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524-38-9

Basic Information
CAS No.: 524-38-9
Name: N-Hydroxyphthalimide
Article Data: 78
Molecular Structure:
Molecular Structure of 524-38-9 (N-Hydroxyphthalimide)
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: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
PSA: 57.61000
LogP: 0.60970
Synthetic route
1582289-49-3

3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione

524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
at 130℃; for 3h; Inert atmosphere;99%
17720-64-8

N-acetoxyphthalimide

524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With methanol; potassium permanganate at 25℃; chemoselective reaction;96%
85-44-9

phthalic anhydride

524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

B

ethyl 4-methyl-2-methylene-4-phenylpentanoate

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

B

ethyl 2-methylene-4-phenylpentanoate

Conditions
ConditionsYield
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
ConditionsYield
With aluminium trichloride for 0.5h; Ambient temperature;A 81%
B 74%
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    Formula:C8H5NO3 Molecular Weight:163.14 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

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Consensus Reports

Reported in EPA TSCA Inventory.

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.

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%.

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,