41663-84-7

Basic information

• Product Name: 4-Nitro-N-methylphthalimide
• Synonyms: 2-METHYL-5-NITRO-1H-ISOINDOLE-1,3(2H)DIONE;4-NITRO-N-METHYLPHTHALIMIDE;N-METHYL-4-NITROPHTHALIMIDE;2-methyl-5-nitro-1h-isoindole-3(2h)-dione;ai3-28673;Methylnitrophthalimide;4-NITRO-N-METHTYLPHTHALIMIDE;N-METHY-4-NITRO PHTHALAMIDE
• CAS NO: 41663-84-7
• Molecular Formula: C₉H₆N₂O₄
• Molecular Weight: 206.15
• EINECS: 255-483-2
• Product Categories: Miscellaneous;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides
• Mol File: 41663-84-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 94-98 °C(lit.)
• Boiling Point: 361.1 °C at 760 mmHg
• Flash Point: 172.2 °C
• Appearance: /
• Density: 1.533 g/cm³
• Vapor Pressure: 2.12E-05mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -3.51±0.20(Predicted)
• CAS DataBase Reference: 4-Nitro-N-methylphthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitro-N-methylphthalimide(41663-84-7)
• EPA Substance Registry System: 4-Nitro-N-methylphthalimide(41663-84-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36
• RTECS: NR3398541
• Hazardous Substances Data: 41663-84-7(Hazardous Substances Data)

Usage

Uses

2-Methyl-5-nitro-1H-isoindole-1,3(2H)-dione is a nitroaromatic compound that is toxic to bacteria, cells, animals, humans and their environment.

Hazard

Moderately toxic by ingestion and skin contact. A mild skin irritant.

InChI:InChI=1/C9H6N2O4/c1-10-8(12)6-3-2-5(11(14)15)4-7(6)9(10)13/h2-4H,1H3

Synthetic route

N-methylphthalimide (550-44-7) → 4-nitro-N-methyl-phthalimide (41663-84-7)

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%

4-nitrophthalimide (89-40-7) + methyl iodide (74-88-4) → 4-nitro-N-methyl-phthalimide (41663-84-7)

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;

4-nitrophthalimide (89-40-7) + carbonic acid dimethyl ester (616-38-6) → 4-nitro-N-methyl-phthalimide (41663-84-7)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In N,N-dimethyl-formamide at 95℃; for 12h;	86%

trimethyl phosphite (512-56-1) + 4-nitrophthalimide potassium salt (5330-05-2) → 4-nitro-N-methyl-phthalimide (41663-84-7)

Conditions	Yield
With N,N-dimethyl-formamide at 125 - 130℃;

4-nitrophthalimide potassium salt (5330-05-2) + methyl iodide (74-88-4) → 4-nitro-N-methyl-phthalimide (41663-84-7)

Conditions	Yield
With N,N-dimethyl-formamide at 135 - 145℃;

N-methylphthalimide (550-44-7) → N-methyl-3-nitrophthalimide (2593-81-9) + 4-nitro-N-methyl-phthalimide (41663-84-7)

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;

p-cresol (106-44-5) + Sodium; 2-methylcarbamoyl-4-nitro-benzoate (72709-48-9) + Sodium; 2-methylcarbamoyl-5-nitro-benzoate (72709-50-3) → N-Methyl-4-(4-methylphenoxy)phthalimide (72709-41-2) + oxo-bis-4,4'-(N-methylphthalimide) (27507-54-6) + 4-nitro-N-methyl-phthalimide (41663-84-7)

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

acidic methylamine salt of/the/ 4-nitro-phthalic acid → 4-nitro-N-methyl-phthalimide (41663-84-7)

Conditions	Yield
at 175 - 180℃;

4-nitrophthalic anhydride (5466-84-2) + methylamine (74-89-5) → 4-nitro-N-methyl-phthalimide (41663-84-7)

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

4-nitrophthalic anhydride (5466-84-2) → 4-nitro-N-methyl-phthalimide (41663-84-7)

Conditions	Yield
With acetic anhydride; methylamine In ethanol

phthalimide (136918-14-4) → 4-nitro-N-methyl-phthalimide (41663-84-7)

