5399-20-2

Basic information

• Product Name: 2-(2-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione
• CAS NO: 5399-20-2
• Molecular Formula: C₁₄H₁₅NO₃
• Molecular Weight: 245.2738
• Mol File: 5399-20-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 410.1°C at 760 mmHg
• Flash Point: 201.8°C
• Density: 1.365g/cm³
• Vapor Pressure: 1.85E-07mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 2-(2-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione(5399-20-2)
• EPA Substance Registry System: 2-(2-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione(5399-20-2)

Safety Data

• Hazardous Substances Data: 5399-20-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione is used as a valuable intermediate for the synthesis of biologically active compounds. Its unique structure and properties make it a promising candidate for the development of new drugs.
Used in Agrochemicals:
2-(2-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione has potential applications in the field of agrochemicals, where it can be utilized as a starting material for the production of various agrochemical products.
Used in Materials Science:
In the field of materials science, 2-(2-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione has potential uses due to its unique structure and properties, which could contribute to the development of new materials with specific characteristics.
Further research and development of this compound could lead to the discovery of new therapeutic agents and other valuable products in various industries.

Upstream product

• 85-44-9 phthalic anhydride 
• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 24037-87-4 2-(2-oxo-cyclohexyl)-isoindole-1,3-dione 
• 286-20-4 cyclohexane-1,2-epoxide 

Downstream Products

• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 1491151-39-3 (1R,2S)-cis-2-phthalimido-1-acetoxycyclohexane 
• 1491151-37-1 (1S,2R)-cis-2-phthalimidocyclohexanol 
• 1491151-36-0 (1S,2S)-trans-2-phthalimidocyclohexanol 
• 1491151-40-6 (1R,2R)-trans-2-phthalimido-1-acetoxycyclohexane 
• 931-15-7 (1R,2R)-2-aminocyclohexanol 
• 216586-54-8 2-((1R,2R)-2-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione 
• 1360145-99-8 (1S,2S)-(+)-2-phthalimido-1-acetoxy-cyclohexane 

Relevant articles and documents

Interrupting the Barton?McCombie reaction: Aqueous deoxygenative trifluoromethylation of o-alkyl thiocarbonates

The site-selective trifluoromethylation of aliphatic systems remains an important challenge. This work describes a light-driven, copper-mediated trifluoromethylation of O-alkyl thiocarbonates. The reaction provides broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), thereby offering orthogonality and practicality for trifluoromethylation. A radical organometallic mechanism is proposed.

Enzymatic transesterification of pharmacologically interesting β-aminocycloalkanol precursors

Chemoenzymatic syntheses of both enantiomers of cis- and trans-2-aminocyclopentanol as well as cis- and trans-2-aminocyclohexanol, which are valuable building blocks for a plethora of ligands and pharmaceuticals have been efficiently carried out. The strategy involves the stereospecific syntheses of racemic aminocycloalkanol precursors via tagging of a phthalimide as a masking group and subsequent lipase-catalyzed kinetic resolution. Most of the lipases exhibited excellent enantioselectivity (E a‰ 200) in the transesterification reactions of trans-derivatives, with both N-protected (R,R)-amino acetates and (S,S)-amino alcohols being isolated in enantiopure form. With regard to cis-derivatives, lipases were also very selective, even though the biotransformations were significantly slower.

Efficient preparation of biologically important 1,2-amino alcohols

An efficient three-step methodology developed for the preparation of 1,2-amino alcohols. In the first step a rapid coupling between bromoketones and potassium phthalimide in ionic liquid produced-phthalimido ketones in quantitative yields, which is followed by a facile reduction using NaCNBH 3 in acetic acid to give corresponding phthalimido alcohols and finally effecting hydrazinolysis in water at 60C to yield biologically important 1,2-amino alcohols.

Cyclic trans-β-amino alcohols: Preparation and enzymatic kinetic resolution

Enantioenriched cyclic β-amino alcohols, trans-2-aminocyclohexanols (ee, >99%), trans-2-aminocyclopentanols (ee, >99%), trans-1-amino-2- indanols (ee, >99%) and trans-2-amino-1-indanols (ee, ～98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution.