Product Name

  • Name

    N-Carbethoxyphthalimide

  • EINECS 245-048-5
  • CAS No. 22509-74-6
  • Article Data26
  • CAS DataBase
  • Density 1.398 g/cm3
  • Solubility insoluble in water
  • Melting Point 90-92 °C
  • Formula C11H9NO4
  • Boiling Point 353.871 °C at 760 mmHg
  • Molecular Weight 219.197
  • Flash Point 167.815 °C
  • Transport Information
  • Appearance White crystalline powder
  • Safety 22-24/25-36/37/39-26
  • Risk Codes 36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 22509-74-6 (N-Carbethoxyphthalimide)
  • Hazard Symbols HarmfulXn
  • 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;
  • PSA 63.68000
  • LogP 1.37700

Synthetic route

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

potassium phtalimide
1074-82-4

potassium phtalimide

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

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

phthalimide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

N-ethoxycarbonylphthalimide
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%
methanol
67-56-1

methanol

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

ethyl N-<2-(methoxycarbonyl)benzoyl>carbamate
71964-88-0

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

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

L-leucine

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

N-phthaloyl-(S)-leucine
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;
Spermine
71-44-3

Spermine

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

1,12-diphthalimido-4,9-diazadodecane
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%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

2-(cyclohexa-1,4-dien-1-yl)ethan-1-amine
21802-85-7

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

2-(2-Cyclohexa-1,4-dienyl-ethyl)-isoindole-1,3-dione
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%
serotonin creatinine sulfate monohydrate
61-47-2

serotonin creatinine sulfate monohydrate

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

N,N-phthalimido-2-(5-hydroxy-1H-indole-3-yl)ethylamine
53157-46-3

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

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

N-ethoxycarbonylphthalimide

5-amino-3',5'-di-O-(tert-butyldimethylsilyl)-4,5-dihydro-2'-deoxyuridine
1204659-78-8

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

2-{1-[4-(tert-butyldimethylsiloxy)-5-(tert-butyldimethylsiloxymethyl)tetrahydrofuran-2-yl]-2,4-dioxohexahydropyrimidin-5-yl}isoindole-1,3-dione
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%
L-allylglycine
16338-48-0

L-allylglycine

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

(S)-2-(1,3-dioxoisoindolin-2-yl)pent-4-enoic acid
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%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

N-(3-hydroxypropyl)phthalimide
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;
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

(5-amino-pentyl)-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester
200402-41-1

(5-amino-pentyl)-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester

N-(5-((1,1-diethoxyethyl)ethoxyphosphoryl)pentyl)phthalimide
200402-42-2

N-(5-((1,1-diethoxyethyl)ethoxyphosphoryl)pentyl)phthalimide

Conditions
ConditionsYield
With sodium carbonate In dichloromethane at 20℃; for 5h;99%
ethanol
64-17-5

ethanol

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

ethyl N-<2-(ethoxycarbonyl)benzoyl>carbamate
71964-89-1

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

Conditions
ConditionsYield
for 36h; Heating;98%
L-glutamic acid γ-benzyl ester
1676-73-9

L-glutamic acid γ-benzyl ester

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

(2S)-4-benzyloxicarbonyl-2-phthalimidobutanoic acid
88784-33-2

(2S)-4-benzyloxicarbonyl-2-phthalimidobutanoic acid

Conditions
ConditionsYield
With TEA In tetrahydrofuran Heating;98%
With sodium carbonate
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

histamine dichloride
56-92-8

histamine dichloride

2-(2-(1H-imidazol-4-yl)ethyl)isoindoline-1,3-dione
5959-80-8

2-(2-(1H-imidazol-4-yl)ethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; for 2h;98%
With sodium carbonate In water at 20℃; for 2h;
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

L-Tryptophan
73-22-3

L-Tryptophan

N-phthalimide-L-tryptophan
32675-71-1, 48208-26-0, 62361-30-2

N-phthalimide-L-tryptophan

Conditions
ConditionsYield
Stage #1: L-Tryptophan With sodium carbonate In water
Stage #2: N-ethoxycarbonylphthalimide In water at 20℃; for 2h;		98%
With sodium carbonate In water at 20℃; for 1h;95%
With sodium carbonate In water at 20℃; for 5h;
4-aminobutyrylaldehyde diethylacetal
6346-09-4

4-aminobutyrylaldehyde diethylacetal

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

2-(4,4-diethoxybutyl)isoindoline-1,3-dione
32464-55-4

2-(4,4-diethoxybutyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With sodium hydrogencarbonate for 2h; Ambient temperature;97%
With triethylamine In tetrahydrofuran for 6h; Ambient temperature;95%
With triethylamine In tetrahydrofuran at 20℃; for 16h; Cooling with ice;94%
N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

N1,N10-bisphthaloylspermidine
104435-58-7

N1,N10-bisphthaloylspermidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2.5h;96%
In dichloromethane at 25℃; for 2h;90%
In chloroform at 20 - 25℃; for 0.75h;75%
at 20 - 25℃;
In chloroform Acylation;
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

sodium p-aminosalicylate
133-10-8

sodium p-aminosalicylate

2-hydroxy-4-(1,3-dioxoisoindolin-2-yl)benzoic acid
36467-52-4

2-hydroxy-4-(1,3-dioxoisoindolin-2-yl)benzoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate; triethylamine In water at 5℃; for 5h;95.1%
11-aminoundecanoic acid
2432-99-7