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

4-nitrophthalimide (89-40-7) + halomethane → 4-nitro-N-methyl-phthalimide (41663-84-7)

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;

2-(4-nitrophthalimido)acetic acid (10133-88-7) → 4-nitro-N-methyl-phthalimide (41663-84-7)

Conditions	Yield
Irradiation;

4-nitro-N-methyl-phthalimide (41663-84-7) + sodium phenoxide (139-02-6) → 4-phenoxy-N-methyl phthalimide (63197-24-0)

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%

4-nitro-N-methyl-phthalimide (41663-84-7) → oxo-bis-4,4'-(N-methylphthalimide) (27507-54-6)

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;

4-nitro-N-methyl-phthalimide (41663-84-7) + recorcinol (108-46-3) → C24H16N2O6

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%

BPA (80-05-7) + 4-nitro-N-methyl-phthalimide (41663-84-7) → 4,4’-bisphenol A-bis-N-methylphthalimide (54395-52-7)

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;

4-nitro-N-methyl-phthalimide (41663-84-7) → 4-amino-N-methylphthalimide (2307-00-8)

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%

4-nitro-N-methyl-phthalimide (41663-84-7) + phenol potassium fluoride → 4-phenoxy-N-methyl phthalimide (63197-24-0)

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

4-nitro-N-methyl-phthalimide (41663-84-7) + phenol (108-95-2) → 4-phenoxy-N-methyl phthalimide (63197-24-0)

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%

4-nitro-N-methyl-phthalimide (41663-84-7) + 4,4'-sulfonediphenol (80-09-1) → C30H20N2O8S

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;

BPA (80-05-7) + 4-nitro-N-methyl-phthalimide (41663-84-7) → N-methyl-N′-methyl-3,3′,4,4′-bisphenol A diether bisphthalimide

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%

5-hydroxy-2-methylisoindoline-1,3-dione (4112-65-6) + 4-nitro-N-methyl-phthalimide (41663-84-7) → oxo-bis-4,4'-(N-methylphthalimide) (27507-54-6)

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

4-nitro-N-methyl-phthalimide (41663-84-7) + 4-hydroxy-benzoic acid (99-96-7) → 4-((N-methylphthalimide)-4-oxy)benzoic acid

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 + 4-nitro-N-methyl-phthalimide (41663-84-7) → oxo-bis-4,4'-(N-methylphthalimide) (27507-54-6)

Conditions	Yield
With potassium acetate	71%

SnCl2 dihydrate + 4-nitro-N-methyl-phthalimide (41663-84-7) → 4-amino-N-methylphthalimide (2307-00-8)

Conditions	Yield
In water	54.7%

4-nitro-N-methyl-phthalimide (41663-84-7) + phenylmagnesium chloride (100-59-4) → 5-anilino-2-methyl-isoindole-1,3-dione (4636-67-3)

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%

p-cresol (106-44-5) + 4-nitro-N-methyl-phthalimide (41663-84-7) → N-Methyl-4-(4-methylphenoxy)phthalimide (72709-41-2)

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

p-cresol (106-44-5) + 4-nitro-N-methyl-phthalimide (41663-84-7) → N-Methyl-4-(4-methylphenoxy)phthalimide (72709-41-2) + 4-(4-Methylphenoxy)phthalic acid (63196-15-6) + N-Methyl-4-nitro-phthalamic acid (72709-47-8) + N-Methyl-5-nitro-phthalamic acid (72709-49-0) + N-Methyl-5-(4-methylphenoxy)phthalamic acid (72709-44-5) + N-Methyl-4-(4-methylphenoxy)phthalamic acid (72709-42-3)

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

4-nitro-N-methyl-phthalimide (41663-84-7) → N-Methyl-4-nitro-phthalamic acid (72709-47-8) + N-Methyl-5-nitro-phthalamic acid (72709-49-0)

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

hydrogenchloride (7647-01-0) + 4-nitro-N-methyl-phthalimide (41663-84-7) + tin dichloride → <4-amino-phthalic acid >-methylimide

4-nitro-N-methyl-phthalimide (41663-84-7) → 4-(2-Amino-1-naphthyldiazenyl)-N-methylnaphthylamid (91289-90-6)

