4-Nitro-N-methylphthalimide supplier

Name
4-Nitro-N-methylphthalimide
EINECS 255-483-2
CAS No. 41663-84-7
Article Data25
CAS DataBase
Density 1.533 g/cm³
Solubility
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
Appearance
Safety 26-36
Risk Codes 36/38
Molecular Structure
Hazard Symbols Xi
Synonyms Phthalimide,N-methyl-4-nitro- (6CI,7CI);N-Methyl-4-nitrophthalimide;
PSA 83.20000
LogP 1.28170

Synthetic route

: 550-44-7
N-methylphthalimide

: 41663-84-7
4-nitro-N-methyl-phthalimide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In dimethyl sulfoxide at 142℃; for 3.5h;

...Expand

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

Conditions	Yield
at 175 - 180℃;

: 5466-84-2
4-nitrophthalic anhydride

: 74-89-5
methylamine

: 41663-84-7
4-nitro-N-methyl-phthalimide

Conditions

Conditions	Yield
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

Conditions	Yield
With acetic anhydride; methylamine In ethanol

: 136918-14-4
phthalimide

: 41663-84-7
4-nitro-N-methyl-phthalimide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: nitric acid; sulfuric acid / 16 h / 5 - 20 °C 2.1: potassium hydroxide / methanol; ethanol / 3 h / 20 °C 2.2: 1 h / Reflux View Scheme

: 89-40-7
4-nitrophthalimide

halomethane: halomethane

: 41663-84-7
4-nitro-N-methyl-phthalimide

Conditions

Conditions	Yield
Stage #1: 4-nitrophthalimide With potassium hydroxide In methanol; ethanol at 20℃; for 3h; Stage #2: halomethane With potassium carbonate In N,N-dimethyl-formamide for 1h; Reflux;

: 10133-88-7
2-(4-nitrophthalimido)acetic acid

: 41663-84-7
4-nitro-N-methyl-phthalimide

Conditions

Conditions	Yield
Irradiation;

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 139-02-6
sodium phenoxide

: 63197-24-0
4-phenoxy-N-methyl phthalimide

Conditions

Conditions	Yield
N-neopentyl chloride of 4-dibutylaminopyridine In toluene at 110℃; for 1h;	99%
In dimethyl sulfoxide at 15 - 120℃; for 24h; Inert atmosphere;	93%

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 27507-54-6
oxo-bis-4,4'-(N-methylphthalimide)

Conditions

Conditions	Yield
With KF/Al2O3 catalyst In N,N-dimethyl-formamide; toluene at 150 - 160℃; for 6h; Time;	98.7%
With KF/Al2O3 In N,N-dimethyl-formamide; toluene for 8h; Reflux;	82.8%
Stage #1: 4-nitro-N-methyl-phthalimide With potassium acetate In N,N-dimethyl-formamide at 80℃; Stage #2: With water for 0.5h; Reagent/catalyst; Solvent; Reflux;

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 108-46-3
recorcinol

: C24H16N2O6

Conditions

Conditions	Yield
Stage #1: recorcinol With potassium hydroxide In o-xylene at 100℃; for 2h; Inert atmosphere; Reflux; Stage #2: 4-nitro-N-methyl-phthalimide With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In o-xylene at 143℃; for 6h; Reagent/catalyst; Inert atmosphere;	97.2%

: 80-05-7
BPA

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 54395-52-7
4,4’-bisphenol A-bis-N-methylphthalimide

Conditions

Conditions	Yield
Stage #1: BPA With potassium hydroxide In o-xylene at 100℃; for 2h; Inert atmosphere; Reflux; Stage #2: 4-nitro-N-methyl-phthalimide With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In o-xylene at 143℃; for 8h; Reagent/catalyst; Inert atmosphere;	95.8%
Stage #1: BPA With sodium hydroxide In o-xylene at 100 - 143℃; for 4h; Inert atmosphere; Stage #2: 4-nitro-N-methyl-phthalimide In N,N-dimethyl acetamide at 20 - 150℃; for 3h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;	93.8%
Stage #1: BPA With potassium hydroxide In toluene at 80℃; for 3h; Inert atmosphere; Stage #2: 4-nitro-N-methyl-phthalimide With N,N-dimethyl acetamide In N,N-dimethyl-formamide at 140℃; for 5h; Reagent/catalyst; Temperature; Solvent;	91.9%
Stage #1: 4-nitro-N-methyl-phthalimide With sodium hydroxide In water; toluene at 95℃; Dean-Stark; Inert atmosphere; Stage #2: BPA With N-[bis(diethylamino)methylene]-N-ethylethane ammonium chloride; 3,5-dinitro-4-hydroxy-N-methyl phthalimide; sodium chloride In water; toluene at 130℃; Inert atmosphere; Dean-Stark;
With potassium carbonate In N,N-dimethyl-formamide; toluene for 6h; Reflux;

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 2307-00-8
4-amino-N-methylphthalimide

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3h;	95%
With hydrogenchloride; water; tin(ll) chloride at 20℃;	73.2%
With hydrogenchloride; tin(II) chloride dihdyrate In water for 2h;	54.7%

