ChemicalBook Product Catalog Chemical Reagents Organic reagents Imide N-Methylphthalimide

N-Methylphthalimide

N-Methylphthalimide Basic information
Product Name:N-Methylphthalimide
Synonyms:2-Methyl-1H-isoindole-1;Rivaroxaban Impurity F ( N-Methyl Phthalimide ) CAS No. 550-44-7;Imp. F:N-Methylphthalimide;Rivaroxaban impurity P1-B;1H-Isoindole-1,3(2H)-dione,2-methyl-;2-Methyl-1H-isoindol-1,3(2H)-dion;2-methyl-1h-isoindole-3(2h)-dione;2-Methyl-isoindole-1,3-dione
CAS:550-44-7
MF:C9H7NO2
MW:161.16
EINECS:208-982-4
Product Categories:intermediates;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Cyclic ImidesDerivatization Reagents;Carbonyl Compounds;Derivatization Reagents HPLC;Organic Building Blocks;UV-VIS;API intermediates
Mol File:550-44-7.mol
N-Methylphthalimide Structure
N-Methylphthalimide Chemical Properties
Melting point 129-132 °C (lit.)
Boiling point 286.05°C
density 1.2443 (rough estimate)
refractive index 1.4500 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka-2.09±0.20(Predicted)
color White to Off-White
BRN 124428
CAS DataBase Reference550-44-7(CAS DataBase Reference)
NIST Chemistry Reference1H-Isoindole-1,3(2H)-dione, 2-methyl-(550-44-7)
EPA Substance Registry System1H-Isoindole-1,3(2H)-dione, 2-methyl- (550-44-7)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 1
RTECS TI5602700
TSCA Yes
HazardClass IRRITANT
HS Code 29251900
MSDS Information
ProviderLanguage
N-Methylphthalimide English
SigmaAldrich English
ALFA English
N-Methylphthalimide Usage And Synthesis
Chemical PropertiesWhite powder
UsesPhotoreduction of N-methylphthalimide (NMP) with 2,3-dimethyl-2-butene h and the selective electroreduction of N-methylphthalimide to 3-hydroxy-2-methyl-isoindolin-1-one have been studied.
Synthesis Reference(s)The Journal of Organic Chemistry, 44, p. 497, 1979 DOI: 10.1021/jo01318a005
General DescriptionPhotoreduction of N-methylphthalimide (NMP) with 2,3-dimethyl-2-butene has been studied. The selective electroreduction of N-methylphthalimide to 3-hydroxy-2-methyl-isoindolin-1-one in ionic liquids and phenol as a proton donor under silent and ultrasonic conditions has been reported. Single electron transfer (SET)-induced photochemical reaction of NMP with silyl enol ether has been investigated. Nitration of NMP is reported to afford “exclusively” 3-nitro-derivative.
Purification MethodsRecrystallise the imide from absolute EtOH or AcOH (m 134o). The IR has max at 1780 and 1380cm -1. [Beilstein 21 H 461, 21 III/IV 5030.]
N-Methylphthalimide Preparation Products And Raw materials
Preparation ProductsN-Methyl-3-nitrophthalimide-->4-Nitro-N-methylphthalimide-->N-(Bromomethyl)phthalimide-->4-AMINO-N-METHYLPHTHALIMIDE
4-METHYLPHTHALIMIDE 4-PROPIONYLAMINO-N-METHYLPHTHALIMIDE 4-DIMETHYLAMINO-N-METHYLPHTHALIMIDE Bismaleimide 4-ETHYLAMINO-N-METHYLPHTHALIMIDE 1,2,3,6-tetrahydro-N-methylphthalimide N-(4-AMINO-2-METHYLPHENYL)-4-CHLOROPHTHALIMIDE 4-AMINO-N-METHYLPHTHALIMIDE,3-AMINO-N-METHYLPHTHALIMIDE 4-(P-ACETYLAMINO)BENZOYLAMINO-N-METHYLPHTHALIMIDE 3,4,5,6-tetrachloro-N-methylphthalimide N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE 4-AMINO-N-METHYLPHTHALIMIDE N-Isopropylphthalimide 4-METHYLPHTHALIMIDE 96% C9H7NO2 FW161.16,4-METHYLPHTHALIMIDE 99 4-PYRROLIDINYL-N-METHYLPHTHALIMIDE 4-DIETHYLAMINO-N-METHYLPHTHALIMIDE DIETHYL 2-PHTHALIMIDOMALONATE-2-13C N-Phenyl-4-methylphthalimide
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