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| CAS No.: | 524-38-9 |
|---|---|
| Name: | N-Hydroxyphthalimide |
| Molecular Structure: | |
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|
|
| Formula: | C8H5NO3 |
| Molecular Weight: | 163.133 |
| Synonyms: | Phthalimide,N-hydroxy- (6CI,7CI,8CI);2-Hydroxy-1H-isoindole-1,3(2H)-dione;2-Hydroxyisoindole-1,3-dione;2-Hydroxyphthalimide;F 802;NSC 770; |
| EINECS: | 208-358-1 |
| Density: | 1.638 g/cm3 |
| Melting Point: | 233 °C (dec.)(lit.) |
| Boiling Point: | 370.3 °C at 760 mmHg |
| Flash Point: | 177.8 °C |
| Solubility: | slightly soluble in the water |
| Appearance: | yellow moist powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36-37/39 |
| PSA: | 57.61000 |
| LogP: | 0.60970 |
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- 1582289-49-3
3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione
- 524-38-9
N-hydroxyphthalimide
| Conditions | Yield |
|---|---|
| at 130℃; for 3h; Inert atmosphere; | 99% |
- 17720-64-8
N-acetoxyphthalimide
- 524-38-9
N-hydroxyphthalimide
| Conditions | Yield |
|---|---|
| With methanol; potassium permanganate at 25℃; chemoselective reaction; | 96% |
| Conditions | Yield |
|---|---|
| With pyridine; hydroxylamine hydrochloride; acetic anhydride for 4h; Heating; | 95% |
| With hydroxylamine hydrochloride; triethylamine In isopropyl alcohol at 95℃; for 0.7h; Reagent/catalyst; Temperature; | 94.6% |
| With hydroxyammonium sulfate; sodium hydroxide In water at 90℃; Product distribution / selectivity; | 89.7% |
- 150220-29-4
tert-butyl 1,3-dioxoisoindoline-2-carboxylate
- 524-38-9
N-hydroxyphthalimide
| Conditions | Yield |
|---|---|
| With hydroxylamine In acetonitrile at 20℃; | 95% |
- 1582289-49-3
3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione
A
- 524-38-9
N-hydroxyphthalimide
B
- 31583-39-8
3H-benzo[d][1,2]oxazine-1,4-dione
| Conditions | Yield |
|---|---|
| In water; acetonitrile for 1h; Time; Reflux; | A 7% B 93% |
- 98-82-8
Isopropylbenzene
- 1313016-88-4
ethyl 2-(((1,3-dioxoisoindolin-2-yl)oxy)methyl)acrylate
A
- 524-38-9
N-hydroxyphthalimide
| Conditions | Yield |
|---|---|
| With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 24h; | A n/a B 91% |
- 100-41-4
ethylbenzene
- 1608461-37-5
2-((2-phenylallyl)oxy)isoindoline-1,3-dione
A
- 524-38-9
N-hydroxyphthalimide
B
- 38212-18-9
pent-1-ene-2,4-diyldibenzene
| Conditions | Yield |
|---|---|
| With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 29h; | A n/a B 89% |
- 92856-14-9
2-phenethoxyisoindoline-1,3-dione
- 71-43-2
benzene
A
- 524-38-9
N-hydroxyphthalimide
B
- 103-29-7
1,1'-(1,2-ethanediyl)bisbenzene
| Conditions | Yield |
|---|---|
| With aluminium trichloride for 0.5h; Ambient temperature; | A 76% B 86% |
- 100-41-4
ethylbenzene
- 1313016-88-4
ethyl 2-(((1,3-dioxoisoindolin-2-yl)oxy)methyl)acrylate
A
- 524-38-9
N-hydroxyphthalimide
| Conditions | Yield |
|---|---|
| With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 17h; | A n/a B 85% |
- 58585-84-5
1,3-dioxoisoindolin-2-yl benzoate
- 71-43-2
benzene
A
- 119-61-9
benzophenone
B
- 524-38-9
N-hydroxyphthalimide
| Conditions | Yield |
|---|---|
| With aluminium trichloride for 0.5h; Ambient temperature; | A 81% B 74% |
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Consensus Reports
Specification
The IUPAC name of N-Hydroxyphthalimide is 2-hydroxyisoindole-1,3-dione. With the CAS registry number 524-38-9, it is also named as 1H-Isoindole-1,3(2H)-dione, 2-hydroxy-. The product's categories are biochemistry; carbon radical producing catalysts (environmentally-friendly oxidation); condensation & active esterification; coupling reactions (peptide synthesis); n-substituted maleimides, succinimides & phthalimides; peptide synthesis; synthetic organic chemistry; active esters/additives. It is yellow moist powder which is slightly soluble in the water. When heated to decomposition it emits toxic vapors of NOx. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.32; (4)ACD/LogD (pH 7.4): -0.9; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 32.24; (8)ACD/KOC (pH 7.4): 1.93; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Molar Volume: 99.5 cm3; (13)Polarizability: 15.55×10-24 cm3; (14)Surface Tension: 89.3 dyne/cm; (15)Flash Point: 177.8 °C; (16)Enthalpy of Vaporization: 65.12 kJ/mol; (17)Boiling Point: 370.3 °C at 760 mmHg; (18)Vapour Pressure: 3.87E-06 mmHg at 25°C; (19)Exact Mass: 163.026943; (20)MonoIsotopic Mass: 163.026943; (21)Topological Polar Surface Area: 57.6; (22)Heavy Atom Count: 12; (23)Complexity: 215.
Preparation of N-Hydroxyphthalimide: It can be obtained by phthalic acid anhydride with the reagents sodium carbonate, water and hydroxylamine hydrochloride.
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Uses of N-Hydroxyphthalimide: It is used as intermediate of drugs such as amikacin. And it is also used as alkyl oxidant, catalyst and mineral collector. Additionally, it can react with 2-pyridin-2-yl-ethanol to get 2-(2-pyridin-2-yl-ethoxy)-isoindole-1,3-dione. This reaction needs reagent diethyl azodicarboxylate and PPh3 and solvent CHCl3 at ambient temperature. The reaction time is 1 hours. The yield is 75.5%.
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When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C2c1ccccc1C(=O)N2O
2. InChI:InChI=1/C8H5NO3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4,12H
3. InChIKey:CFMZSMGAMPBRBE-UHFFFAOYAR
The following are the toxicity data which has been tested.
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 178mg/kg (178mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00747, |