| Identification | More | [Name]
O-Phthalimide | [CAS]
85-41-6 | [Synonyms]
1,2-BENZENEDICARBOXIMIDE
1,2-PHTHALIC IMIDE
1,3-DIHYDROISOINDOLE-1,3-DIONE
1,3-ISOINDOLEDIONE
1H-ISOINDOLE-1,3(2H)-DIONE
ISOINDOLE-1,3-DIONE
LABOTEST-BB LTBB000782
O-PHTHALIC IMIDE
o-Phthalimide
Phenylimide
PHTHALIC ACID IMIDE
phthalic dicarboximide
PHTHALIMIDE
1,3-Isoindolinedione
2-Diazoindan-1,3-dione
Benzoimide
Ftalimmide
Phthalimid
PHTHALYLIMIDE
2,5-Isoindoledione | [EINECS(EC#)]
201-603-3 | [Molecular Formula]
C12H8N2O6 | [MDL Number]
MFCD08448696 | [Molecular Weight]
276.2 | [MOL File]
85-41-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to slightly yellowish crystalline flakes | [Melting point ]
232-235 °C(lit.)
| [Boiling point ]
366 °C
| [density ]
1.21 | [vapor pressure ]
0.001Pa at 25℃ | [refractive index ]
1.4700 (estimate) | [Fp ]
165 °C
| [storage temp. ]
Store below +30°C. | [solubility ]
water: slightly soluble(lit.) | [form ]
Crystalline Flakes | [pka]
8.3(at 25℃) | [color ]
White to slightly yellow | [PH]
3.8 (0.6g/l, H2O) | [Water Solubility ]
<0.1 g/100 mL at 19.5 ºC | [Merck ]
14,7373 | [Sublimation ]
366 ºC | [BRN ]
118522 | [Henry's Law Constant]
9.9×102 mol/(m3Pa) at 25℃, HSDB (2015) | [InChI]
1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)8(11)9-7/h1-4H,(H,9,10,11) | [InChIKey]
XKJCHHZQLQNZHY-UHFFFAOYSA-N | [SMILES]
O=C1NC(=O)c2ccccc12 | [LogP]
1.15 | [CAS DataBase Reference]
85-41-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Phthalimide(85-41-6) | [EPA Substance Registry System]
85-41-6(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H319-H335-H315 | [Precautionary statements ]
P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
1
| [RTECS ]
TI3920000
| [Autoignition Temperature]
>500 °C | [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29251995 | [Storage Class]
13 - Non Combustible Solids | [Safety Profile]
Moderately toxic by
intraperitoneal route. Mildly toxic by
ingestion. An experimental teratogen. Other
experimental reproductive effects. When
heated to decomposition it emits toxic
fumes of NOx. | [Hazardous Substances Data]
85-41-6(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit > 7940 mg/kg |
| Hazard Information | Back Directory | [General Description]
White to light tan powder. Slightly acidic. | [Reactivity Profile]
PHTHALIMIDE(85-41-6) is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). This chemical forms salts with bases. | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. | [Fire Hazard]
Literature sources indicate that this compound is combustible. | [Chemical Properties]
white to slightly yellowish crystalline flakes | [Uses]
Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. Phthalimide analogues have been extensively used in medicinal chemistry owing to their wide spectrum
of applications as anti-convulsant, anti-inflammatory, analgesic, hypolipidimic and immunomodulatory activities. | [Uses]
Phthalimide, C6H4(CO)2NH, is an imide of commercial and industrial importance, forming a number of interesting derivatives. With alcoholic potash, phthalimide forms a potassium derivative, C6H4 (CO)2 NK, which, when reacted with ethyl iodide (or other alkyl halides), yields ethylphthalimide, C6H4(CO)2 N C2H5. The latter product, when hydrolyzed with an acid or alkali, further yields ethylamine [CAS: 75-04-7] C2H7N. Such reaction chains are useful in the preparation of certain primary amines and their derivatives. | [Definition]
ChEBI: A dicarboximide that is 2,3-dihydro-1H-isoindole substituted by oxo groups at positions 1 and 3. | [Reactions]
The hydrogen atom on the nitrogen of phthalimide exhibits acidic properties and reacts with a base to form a salt. Exploiting the strong nucleophilicity of the nitrogen anion, this salt is then reacted with a halogenated hydrocarbon to yield an N-alkylphthalimide, which is subsequently hydrolyzed with acid or with hydrazine to produce a high-purity primary amine. This reaction is known as the Gabriel reaction.
 | [Synthesis Reference(s)]
Journal of the American Chemical Society, 111, p. 3725, 1989 DOI: 10.1021/ja00192a034
The Journal of Organic Chemistry, 45, p. 363, 1980 DOI: 10.1021/jo01290a038
Tetrahedron Letters, 34, p. 6907, 1993 DOI: 10.1016/S0040-4039(00)91827-6 | [Purification Methods]
Crystallise the imide from EtOH (20mL/g) (charcoal), or sublime it. For potassium phthalimide see entry in “Metal-organic Compounds”, Chapter 5. [Beilstein 21/10 V 270.] | [References]
[1] Ohno, H., and, Takami, Y., and, & and Kazuya Kanemoto*. (2026). Preparation of Unsymmetrical Disulfides via Catalytic Lewis Base Activation of N-(Organodithio)phthalimides. Journal of Organic Chemistry, 91 4, 1817–1822. https://doi.org/10.1021/acs.joc.5c03056
[2] Li, J., Zheng, Q., & Dömling*, A. (2024). Exploring Phthalimide as the Acid Component in the Passerini Reaction. Organic Letters, 26 4, 829–833. https://doi.org/10.1021/acs.orglett.3c03962 |
|
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