11-aminoundecanoic acid

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

11-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-undecanoic acid
4403-42-3

11-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-undecanoic acid

Conditions
ConditionsYield
With sodium carbonate In water for 6h;95%
With sodium carbonate In water at 20℃; for 6h;93%
With sodium carbonate In water at 25℃; for 1h;63%
56%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

1-(2,5-dimethoxy-4-(6-hydroxyhexyl)phenyl)-2-aminopropane
374808-53-4

1-(2,5-dimethoxy-4-(6-hydroxyhexyl)phenyl)-2-aminopropane

6-(2,5-dimethoxy-4-(2-[N,N-phthalimido]propyl)phenyl)hexanol
374808-54-5

6-(2,5-dimethoxy-4-(2-[N,N-phthalimido]propyl)phenyl)hexanol

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 18h;95%
tert-butyl (S)-2-amino-6-hydroxyhexanoate
873581-12-5

tert-butyl (S)-2-amino-6-hydroxyhexanoate

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

C18H23NO5
873581-13-6

C18H23NO5

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2h;95%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2h;
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

(2S,4S)-2-Amino-4-methyl-pentanedioic acid 1-tert-butyl ester
186828-00-2

(2S,4S)-2-Amino-4-methyl-pentanedioic acid 1-tert-butyl ester

(2S,4S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-methyl-pentanedioic acid 1-tert-butyl ester
186828-01-3

(2S,4S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-methyl-pentanedioic acid 1-tert-butyl ester

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water for 18h; Ambient temperature;94%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

3-Phenylpropan-1-amine
2038-57-5

3-Phenylpropan-1-amine

2-(3-phenylpropyl)-1H-isoindole-1,3(2H)-dione
54981-86-1

2-(3-phenylpropyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; water at 20℃;94%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

N-(4-Amino-butyl)-2,2,2-trifluoro-acetamide

N-(4-Amino-butyl)-2,2,2-trifluoro-acetamide

N-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-2,2,2-trifluoro-acetimidic acid
188965-96-0

N-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-2,2,2-trifluoro-acetimidic acid

Conditions
ConditionsYield
With TEA In tetrahydrofuran Heating;93%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

N-(4-Amino-butyl)-2,2,2-trifluoro-acetamide

N-(4-Amino-butyl)-2,2,2-trifluoro-acetamide

N-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-2,2,2-trifluoro-acetamide
188965-96-0

N-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-2,2,2-trifluoro-acetamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 12h; Heating;93%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
2491-18-1

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride

methyl (S)-2-phthalimido-4-methylthiobutanoate
39739-05-4

methyl (S)-2-phthalimido-4-methylthiobutanoate

Conditions
ConditionsYield
With sodium carbonate In chloroform; water at 25℃; for 2h;92%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

trans-(3R,4S)-1-(4-methoxyphenyl)-3-amino-4-<(1'S)-1',2'-O-isopropylideneethyl>-2-azetidinone
141040-22-4

trans-(3R,4S)-1-(4-methoxyphenyl)-3-amino-4-<(1'S)-1',2'-O-isopropylideneethyl>-2-azetidinone

trans-(3R,4S)-1-(4-methoxyphenyl)-3-phthalimido-4-<(1'S)-1',2'-O-isopropylideneethyl>-2-azetidinone
141040-23-5

trans-(3R,4S)-1-(4-methoxyphenyl)-3-phthalimido-4-<(1'S)-1',2'-O-isopropylideneethyl>-2-azetidinone

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water for 1h; Ambient temperature;92%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

trans-3-amino-3-(4-bromophenyl)-1-cyclopropylcyclobutanol
1402603-95-5

trans-3-amino-3-(4-bromophenyl)-1-cyclopropylcyclobutanol

2-(trans-1-(4-bromophenyl)-3-cyclopropyl-3-hydroxycyclobutyl)isoindoline-1,3-dione
1199557-06-6

2-(trans-1-(4-bromophenyl)-3-cyclopropyl-3-hydroxycyclobutyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With triethylamine In chloroform at 70℃; for 38h;92%
With triethylamine In chloroform at 70℃; for 38h;92%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

2-((5,5-dimethyl-1,3,2-dioxaborinan-2-yl)methyl)-N-phenylacrylamide

2-((5,5-dimethyl-1,3,2-dioxaborinan-2-yl)methyl)-N-phenylacrylamide

ethyl 1-hydroxy-3-oxo-1-(2-(phenylcarbamoyl)allyl)isoindoline-2-carboxylate

ethyl 1-hydroxy-3-oxo-1-(2-(phenylcarbamoyl)allyl)isoindoline-2-carboxylate

Conditions
ConditionsYield
With potassium carbonate; zinc dibromide In chloroform at 0 - 20℃; for 12h; Inert atmosphere;92%
With 18-crown-6 ether; potassium carbonate; zinc dibromide In chloroform
methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside
4603-89-8

methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-α-D-glucopyranoside
42775-84-8

methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-α-D-glucopyranoside

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 23℃; for 16h;91%

N-Carbethoxyphthalimide 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

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