26491-47-4

Basic information

• Product Name: 2-phenylhexahydro-1H-isoindole-1,3(2H)-dione
• Synonyms: 1H-isoindole-1,3(2H)-dione, hexahydro-2-phenyl-; 2-Phenylhexahydro-1H-isoindole-1,3(2H)-dione; 2-Phenyl-hexahydro-isoindole-1,3-dione
• CAS NO: 26491-47-4
• Molecular Formula: C₁₄H₁₅NO₂
• Molecular Weight: 229.2744
• Mol File: 26491-47-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 445.9°C at 760 mmHg
• Flash Point: 216.2°C
• Density: 1.213g/cm³
• Vapor Pressure: 3.81E-08mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: 2-phenylhexahydro-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenylhexahydro-1H-isoindole-1,3(2H)-dione(26491-47-4)
• EPA Substance Registry System: 2-phenylhexahydro-1H-isoindole-1,3(2H)-dione(26491-47-4)

Safety Data

• Hazardous Substances Data: 26491-47-4(Hazardous Substances Data)

Upstream product

• 20141-47-3 cis-2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione 
• 62-53-3 aniline 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 85-42-7 1,2-Cyclohexanedicarboxylic acid-anhydride 

Downstream Products

• 92670-99-0 cis-2-phenyl-octahydroisoindole-1,3-dione 
• 83248-62-8 12-Phenyl-12-aza-tricyclo[4.4.3.0^1,6]tridecane-11,13-dione 
• 83248-63-9 (1R,7S)-13-Phenyl-13-aza-tricyclo[5.4.3.0^1,7]tetradecane-12,14-dione 
• 83248-64-0 3a-Allyl-2-phenyl-hexahydro-isoindole-1,3-dione 
• 83248-61-7 (1S,6R)-8-Phenyl-8-aza-tricyclo[4.3.3.0^1,6]dodecane-7,9-dione 
• 83248-59-3 (3aS,7aR)-3a,7a-Dimethyl-2-phenyl-hexahydro-isoindole-1,3-dione 
• 83248-56-0 C₁₄H₁₃NO₂^(2-)*2Li⁽¹⁺⁾ 

Relevant articles and documents

Site-Selective Ruthenium-Catalyzed C-H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group

Biologically relevant N-arylisoindolinones efficiently underwent arylation reactions under ruthenium catalysis via C-H bond functionalization. The reactions exclusively led to monoarylated products, and only ortho selectivity was observed in the aromatic ring connected to the nitrogen atom. Interestingly, no C-H bond functionalization was observed in the other benzene ring in the ortho position with respect to the carbonyl group. This ruthenium-catalyzed reaction displayed a high functional group tolerance, and it employed readily available and benchmark stable boronic acid and potassium aryltrifluoroborate derivatives as coupling partners. An appealing late-stage functionalization of indoprofen applying this methodology is showcased.

Ruthenium(ii)-catalysed selective C(sp2)-H bond benzoxylation of biologically appealing: N -arylisoindolinones

Site- and regio-selective aromatic C-H bond benzoxylations were found to take place using biologically appealing N-arylisoindolinones under ruthenium(ii) catalysis in the presence of (hetero)aromatic carboxylic acid derivatives as coupling partners. Besides the presence of two potential C(sp2)-H sites available for functionalization in the substrates, exclusive ortho selectivity was achieved in the phenyl ring attached to the nitrogen atom. Notably, the reactions occurred in a selective manner as only mono-functionalized products were formed and they tolerated a large number of functional chemical groups. The ability of the cyclic tertiary amide within the isoindolinone skeleton to act as a weak directing group in order to accommodate six-membered ring ruthenacycle intermediates appears to be the key to reach such high levels of selectivity. In contrast, the more sterically demanding cyclic imides were unreactive under identical reaction conditions.

Comparative Study of the Reactions of Dilithiated Vicinal Diesters and Dilithiated 1,2-Dicarboximides with Methyl Iodide, α,ω-Dihalides, α,ω-Ditosylates, and ω-Bromo Esters

The reactions od dilithiated dimethyl cyclohexane-1,2-dicarboxylate (1), dimethyl 4-cyclohexene-1,2-dicarboxylate (2), N-substituted cyclohexane-1,2-dicarboximides 11a-c, and N-phenyl-4-cyclohexene-1,2-dicarboximides 18 with a variety of substrates have b