304-17-6

Basic information

• Product Name: N-Isopropylphthalimide
• Synonyms: 1H-Isoindole-1,3(2H)-dione,2-(1-methylethyl)-;2-(1-methylethyl)-1h-isoindole-3(2h)-dione;2-Isopropyl-isoindole-1,3-dione;n-isopropilftalimmide;n-isopropylftalimid;n-isopropyl-phthalimid;N-ISOPROPYL PHTHALIMIDE;ISOPROPYLPHTHALIMIDE
• CAS NO: 304-17-6
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• EINECS: 206-150-5
• Product Categories: Derivatives of phthalimide
• Mol File: 304-17-6.mol

Chemical Properties

• Melting Point: 82-84°C
• Boiling Point: 273°C(lit.)
• Flash Point: 121.1 °C
• Appearance: slight yellow liquid
• Density: 1.1596 (rough estimate)
• Vapor Pressure: 0.00253mmHg at 25°C
• Refractive Index: 1.5012 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.15±0.20(Predicted)
• CAS DataBase Reference: N-Isopropylphthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Isopropylphthalimide(304-17-6)
• EPA Substance Registry System: N-Isopropylphthalimide(304-17-6)

Safety Data

• RTECS: TI5425000
• Hazardous Substances Data: 304-17-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H11NO2/c1-7(2)12-10(13)8-5-3-4-6-9(8)11(12)14/h3-7H,1-2H3

Upstream product

• 85-44-9 phthalic anhydride 
• 75-31-0 isopropylamine 
• 1074-82-4 potassium phtalimide 
• 75-26-3 isopropyl bromide 
• 78-77-3 Isobutyl bromide 
• 20320-33-6 2-(isopropylcarbamoyl)benzoic acid 
• 524-38-9 N-hydroxyphthalimide 
• 1914-20-1 N-methoxyphthalimide 
• 17858-14-9 dimethyl (1-chloro-1,3-dihydro-3-oxo-1-isobenzofuranyl)phosphonate 
• 136918-14-4 phthalimide 
• 67-63-0 isopropyl alcohol 
• 75-30-9 2-iodo-propane 
• 88-95-9 Phthaloyl dichloride 
• 5440-69-7 N-isopropylbenzamide 

Downstream Products

• 75-31-0 isopropylamine 
• 32003-14-8 4-benzyl-2H-phthalazin-1-one 
• 1265964-66-6 2-isopropyl-1-phenyisoindole 
• 1265964-63-3 2-isopropyl-1,3-diphenyisoindole 
• 55023-86-4 2-Isopropyl-2H-isoindol 
• 65399-00-0 2,3-dihydro-2-(1-methylethyl)-1H-isoindol-1-one 
• 5440-69-7 N-isopropylbenzamide 

Relevant articles and documents

Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides

Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heteroc

Preparation method of N-alkyl phthalimide

The invention discloses a preparation method of N-alkyl phthalimide. The method comprises the steps: taking phthalic anhydride as a raw material, taking an aqueous solution of alkylamine as an imidization reagent ( no other reagents do not need to be added), and directly synthesizing the N-alkyl phthalimide, wherein the yield is high (96% or above), and the purity is high (99% or above). The preparation method is loose in reaction condition, simple in step and easy to implement; no organic solvent is needed, no other substances are discharged except water, and the method is green, free of pollution and suitable for industrial production.

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

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

PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides

A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.

Method for synthesizing N-isopropylphthalimide

The invention discloses a method for synthesizing N-isopropylphthalimide. Phthalimide and propylene used as main reaction substrates undergo a nucleophilic addition reaction under the catalysis of a catalyst at a reaction temperature of 50-200 DEG C for 1-30 h to obtain the N-isopropylphthalimide, wherein a molar ratio of phthalimide to propylene in the reaction system is 1:1 to 1:10. The phthalimide and propylene used in the method are all cheap and easily-available raw materials, and the method also has the advantages of mild reaction conditions, no byproducts in the process, high conversionrate and low production cost. The content of normal bodies can reach 98% or more.

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.

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

N-Heterocyclic carbene-mediated redox condensation of alcohols

N-Heterocyclic carbenes (NHCs) with a variety of oxidants promote the Mitsunobu-type coupling reactions of alcohols with phenols, carboxylic acids, and phthalimide. Experiments using a chiral alcohol indicate that these reactions proceed via SN1 or SN2 pathways depending on the polarity of the used solvents. The NHCs are consumed as reducing reagents to form their oxides as readily separable byproducts.

Synthesis of Amides and Phthalimides via a Palladium Catalyzed Aminocarbonylation of Aryl Halides with Formic Acid and Carbodiimides

A novel method for the preparation of amides and phthalimides has been developed. The process involves a palladium catalyzed aminocarbonylation of an aryl halide, using a carbodiimide and formic acid as the carbonyl source. Experimental data suggest that the mechanistic pathway for this process involves in-situ generation of carbon monoxide from the reaction of formic acid with a carbodiimide in the presence of a palladium catalyst. The method can be used to produce a variety of amides and N-substituted phthalimides efficiently.

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.