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4-Nitro-N-methylphthalimide

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Name

4-Nitro-N-methylphthalimide

EINECS 255-483-2
CAS No. 41663-84-7 Density 1.533 g/cm3
PSA 83.20000 LogP 1.28170
Solubility N/A Melting Point 94-98 °C(lit.)
Formula C9H6N2O4 Boiling Point 361.1 °C at 760 mmHg
Molecular Weight 206.158 Flash Point 172.2 °C
Transport Information N/A Appearance N/A
Safety 26-36 Risk Codes 36/38
Molecular Structure Molecular Structure of 41663-84-7 (4-Nitro-N-methylphthalimide) Hazard Symbols IrritantXi
Synonyms

Phthalimide,N-methyl-4-nitro- (6CI,7CI);N-Methyl-4-nitrophthalimide;

Article Data 25

4-Nitro-N-methylphthalimide Synthetic route

550-44-7

N-methylphthalimide

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 60℃; for 0.05h; Temperature;96%
With sulfuric acid; nitric acid at 30℃; for 3h; Temperature;94%
With sulfuric acid; potassium nitrate at -5 - 40℃; for 4h; Reagent/catalyst; Temperature;91%
89-40-7

4-nitrophthalimide

74-88-4

methyl iodide

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 5h; Inert atmosphere; Reflux; chemoselective reaction;91%
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 1h;60%
With potassium carbonate; N,N-dimethyl-formamide at 135 - 145℃;
With potassium carbonate In N,N-dimethyl-formamide at 70 - 110℃; Inert atmosphere;
89-40-7

4-nitrophthalimide

616-38-6

carbonic acid dimethyl ester

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In N,N-dimethyl-formamide at 95℃; for 12h;86%
512-56-1

trimethyl phosphite

5330-05-2

4-nitrophthalimide potassium salt

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With N,N-dimethyl-formamide at 125 - 130℃;
5330-05-2

4-nitrophthalimide potassium salt

74-88-4

methyl iodide

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With N,N-dimethyl-formamide at 135 - 145℃;
550-44-7

N-methylphthalimide

A

2593-81-9

N-methyl-3-nitrophthalimide

B

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With nitric acid; Sulfate; zirconium(IV) oxide In tetrachloromethane at 20℃; for 17h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
106-44-5

p-cresol

72709-48-9

Sodium; 2-methylcarbamoyl-4-nitro-benzoate

72709-50-3

Sodium; 2-methylcarbamoyl-5-nitro-benzoate

A

72709-41-2

N-Methyl-4-(4-methylphenoxy)phthalimide

B

27507-54-6

oxo-bis-4,4'-(N-methylphthalimide)

C

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
In dimethyl sulfoxide at 142℃; for 3.5h;
acidic methylamine salt of/the/ 4-nitro-phthalic acid

acidic methylamine salt of/the/ 4-nitro-phthalic acid

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
at 175 - 180℃;
5466-84-2

4-nitrophthalic anhydride

74-89-5

methylamine

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
Stage #1: 4-nitrophthalic anhydride; methylamine In ethanol at 0℃; for 2h;
Stage #2: With acetic anhydride for 0.25h; Reflux;
4.9 g
5466-84-2

4-nitrophthalic anhydride

41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With acetic anhydride; methylamine In ethanol

4-Nitro-N-methylphthalimide Specification

The IUPAC name of 4-Nitro-N-methylphthalimide is 2-methyl-5-nitroisoindole-1,3-dione. With the CAS registry number 41663-84-7, it is also named as 1H-Isoindole-1,3(2H)-dione, 2-methyl-5-nitro-. The product's categories are Miscellaneous; N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Phthalimides. Besides, it should be stored in sealed, cool, dry place. In addition, its molecular formula is C9H6N2O4 and molecular weight is 206.16.

The other characteristics of this product can be summarized as: (1)EINECS: 255-483-2; (2)XLogP3: 1.2; (3)H-Bond Donor: 0; (4)H-Bond Acceptor: 4; (5)Rotatable Bond Count: 0; (6)Exact Mass: 206.032757; (7)MonoIsotopic Mass: 206.032757; (8)Topological Polar Surface Area: 83.2; (9)Heavy Atom Count: 15; (10)Complexity: 336; (11)Melting Point: 94-98 °C; (12)Index of Refraction: 1.647; (13)Molar Refractivity: 48.89 cm3; (14)Molar Volume: 134.4 cm3; (15)Polarizability: 19.38×10-24 cm3; (16)Surface Tension: 68.1 dyne/cm; (17)Density: 1.533 g/cm3; (18)Flash Point: 172.2 °C; (19)Enthalpy of Vaporization: 60.69 kJ/mol; (20)Boiling Point: 361.1 °C at 760 mmHg; (21)Vapour Pressure: 2.12E-05 mmHg at 25 °C.

Preparation of 4-Nitro-N-methylphthalimide: this chemical can be prepared by the reaction of 5-Nitro-isoindole-1,3-dione with Iodomethane.



This reaction needs K2CO3 and Dimethylformamide at temperature of 130 °C. The reaction time is 1 hour. The yield is 60 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: CN1C(=O)C2=C(C1=O)C=C(C=C2)[N+](=O)[O-]
(2)InChI: InChI=1S/C9H6N2O4/c1-10-8(12)6-3-2-5(11(14)15)4-7(6)9(10)13/h2-4H,1H3
(3)InChIKey: JBCHWGTZAAZJKG-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD skin > 2gm/kg (2000mg/kg)   National Technical Information Service. Vol. OTS0540086,
rat LD50 oral 2800mg/kg (2800mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) National Technical Information Service. Vol. OTS0540086,

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