93315-97-0

Basic information

• Product Name: 2-mesityl-1H-isoindole-1,3(2H)-dione
• Synonyms: 2-mesityl-1H-isoindole-1,3(2H)-dione;2-(2,4,6-trimethylphenyl)-1H-isoindole-1,3(2H)-dione
• CAS NO: 93315-97-0
• Molecular Formula: C₁₇H₁₅NO₂
• Molecular Weight: 265.3065
• Mol File: 93315-97-0.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-mesityl-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-mesityl-1H-isoindole-1,3(2H)-dione(93315-97-0)
• EPA Substance Registry System: 2-mesityl-1H-isoindole-1,3(2H)-dione(93315-97-0)

Safety Data

• Hazardous Substances Data: 93315-97-0(Hazardous Substances Data)

Upstream product

• 85-44-9 phthalic anhydride 
• 88-05-1 2,4,6-trimethylaniline 
• 422508-64-3 1,3-dioxoisoindolin-2-yl 2,3,4,5,6-pentafluorobenzoate 
• 108-67-8 1,3,5-trimethyl-benzene 
• 136918-14-4 phthalimide 
• 1875-48-5 N-aminophthalamide 
• 59344-64-8 tris(2,4,6-trimethylphenyl)bismuth 
• 5672-90-2 N-(trifluoromethyl)acyloxyphthalimide 
• 524-38-9 N-hydroxyphthalimide 

Downstream Products

• 85-44-9 phthalic anhydride 
• 88-05-1 2,4,6-trimethylaniline 

Relevant articles and documents

Cyclic (aryl)(amido)carbenes: Pushing the π-acidity of amidocarbenes through benzannulation

Cyclic(aryl)(amido)carbenes were synthesized, and studied via a combination of experimental and computational approaches. These carbenes undergo dimerization when isolation is attempted, however, are trapped with sulfur, selenium, and [Ir(cod)Cl]. The π-acidity, measured using 77Se NMR, revealed that these are the most electrophilic singlet carbenes reported to date whereas the TEP measured demonstrated that these carbenes are poor σ donors.

Metal-to-Ligand Ratio-Dependent Chemodivergent Asymmetric Synthesis

Chemodivergent asymmetric synthesis was achieved by tuning the metal-to-ligand ratio in an organometallic catalytic system. Using N-(aroyloxy)phthalimide as the precursor of either an oxygen-centered aroyloxy radical or a nitrogen-centered phthalimidyl radical, enantioselective oxocyanation or aminocyanation of alkenes was achieved separately through a dual photoredox and copper catalysis. The metal-to-ligand ratio can exert chemoselective control while retaining the high enantiopurity of divergent products. Both reactions proceed efficiently with catalyst loading as low as 0.2 mol % and can be performed on a gram scale without loss of chemoselectivity or enantioselectivity. Chemodivergent asymmetric 1,5-aminocyanation or 1,5-oxocyanation of vinylcyclopropane can also be realized by this protocol. Mechanistic investigations involving electron paramagnetic resonance (EPR) experiments were performed to shed light on the stereochemical and chemodivergent results.

Cyclic (Aryl)(Amido)Carbenes: NHCs with Triplet-like Reactivity

The synthesis and study of a library of cyclic (aryl)(amido)carbenes (CArAmCs), which represent a class of electrophilic NHCs that feature low calculated singlet-triplet gaps (ΔEST=19.9 kcal mol?1; B3LYP/def2-TZVP) and exhibit reactivity profiles expected from triplet carbenes, are described. The electrophilic properties of the CArAmCs were quantified by analyzing their respective selenium adducts, which exhibited the largest downfield 77Se NMR chemical shifts (up to 1645 ppm) measured for any NHC derivative known to date, as well as their Ir carbonyl complexes, from which large Tolman electronic parameter (TEP) values (up to 2064 cm?1) were ascertained. The CArAmCs were found to engage in reactions that are typically observed with triplet carbenes, including C?H insertions, [2+1] cycloadditions with alkenes as well as alkynes, and spontaneous oxidation upon exposure to oxygen.