?????
|
|
????? ??
- ???
- 232-235 °C(lit.)
- ?? ?
- 366 °C
- ??
- 1.21
- ???
- 0.001Pa at 25℃
- ???
- 1.4700 (estimate)
- ???
- 165 °C
- ?? ??
- Store below +30°C.
- ???
- ?: ?? ???(lit.)
- ?? ?? (pKa)
- 8.3(at 25℃)
- ??? ??
- ???? ????
- ??
- ???? ?? ???
- ??????(pH)
- 3.8 (0.6g/l, H2O)
- ???
- 19.5&C?? <0.1g/100mL
- ???
- 366 ºC
- Merck
- 14,7373
- 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 ??????
- 85-41-6(CAS DataBase Reference)
- NIST
- Phthalimide(85-41-6)
??
- ?? ? ?? ??
- ?? ? ???? ?? (GHS)
| ?? ???? ?? | 20/21/22-36/37/38-40 | ||
|---|---|---|---|
| ????? | 22-24/25 | ||
| WGK ?? | 1 | ||
| RTECS ?? | TI3920000 | ||
| ?? ?? ?? | >500 °C | ||
| TSCA | TSCA listed | ||
| HS ?? | 29251995 | ||
| ???? ??? | 13 - Non Combustible Solids | ||
| ?? ?? ??? | 85-41-6(Hazardous Substances Data) | ||
| ?? | LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit > 7940 mg/kg | ||
| ???? ?? | KE-21523 |
????? C??? ??, ??, ??
??
???? ???????? ??????? ????? N-?????? ???, ? ????? ?? ????? ???? ??? ??? ??????? ?? ????.??? ??
white to slightly yellowish crystalline flakes??
ChEBI: Phthalimide is a dicarboximide that is 2,3-dihydro-1H-isoindole substituted by oxo groups at positions 1 and 3.?? ??
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.
?? ??
White to light tan powder. Slightly acidic.??? ?? ??
Insoluble in water.?? ???
O-Phthalimide 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). O-Phthalimide forms salts with bases.????
ACUTE/CHRONIC HAZARDS: When heated to decomposition O-Phthalimide emits toxic fumes of nitrogen oxides.????
Literature sources indicate that O-Phthalimide is combustible.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.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.]?? ??
[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., & D?mling*, 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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?? ??
?????
N-(Hydroxymethyl)phthalimide
1-(1H-pyrazol-1-yl)propan-2-amine
Fmoc-8-amino-3,6-dioxaoctanoic acid
1,2-??????????
C-(3,4-DIHYDRO-2H-BENZO[1,4]OXAZIN-3-YL)-????
????
4-Nitrophthalimide
N-(Chloromethyl)phthalimide
??
N-(2-[4-(4-CHLOROPHENYL)PIPERAZIN-1-YL]ETHYL)-3-METHOXYBENZAMIDE
????
(Aminomethyl)phosphonic acid
???????
2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione
N-????????????
???
Ofloxacin
2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE
2-(?????)???
??
5-????????
1,4-??????
2-(3-BROMO-1-METHYL-2-OXOPROPYL)-L H-ISINDOLE-1,3-(2H)-DIONE
5-[(1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)METHYL]-2-FURALDEHYDE
2-(?????????)-1H-?????-1,3(2H)-???
????? ?? ??
???( 559)?? ??
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