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| CAS No.: | 550-44-7 |
|---|---|
| Name: | N-Methylphthalimide |
| Article Data: | 169 |
| Molecular Structure: | |
|
|
|
| Formula: | C9H7NO2 |
| Molecular Weight: | 161.16 |
| Synonyms: | 1H-Isoindole-1,3(2H)-dione, 2-methyl-;5-21-10-00273 (Beilstein Handbook Reference);1H-Isoindole-1, 3 (2H)-dione, 2-methyl-;Phthalimide, N-methyl-;2-Methyl-isoindole-1,3-dione; |
| EINECS: | 208-982-4 |
| Density: | 1.314 g/cm3 |
| Melting Point: | 129-132 °C(lit.) |
| Boiling Point: | 286 °C at 760 mmHg |
| Flash Point: | 117.4 °C |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 37.38000 |
| LogP: | 0.85030 |
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| Conditions | Yield |
|---|---|
| With bis-(2-(1-adamantyl)ethyl) azodicarboxylate; triphenylphosphine Mitsunobu reaction; | 100% |
| With bis(3-(perfluoro-t-butyloxy)propyl)diazodicarboxylate; bis-phenyl-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; Inert atmosphere; | 95% |
| With PhP(C6H4-p-(CH2)2C6F13)2; diethylazodicarboxylate In tetrahydrofuran | 91% |
- 19532-98-0
N1,N2-dimethylphthalamide
- 550-44-7
N-methylphthalimide
| Conditions | Yield |
|---|---|
| With hydrogenchloride at 20℃; under 750.06 Torr; Cyclization; solid-gas reaction; | 100% |
| With water | |
| at 190℃; | |
| at 190℃; |
| Conditions | Yield |
|---|---|
| With sodium methylate; sodium hydride In dimethyl sulfoxide at 20℃; for 10h; | 100% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; hydrogen In water at 75 - 80℃; pH=5.5; Temperature; Concentration; Autoclave; Inert atmosphere; | 99.33% |
| at 150 - 160℃; |
| Conditions | Yield |
|---|---|
| In water at 120 - 180℃; for 0.333333h; Autoclave; Inert atmosphere; | 99% |
| In ethanol; toluene for 3h; Solvent; Reflux; | 95% |
| In water | 91% |
| Conditions | Yield |
|---|---|
| With acrylonitrile; β‐cyclodextrin In acetonitrile UV-irradiation; Inert atmosphere; | 97% |
| With potassium carbonate In water; acetone at 15℃; Irradiation; | 95% |
| In acetonitrile for 1h; Kinetics; Mechanism; Irradiation; Variation of solvents, irradiation times and methods.; | 94% |
| Conditions | Yield |
|---|---|
| With N,N,N,N,-tetramethylethylenediamine In N,N-dimethyl-formamide at 95℃; for 8h; | 95% |
| Conditions | Yield |
|---|---|
| With triethylamine In toluene at 100℃; under 760.051 Torr; for 4h; Autoclave; | 95% |
| Conditions | Yield |
|---|---|
| With iodine; palladium diacetate; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; | 95% |
| Conditions | Yield |
|---|---|
| With potassium dihydrogenphosphate; Cp*Rh(MeCN)3[ClO4]2; silver carbonate In tert-Amyl alcohol at 100℃; under 760.051 Torr; for 24h; | 94% |
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Consensus Reports
Reported in EPA TSCA Inventory.
Specification
The N-Methylphthalimide is an organic compound with the formula C9H7NO2. The IUPAC name of this chemical is 2-methylisoindole-1,3-dione. With the CAS registry number 550-44-7, it is also named as 1H-Isoindole-1,3(2H)-dione, 2-methyl-. The product's categories are API Intermediates; N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Phthalimides; Cyclic ImidesDerivatization Reagents; Carbonyl Compounds; Derivatization Reagents HPLC; Organic Building Blocks; UV-VIS. Besides, it should be stored in a cool and well-ventilated place.
Physical properties about N-Methylphthalimide are: (1)ACD/LogP: 1.56; (2)ACD/LogD (pH 5.5): 1.56; (3)ACD/LogD (pH 7.4): 1.56; (4)ACD/BCF (pH 5.5): 8.96; (5)ACD/BCF (pH 7.4): 8.96; (6)ACD/KOC (pH 5.5): 167.26; (7)ACD/KOC (pH 7.4): 167.26; (8)#H bond acceptors: 3; (9)Polar Surface Area: 37.38 Å2; (10)Index of Refraction: 1.607; (11)Molar Refractivity: 42.35 cm3; (12)Molar Volume: 122.5 cm3; (13)Polarizability: 16.78×10-24cm3; (14)Surface Tension: 52 dyne/cm; (15)Density: 1.314 g/cm3; (16)Flash Point: 117.4 °C; (17)Enthalpy of Vaporization: 52.51 kJ/mol; (18)Boiling Point: 286 °C at 760 mmHg; (19)Vapour Pressure: 0.00271 mmHg at 25°C.
Preparation: this chemical can be prepared by phthalimide and methanol. This reaction will need reagent PhP(C6H4-p-(CH2)2C6F13)2, DEAD and solvent tetrahydrofuran. The yield is about 91%.
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Uses of N-Methylphthalimide: it can be used to produce N-bromomethyl-phthalimide at temperature of 160 - 170 °C. It will need reagent bromine.
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When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, 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
(2)InChI: InChI=1/C9H7NO2/c1-10-8(11)6-4-2-3-5-7(6)9(10)12/h2-5H,1H3
(3)InChIKey: ZXLYYQUMYFHCLQ-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C9H7NO2/c1-10-8(11)6-4-2-3-5-7(6)9(10)12/h2-5H,1H3
(5)Std. InChIKey: ZXLYYQUMYFHCLQ-UHFFFAOYSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| rat | LD | oral | > 500mg/kg (500mg/kg) | National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 23, 1953. |