N-Methylphthalimide supplier

Name
N-Methylphthalimide
EINECS 208-982-4
CAS No. 550-44-7
Article Data169
CAS DataBase
Density 1.314 g/cm³
Solubility
Melting Point 129-132 °C(lit.)
Formula C₉H₇NO₂
Boiling Point 286 °C at 760 mmHg
Molecular Weight 161.16
Flash Point 117.4 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 37.38000
LogP 0.85030

Synthetic route

: 67-56-1
methanol

: 136918-14-4
phthalimide

: 550-44-7
N-methylphthalimide

Conditions

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

Conditions	Yield
With hydrogenchloride at 20℃; under 750.06 Torr; Cyclization; solid-gas reaction;	100%
With water
at 190℃;
at 190℃;

: 136918-14-4
phthalimide

: 431-47-0
trifluoroacetic acid-methyl ester

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With sodium methylate; sodium hydride In dimethyl sulfoxide at 20℃; for 10h;	100%

: 136918-14-4
phthalimide

: 50-00-0
formaldehyd

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen In water at 75 - 80℃; pH=5.5; Temperature; Concentration; Autoclave; Inert atmosphere;	99.33%
at 150 - 160℃;

: 85-44-9
phthalic anhydride

: 74-89-5
methylamine

: 550-44-7
N-methylphthalimide

Conditions

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%

: 4702-13-0
N-phthaloylglycine

: 550-44-7
N-methylphthalimide

Conditions

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%

: 136918-14-4
phthalimide

: 616-38-6
carbonic acid dimethyl ester

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In N,N-dimethyl-formamide at 95℃; for 8h;	95%

: 88-67-5
2-Iodobenzoic acid

: 201230-82-2
carbon monoxide

: 74-89-5
methylamine

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With triethylamine In toluene at 100℃; under 760.051 Torr; for 4h; Autoclave;	95%

...Expand

: 64-18-6
formic acid

: 58084-22-3
2-iodo-N-methyl-benzamide

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With iodine; palladium diacetate; triethylamine; triphenylphosphine In toluene at 80℃; for 2h;	95%

: 88070-48-8
N-methylbenzamide

: 201230-82-2
carbon monoxide

: 550-44-7
N-methylphthalimide

Conditions

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%

: 2021-21-8
N-methyl-1,2,5,6-tetrahydrophthalimide

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With palladium (II) trifluoroacetate; sodium anthraquinone-2-sulfonate; oxygen; magnesium sulfate In chlorobenzene at 110℃; under 760.051 Torr; for 24h; Sealed tube;	94%

: 109124-50-7
methyl N-methyl-N-carbethoxyphthalamate

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With sodium In toluene for 2h; Heating;	93%

: 6843-36-3
2-(methylcarbamoyl)benzoic acid.

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
In water; toluene for 3h; Heating;	93%

: 135354-98-2
3-(p-tolylimino)-isoindolinone

: 74-88-4
methyl iodide

A: 550-44-7
N-methylphthalimide

B: 84628-32-0
(E)-2-methyl-3-(p-tolylimino)-isoindolinone

C: 84628-34-2
3-N-methyl-N(p-tolyl)amino-isoindoleninone

Conditions

Conditions	Yield
In toluene at 120℃; for 24h; in a pressure tubing;	A 2% B 6% C 92%

...Expand

: 136918-14-4
phthalimide

: 74-88-4
methyl iodide

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With potassium hydroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃; for 5h;	91%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 18h;	90%
With potassium fluoride; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 25℃; for 5h;	88%

: 136918-14-4
phthalimide

: 6257-10-9
N,N'-dicyclohexyl-O-methyl isourea

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 2h;	90%

: 1914-20-1
N-methoxyphthalimide

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With triisopropyl phosphite; acetic acid at 100℃; for 15h;	90%

: 74-89-5
methylamine

: 17858-14-9
dimethyl (1-chloro-1,3-dihydro-3-oxo-1-isobenzofuranyl)phosphonate

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With triethylamine In acetonitrile for 0.166667h;	89%

: 33081-78-6
sodium phthalimide

: [(E)-2-(4-chlorophenyl)ethenyl]dimethylsulfonium triflate

A: 550-44-7
N-methylphthalimide

B: 25650-51-5
(E)-4-chlorostyryl methyl sulfide

Conditions

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 20℃;	A 58% B 88%

...Expand

: 2913-97-5
N-phthalimidyl-2-aminoacetaldehyde

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
rhodium(III) chloride; 1,3-bis-(diphenylphosphino)propane In diethylene glycol dimethyl ether for 16h; Heating;	87%

: 746677-26-9
(E)-2-(4-(dimethylamino)-2-oxobut-3-enyl)isoindoline-1,3-dione

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With zeolite at 160℃; for 0.5h; Microwave irradiation; Neat (no solvent);	87%

