83844-42-2

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2,4-dimethyl-
• Synonyms: N,3-dimethylphthalimide;3-amino-N-methylphthalimide;1,3-dimethylphthalimide;2,3-Dihydro-2,4-dimethyl-1H-isoindole-1,3-dione;N,3-dimethylphtalimide
• CAS NO: 83844-42-2
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.18400
• Mol File: 83844-42-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 136 °C
• Boiling Point: 294.5±19.0 °C(Predicted)
• Density: 1.261±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2,4-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2,4-dimethyl-(83844-42-2)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2,4-dimethyl-(83844-42-2)

Safety Data

• Hazardous Substances Data: 83844-42-2(Hazardous Substances Data)

Upstream product

• 7251-82-3 3-Methylphthalimide 
• 74-88-4 methyl iodide 
• 4792-30-7 3-methylphthalic acid anhydride 
• 593-51-1 methylamine hydrochloride 
• 74-89-5 methylamine 
• 5333-84-6 3-methyl-Δ⁴-tetrahydrophthalic anhydride 

Downstream Products

• 1314499-67-6 ethyl 4-{[(2-methyl-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl)methyl]amino}benzoate 
• 1314499-76-7 4-{[(2-methyl-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl)methyl]amino}benzenesulfonic acid 
• 1314499-79-0 2-methyl-4-({[4-(phenylcarbonyl)phenyl]amino}methyl)-1H-isoindole-1,3(2H)-dione 
• 1314499-83-6 4-{[(2-methyl-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl)methyl]amino}benzonitrile 
• 22948-70-5 2,4-dimethyl-1,3-diphenyisoindole 
• 1149352-11-3 2,4-dimethylisoindoline 
• 122993-63-9 2,3-Dihydro-4-hydroxymethyl-2-methyl-1H-isoindole 

Relevant articles and documents

Identification of the binding modes of N-phenylphthalimides inhibiting bacterial thymidylate synthase through X-ray crystallography screening

To identify specific bacterial thymidylate synthase (TS) inhibitors, we exploited phenolphthalein (PTH), which inhibits both bacterial and human enzymes. The X-ray crystal structure of Lactobacillus casei TS (LcTS) that binds PTH showed multiple binding modes of the inhibitor, which prevented a classical structure-based drug design approach. To overcome this issue, we synthesized two phthalimidic libraries that were tested against TS enzymes and then we performed X-ray crystallographic screening of the active compounds. Compounds 6A, 8A, and 12A showed 40-fold higher affinity for bacterial TS than human TS. The X-ray crystallographic screening characterized the binding mode of six inhibitors in complexes with LcTS. Of these, 20A, 23A, and 24A showed a common unique binding mode, whereas 8A showed a different, unique binding mode. A comparative analysis of the LcTS X-ray complexes that were obtained with the pathogenic TS enabled the selection of compounds 8A and 23A as specific compounds and starting points to be exploited for the specific inhibition of pathogen enzymes.

Synthesis and Mass Spectrometric Fragmentation of Dihydroisoindole Derivatives

C-8-substituted N-methyl-1,2,3,4-tetrahydroisoquinoline radical cations lose the complete substituent in a one step reaction giving rise to an unexpected ion at m/z 146, which is probably identical with the dihydroisoindolylmethyl-cation A.The dihydroisoindoles 1, 10, and 16 were prepared as potentially alternative precursors of ion A.Hovever, the ion at m/z 146 in their EI mass spectra is of very low intensity, so CID-experiments for structural comparison could not be performed.The electron impact induced fragmentations of 1, 10, and 16 are discussed.