ConditionsYield
In benzene for 12h; Reflux; Inert atmosphere;100%
16338-48-0

L-allylglycine

22509-74-6

N-ethoxycarbonylphthalimide

110658-33-8

(S)-2-(1,3-dioxoisoindolin-2-yl)pent-4-enoic acid

Conditions
ConditionsYield
With sodium carbonate In water at 21 - 24℃; for 3h;99%
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Schlenk technique; Reflux;87%
With sodium carbonate In water for 3h;65%
22509-74-6

N-ethoxycarbonylphthalimide

156-87-6

propan-1-ol-3-amine

883-44-3

N-(3-hydroxypropyl)phthalimide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 6h; Ambient temperature;99%
In chloroform for 2h; Ambient temperature; Yield given;
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Specification

The N-Carbethoxyphthalimide, with the CAS registry number 22509-74-6, is also known as Ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate. It belongs to the product categories of Biochemistry; N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Phthalimides; Peptide Synthesis; Protection & Derivatization Reagents (for Synthesis); Protective Reagents (Peptide Synthesis); Synthetic Organic Chemistry. Its EINECS registry number is 245-048-5. This chemical's molecular formula is C11H9NO4 and molecular weight is 219.19. What's more, its IUPAC name is called Ethyl 1,3-dioxoisoindole-2-carboxylate.

Physical properties about N-Carbethoxyphthalimide are: (1)ACD/LogP: 1.472; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.47; (4)ACD/LogD (pH 7.4): 1.47; (5)ACD/BCF (pH 5.5): 7.74; (6)ACD/BCF (pH 7.4): 7.74; (7)ACD/KOC (pH 5.5): 150.62; (8)ACD/KOC (pH 7.4): 150.62; (9)#H bond acceptors: 5 ; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 63.68 Å2; (13)Index of Refraction: 1.595; (14)Molar Refractivity: 53.226 cm3; (15)Molar Volume: 156.701 cm3; (16)Polarizability: 21.101×10-24cm3; (17)Surface Tension: 59.296 dyne/cm; (18)Density: 1.399 g/cm3; (19)Flash Point: 167.815 °C; (20)Enthalpy of Vaporization: 59.884 kJ/mol; (21)Boiling Point: 353.871 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of N-Carbethoxyphthalimide: this chemical can be prepared by carbonochloridic acid ethyl ester with phthalimide; potassium salt. This reaction needs reagent 18-crown-6 and solvent toluene at temperature of 90 °C. The reaction time is 1 hour. The yield is 96 %.

N-Carbethoxyphthalimide can be prepared by carbonochloridic acid ethyl ester with phthalimide; potassium salt.

Uses of N-Carbethoxyphthalimide: it is used to produce other chemicals. For example, it can react with 2-pyridin-3-yl-ethylamine to get 3-(2-phthalimidoethyl)pyridine. This reaction needs solvent ethanol at temperature of 60 °C. The reaction time is 0.5 hour. The yield is 58 %.

N-Carbethoxyphthalimide can react with 2-pyridin-3-yl-ethylamine to get 3-(2-phthalimidoethyl)pyridine.

When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should avoid contacting with skin, eyes and wear suitable protective clothing, gloves. The gas can not be breathed. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C2c1ccccc1C(=O)N2C(=O)OCC
(2) InChI: 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
(3) InChIKey: VRHAQNTWKSVEEC-UHFFFAOYSA-N