: 41663-84-7
4-nitro-N-methyl-phthalimide

: phenol potassium fluoride

: 63197-24-0
4-phenoxy-N-methyl phthalimide

Conditions

Conditions	Yield
In dimethyl sulfoxide at 15 - 120℃; for 24h; Solvent; Inert atmosphere;	95%

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 108-95-2
phenol

: 63197-24-0
4-phenoxy-N-methyl phthalimide

Conditions

Conditions	Yield
Stage #1: phenol With sodium hydroxide In toluene for 1h; Reflux; Stage #2: 4-nitro-N-methyl-phthalimide In dimethyl sulfoxide at 60℃; for 6h;	95%

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 80-09-1
4,4'-sulfonediphenol

: C30H20N2O8S

Conditions

Conditions	Yield
Stage #1: 4,4'-sulfonediphenol With potassium hydroxide In toluene at 100℃; for 2h; Inert atmosphere; Reflux; Stage #2: 4-nitro-N-methyl-phthalimide With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In toluene at 110℃; for 6h; Inert atmosphere;	94.2%
With potassium carbonate In N,N-dimethyl acetamide; toluene for 6h; Reflux;

: 80-05-7
BPA

: 41663-84-7
4-nitro-N-methyl-phthalimide

: N-methyl-N′-methyl-3,3′,4,4′-bisphenol A diether bisphthalimide

Conditions

Conditions	Yield
Stage #1: BPA With sodium hydroxide In o-xylene at 144℃; for 4h; Inert atmosphere; Stage #2: 4-nitro-N-methyl-phthalimide In N,N-dimethyl acetamide at 155℃; for 6h;	94.2%

: 4112-65-6
5-hydroxy-2-methylisoindoline-1,3-dione

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 27507-54-6
oxo-bis-4,4'-(N-methylphthalimide)

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; toluene Reflux;	90.8%

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 99-96-7
4-hydroxy-benzoic acid

: 4-((N-methylphthalimide)-4-oxy)benzoic acid

Conditions

Conditions	Yield
Stage #1: 4-hydroxy-benzoic acid In dimethyl sulfoxide; toluene at 140 - 160℃; Stage #2: 4-nitro-N-methyl-phthalimide In dimethyl sulfoxide; toluene at 120℃; for 6h;	88%

: hexaethyl guanidinium chloride

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 27507-54-6
oxo-bis-4,4'-(N-methylphthalimide)

Conditions

Conditions	Yield
With potassium acetate	71%

SnCl2 dihydrate: SnCl2 dihydrate

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 2307-00-8
4-amino-N-methylphthalimide

Conditions

Conditions	Yield
In water	54.7%

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 100-59-4
phenylmagnesium chloride

: 4636-67-3
5-anilino-2-methyl-isoindole-1,3-dione

Conditions

Conditions	Yield
Stage #1: 4-nitro-N-methyl-phthalimide; phenylmagnesium chloride In tetrahydrofuran at -50℃; for 2h; Stage #2: With sodium tetrahydroborate; iron(II) chloride In tetrahydrofuran; ethanol; N,N-dimethyl-formamide at 20℃;	26%

: 106-44-5
p-cresol

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 72709-41-2
N-Methyl-4-(4-methylphenoxy)phthalimide

Conditions

Conditions	Yield
With sodium hydroxide 1.) Toluene, Me2SO, 2.) Me2SO, 65-70 deg C, 2 h; Yield given. Multistep reaction;

: 106-44-5
p-cresol

: 41663-84-7
4-nitro-N-methyl-phthalimide

A: 72709-41-2
N-Methyl-4-(4-methylphenoxy)phthalimide

B: 63196-15-6
4-(4-Methylphenoxy)phthalic acid

C: 72709-47-8
N-Methyl-4-nitro-phthalamic acid

D: 72709-49-0
N-Methyl-5-nitro-phthalamic acid

E: 72709-44-5
N-Methyl-5-(4-methylphenoxy)phthalamic acid

F: 72709-42-3
N-Methyl-4-(4-methylphenoxy)phthalamic acid

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 142℃; for 20h; Mechanism; Product distribution; Product distributions at other times, different ratios of rectants, presence of molecular sieves;	A 0.0070 mol B n/a C n/a D n/a E n/a F n/a

...Expand

: 41663-84-7
4-nitro-N-methyl-phthalimide

A: 72709-47-8
N-Methyl-4-nitro-phthalamic acid

B: 72709-49-0
N-Methyl-5-nitro-phthalamic acid

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 142℃; for 1.25h; Mechanism;

: 7647-01-0
hydrogenchloride

: 41663-84-7
4-nitro-N-methyl-phthalimide

tin dichloride: tin dichloride

<4-amino-phthalic acid >-methylimide: <4-amino-phthalic acid >-methylimide

...Expand

: 41663-84-7
4-nitro-N-methyl-phthalimide

: 91289-90-6
4-(2-Amino-1-naphthyldiazenyl)-N-methylnaphthylamid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) SnCl2, HCl, 2.) H2O 2: 1.) NaNO2, HCl, 2.) 1 N NaOH / 2.) ice cooling View Scheme

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^-24cm³; (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,

Product Name

4-Nitro-N-methylphthalimide

Synthetic route

4-Nitro-N-methylphthalimide Specification

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