304-19-8

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-(2-methylethyl)- (9CI)
• Synonyms: 1H-Isoindole-1,3(2H)-dione, 2-(2-methylethyl)- (9CI);2-(2-methylpropyl)isoindole-1,3-dione
• CAS NO: 304-19-8
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.24
• Mol File: 304-19-8.mol

Chemical Properties

• Boiling Point: 294°Cat760mmHg
• Flash Point: 126.2°C
• Appearance: /
• Density: 1.171g/cm³
• Vapor Pressure: 0.00167mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-(2-methylethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-(2-methylethyl)- (9CI)(304-19-8)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-(2-methylethyl)- (9CI)(304-19-8)

Safety Data

• Hazardous Substances Data: 304-19-8(Hazardous Substances Data)

Usage

Classification

Organic compound

Use in production

Pharmaceutical drugs

Role

Intermediate in organic synthesis

Potential applications

Medicinal chemistry, development of new medications

Other uses

Industrial applications, reagent in various chemical reactions

InChI:InChI=1/C12H13NO2/c1-8(2)7-13-11(14)9-5-3-4-6-10(9)12(13)15/h3-6,8H,7H2,1-2H3

Upstream product

• 85-44-9 phthalic anhydride 
• 78-81-9 isobutylamine 
• 1189-23-7 N,N'-di-isobutylurea 
• 88-95-9 Phthaloyl dichloride 
• 6306-54-3 N-phthaloyl L-valine 
• 203852-64-6 rac-1-(1,3-dioxoisoindolin-2-yl)-2-methylpropyl acetate 
• 13380-30-8 2-isobutylisoindoline-1-one 
• 612-13-5 2-cyanobenzyl chloride 
• 5115-65-1 N-phthaloyl-DL-valine 
• 136918-14-4 phthalimide 
• 78-77-3 Isobutyl bromide 
• 3481-09-2 N-chlorophthalimide 
• 2125731-81-7 1,3-dioxoisoindolin-2-yl 3-methylbutanoate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 381675-24-7 C₁₉H₂₁NO₂ 
• 352-32-9 p-fluorotoluene 
• 1407166-66-8 C₁₉H₂₀FNO₂ 
• 6140-17-6 4-methylbenzotrifluoride 
• 1407166-67-9 C₂₀H₂₀F₃NO₂ 

Relevant articles and documents

“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides

An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.

Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene

While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C-C bond formations, the corresponding C(sp3)-N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp3)-(N)phth, secondary C(sp3)-I, or tertiary C(sp3)-(meta C)phth coupling products. The primary C(sp3)-(N)phth coupling offers convenient access to primary amines.

Method for constructing N-isobutylphthalimide in one step by using imine as starting material

The invention discloses a method for constructing N-isobutylphthalimide in one step by using imine as a starting material. According to the method, (E)-N-isobutyl-1-phenylmethylenimine is used as a reaction raw material and subjected to a carbonylation reaction to construct N-isobutylphthalimide in one step. The method has the characteristics of mild reaction conditions, simple operation procedures and excellent yield.

Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile

Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.

Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement

The Curtius rearrangement is a classic, powerful method for converting carboxylic acids into protected amines, but its widespread use is impeded by safety issues (the need to handle azides). We have developed an alternative to the Curtius rearrangement that employs a copper catalyst in combination with blue-LED irradiation to achieve the decarboxylative coupling of aliphatic carboxylic acid derivatives (specifically, readily available N-hydroxyphthalimide esters) to afford protected amines under mild conditions. This C-N bond-forming process is compatible with a wide array of functional groups, including an alcohol, aldehyde, epoxide, indole, nitroalkane, and sulfide. Control reactions and mechanistic studies are consistent with the hypothesis that copper species are engaged in both the photochemistry and the key bond-forming step, which occurs through out-of-cage coupling of an alkyl radical.

Metal-free C-N cross-coupling of electrophilic compounds and N-haloimides

When DBU is added, the cross-coupling reaction between alkyl halides (halogen = Cl, Br and I) and N-haloimides (halogen = Cl, Br) occurs, resulting in the formation of aminated products. A halogen bond activated nucleophilic substitution mechanism was proposed. The methodology represents an elegant example of applying the halogen bond activation strategy in an organic transformation.

A metal-free approach for transamidation of amides with amines in aqueous media

An efficient, environmentally benign and a mild protocol for transamidation of amides with a variety of amines in the presence of K2S2O8 using stoichiometric quantity in aqueous conditions has been established. This method works under conventional thermal conditions and in microwave irradiation as well. A series of amides have been prepared using this reaction and this is a greener protocol for transamidation, which offers a diverse kind of substrate scope with exclusive product formation (yields 90-98%).

The potential of methylsiloxanes as solvents for synthetic chemistry applications

The potential use of volatile methylsiloxanes (VMSs) as solvents for chemicals synthesis has been explored. Assessment of the environmental impact of these VMS solvents is made and found to be significantly lower than those of the non-polar organic solvents that they have the potential to replace. The polarities of the VMSs, as expressed by empirical polarity measurements, and miscibilities with other liquids are found to be similar to those of alkane solvents. Finally, some uses of VMSs as solvents for both organic and inorganic transformations are described. The VMSs provide environmentally more sustainable (greener) alternatives to the nonpolar solvents that they have the potential to replace.

Isoindolone derivatives, preparation process and intermediates of this process, their use as medicaments, and pharmaceutical compositions comprising them

The present invention relates to the novel isoindolone derivatives of the formula I in which R1 to R6 have the meanings stated in the claims. The inventive compounds are suitable as antiarrhythmic medicaments with a cardioprotective component for infarction prophylaxis and infarction treatment and for the treatment of angina pectoris. They also inhibit in a preventive manner the pathophysiological processes associated with the development of ischemia-induced damage, in particular in the triggering of ischemia-induced cardiac arrhythmias and of heart failure.

N- ((3-OXO2, 3-DIHYDRO-1H-ISOINDOL-1-YL) ACETYL) GUANIDINE DERIVATIVES AS NHE-1 INHIBITORS FOR THE TREATMENT OF INFARCTION AND ANGINA PECTORIS

Isoindolone derivatives, preparation process and intermediates of this process, their use as medicaments, and pharmaceutical compositions comprising them. The present invention relates to the novel isoindolone derivatives of the Formula (I), in which R1 to R6 have the meanings stated in the claims. The inventive compounds are suitable as antiarrhythmic medicaments with a cardioprotective component for infarction prophylaxis and infarction treatment and for the treatment of angina pectoris. They also inhibit in a preventive manner the pathophysiological processes associated with the development of ischemia-induced damage, in particular in the triggering of ischemia-induced cardiac arrhythmias and of heart failure.