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

Upstream product

• 550-44-7 N-methylphthalimide 
• 89-40-7 4-nitrophthalimide 
• 616-38-6 carbonic acid dimethyl ester 
• 85-44-9 phthalic anhydride 
• 10133-88-7 2-(4-nitrophthalimido)acetic acid 
• 136918-14-4 phthalimide 
• 5466-84-2 4-nitrophthalic anhydride 
• 74-89-5 methylamine 
• 106-44-5 p-cresol 
• 72709-48-9 Sodium; 2-methylcarbamoyl-4-nitro-benzoate 
• 72709-50-3 Sodium; 2-methylcarbamoyl-5-nitro-benzoate 
• 5330-05-2 4-nitrophthalimide potassium salt 
• 74-88-4 methyl iodide 
• 512-56-1 trimethyl phosphite 

Downstream Products

• 2307-00-8 4-amino-N-methylphthalimide 
• 7717-74-0 4-(4-carboxyphenoxy)phthalic acid 
• 18500-03-3 4-(p-carboxyphenoxy)phthalic anhydride 
• 17828-53-4 1,4-bis(3,4-dicarboxyphenoxy)benzene dianhydride 
• 26177-82-2 4,4'-(4,4'-Diphenylendioxy)diphthalsaeureanhydrid 
• 63227-28-1 C₃₀H₂₀N₂O₆ 
• 1823-59-2 4,4'-oxydiphthalic dianhydride 
• 7717-76-2 4,4'-oxydiphthalic acid 
• 38103-06-9 4,4'-bis(4,4'-isopropylidene diphenoxy)-bis(phthalic anhydride) 
• 38103-05-8 2,2-bis[4-(3',4'-dicarboxyphenoxy)phenyl]propane 
• 63197-24-0 4-phenoxy-N-methyl phthalimide 
• 57830-14-5 5-phenoxy-3H-isobenzofuran-1-one 
• 54395-52-7 4,4’-bisphenol A-bis-N-methylphthalimide 
• 4636-67-3 5-anilino-2-methyl-isoindole-1,3-dione 

Relevant articles and documents

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Olive-shaped N-methyl-4-nitrophthalimide crystal and preparation method thereof

The invention relates to an olive-shaped N-methyl-4-nitrophthalimide crystal and a preparation method thereof. The method comprises the steps: a) carrying out a reaction on N-methylphthalimide and fuming nitric acid in a concentrated sulfuric acid system to prepare a concentrated sulfuric acid solution of N-methyl-4-nitrophthalimide; b) pouring the concentrated sulfuric acid solution of N-methyl-4-nitrophthalimide into low-temperature water, stirring, separating out an N-methyl-4-nitrophthalimide solid, washing with water, and drying; and c) refluxing and cooling the dried N-methyl-4-nitrophthalimide solid, and then filtering and drying to obtain the olive-shaped N-methyl-4-nitrophthalimide crystal. According to the invention, the problem that heat accumulation is easy to cause danger in the production process in the prior art is solved while the problems of small product crystal stacking density, difficult feeding in downstream synthesis application and low product yield are also solved.

A process for preparing N - alkyl -4 - nitro phthalimide method (by machine translation)

The invention belongs to the field of organic synthesis technology, and relates to a N - alkyl phthalimide as raw materials, nitric acid as nitrating agent, through the continuous flow at low temperature the nitration reaction preparation N - alkyl - 4 - nitro phthalic acid imide series products. The reaction time is short, the production cycle is short, intermittent reaction kettle solves the problem caused by the accumulation of the raw materials, the reaction process is more stable, significantly improves the reaction efficiency. The different structure of the micro-channel in the reactor to enhance the mass transfer, heat transfer performance, keep the reaction temperature constant, to avoid the phenomenon of the rack frame, to reduce by-product, at the same time improves the safety of the reaction process. The micro-channel of the mass transfer effect of strong in the reactor, so that the liquid - liquid reaction liquid to be fully mixed, in the reaction process, concentrated sulfuric acid, can greatly reduce the consumption of nitric acid, reduces the production of waste. (by machine translation)