: 58084-22-3
2-iodo-N-methyl-benzamide

: 1864-94-4
phenyl formate

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; N,N,N,N,-tetramethylethylenediamine; triethylamine at 80℃; for 18h; Inert atmosphere; Schlenk technique;	87%

: 3481-09-2
N-chlorophthalimide

: 74-88-4
methyl iodide

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; for 0.1h;	87%

: 155793-97-8
endo,endo-2,3-dibromo-7-oxanorborneno<2,3-c>succinimide

A: 550-44-7
N-methylphthalimide

B: 99529-42-7
N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide

Conditions

Conditions	Yield
With hydrogen; silver; zinc In tetrahydrofuran for 0.0833333h; Heating;	A 15% B 85%

: 14204-26-3
N-(benzylthio)phthalimide

: 121-45-9
phosphorous acid trimethyl ester

A: 550-44-7
N-methylphthalimide

B: 7205-16-5
O,O-dimethyl S-(benzyl) phosphorothioate

Conditions

Conditions	Yield
In toluene Ambient temperature;	A n/a B 85%

...Expand

: 117194-00-0
N-methyl-2-formylbenzamide

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
Stage #1: N-methyl-2-formylbenzamide With copper(I) bromide In tetrachloromethane; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In tetrachloromethane; acetonitrile at 75℃; for 12h; Inert atmosphere;	85%

: 18042-62-1
N-<(Trimethylsilyl)methyl>phthalimide

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
In acetonitrile Irradiation;	83%
In acetonitrile for 24h; Irradiation;	81%

: 122504-70-5
N-Octadecylthiophthalimid

: 121-45-9
phosphorous acid trimethyl ester

A: 550-44-7
N-methylphthalimide

B: 128371-61-9
Thiophosphoric acid O,O'-dimethyl ester S-octadecyl ester

Conditions

Conditions	Yield
In toluene Ambient temperature;	A n/a B 83%

...Expand

: 1074-82-4
potassium phtalimide

: 74-88-4
methyl iodide

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Ambient temperature;	82%
In N,N-dimethyl-formamide for 1h; Reflux;	80%
at 150℃;
In N,N-dimethyl-formamide for 3h; Ambient temperature;
In N,N-dimethyl-formamide for 1h; Reflux;

: 16050-53-6
C28H18CuN4O4

: 550-44-7
N-methylphthalimide

Conditions

Conditions	Yield
With di-tert-butyl peroxide; bis(1-methyl-1-phenylethyl)peroxide In acetonitrile at 100℃; for 18h; Inert atmosphere; Glovebox;	81%

: 550-44-7
N-methylphthalimide

: 100-58-3
phenylmagnesium bromide

: 26597-63-7
3-hydroxy-2-methyl-3-phenyl-2,3-dihydro-isoindol-1-one

Conditions

Conditions	Yield
Stage #1: N-methylphthalimide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 3h; Grignard reaction; Inert atmosphere; Stage #2: With water In tetrahydrofuran; diethyl ether Grignard reaction;	100%

: 550-44-7
N-methylphthalimide

: 39976-03-9
2-(hydroxymethyl)-N-methylbenzamide

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; potassium tert-butylate; hydrogen In tetrahydrofuran; isopropyl alcohol at 40℃; under 30003 Torr; for 15h; Autoclave; Sealed tube;	99%
With sodium tetrahydroborate In water; isopropyl alcohol; toluene at 0℃; for 4h; Yield given;
With sodium tetrahydroborate In water; isopropyl alcohol; toluene

: 550-44-7
N-methylphthalimide

: 90224-73-0
5-bromo-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione

Conditions

Conditions	Yield
With sulfuric acid; 5,5-dibromohydantoin at 20℃; for 6h; Sealed tube;	98.4%

: 550-44-7
N-methylphthalimide

: 29879-69-4
3-hydroxy-2-methyl-isoindolin-1-one

Conditions

Conditions	Yield
With hydrogen; sodium hydroxide In toluene at 40℃; under 30003 Torr; for 24h;	97%
With ethanol; tetrabutylammonium tetrafluoroborate; diisopropylamine at 20℃; for 2h; Electrochemical reaction; Schlenk technique; Green chemistry; chemoselective reaction;	91%
With acetic acid; zinc at 60℃; for 0.166667h;	75%

: 550-44-7
N-methylphthalimide

: 107-13-1
acrylonitrile

: 1001428-10-9
3-(1-hydroxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionitrile

Conditions

Conditions	Yield
With samarium diiodide; tert-butyl alcohol In tetrahydrofuran at -30℃; for 1.5h;	97%
With ammonia; water; zinc In dichloromethane at 20℃; under 760.051 Torr; for 4h; Cooling with ice;	81%

: 550-44-7
N-methylphthalimide

: 3474-87-1
2-methylisoindoline

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 2h; Heating;	96%
With borane In tetrahydrofuran for 6h; Reflux;	80%
With sulfuric acid at 85℃; Electrolysis.Verwendung einer amalgamierten Zink-Kathode;

: 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%

: 550-44-7
N-methylphthalimide

: 75-16-1
methylmagnesium bromide

: 29879-71-8
1-hydroxy-1,2-dimethyl-2,3-dihydro-3-oxo-1H-isoindole

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at -30 - -5℃; for 2h;	96%

: 550-44-7
N-methylphthalimide

: 1238840-05-5
C10H10NO3(1-)*K(1+)

: 1238840-23-7
N-[(1-hydroxy-2-methyl-3-oxoisoindolin-1-yl)methyl]-N-phenylacetamide

Conditions

Conditions	Yield
In water; acetone at 15 - 20℃; for 1h; UV-irradiation; Inert atmosphere;	95%

: 67-56-1
methanol

: 550-44-7
N-methylphthalimide

: 2,3-dihydro-3-methoxy-2-methyl-1H-isoindol-1-one

Conditions

Conditions	Yield
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 90℃; under 15001.5 Torr; for 18h; Kinetics; Catalytic behavior; Temperature; Pressure; Reagent/catalyst; Sealed tube; Autoclave; Green chemistry;	95%
With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 130℃; under 11251.1 Torr; for 18h; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave;

: 550-44-7
N-methylphthalimide

: 71-41-0
pentan-1-ol

: C14H19NO2

Conditions

Conditions	Yield
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In neat (no solvent) at 90℃; under 15001.5 Torr; for 18h; Sealed tube; Autoclave; Green chemistry;	95%

: 550-44-7
N-methylphthalimide

: 1119-51-3
bromopentene

: C14H17NO

Conditions

Conditions	Yield
Stage #1: bromopentene With magnesium In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: N-methylphthalimide In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; Stage #3: With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at -20 - 0℃; for 0.5h; Inert atmosphere;	95%

: 550-44-7
N-methylphthalimide

: 67-63-0
isopropyl alcohol

: C12H15NO2

Conditions

Conditions	Yield
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In neat (no solvent) at 90℃; under 15001.5 Torr; for 18h; Sealed tube; Autoclave; Green chemistry;	94%
With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 130℃; under 11251.1 Torr; for 18h; Autoclave;	87%

: 530-48-3
1,1-Diphenylethylene

: 550-44-7
N-methylphthalimide

A: 41977-31-5
1,1,4-triphenyl-1,2,3,4-tetrahydronaphthalene

B: 92172-54-8
3-(diphenylmethylene)-2-methyl-2,3-dihydro-1H-isoindole-1-one

C: 95363-11-4
6,7-dihydro-6,6-diphenyl-1-methyl-3,4-benzazepine-2,5-dione

Conditions

Conditions	Yield
In acetonitrile for 3h; Mechanism; also in the presence of phenanthrene;	A 93% B 10% C 11%
In acetonitrile for 3h; Irradiation;	A 93% B 10% C 11%

...Expand

: 550-44-7
N-methylphthalimide

: 4192-77-2
ethyl cinnamate

: 3-(1-hydroxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)3-phenylpropionic acid ethyl ester

Conditions

Conditions	Yield
With samarium diiodide; tert-butyl alcohol In tetrahydrofuran at 0℃; for 3h;	93%

: 550-44-7
N-methylphthalimide

: 67433-97-0
potassium (2-methylphenoxy)acetate

: 1197155-41-1
C17H17NO3

Conditions

Conditions	Yield
In water; acetone at 15 - 20℃; for 1h; Irradiation; Inert atmosphere;	93%

: 550-44-7
N-methylphthalimide

: 109-86-4
2-methoxy-ethanol

: 3-(2-methoxyethoxy)-2-methylisoindolin-1-one

Conditions

Conditions	Yield
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In neat (no solvent) at 90℃; under 15001.5 Torr; for 18h; Sealed tube; Autoclave; Green chemistry;	93%
With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 130℃; under 11251.1 Torr; for 18h; Autoclave;	90%

N-Methylphthalimide Consensus Reports

Reported in EPA TSCA Inventory.

N-Methylphthalimide 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%.

Uses of N-Methylphthalimide: it can be used to produce N-bromomethyl-phthalimide at temperature of 160 - 170 °C. It will need reagent bromine.

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.

Product Name

N-Methylphthalimide

Synthetic route

N-Methylphthalimide Consensus Reports

N-Methylphthalimide Specification

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