39739-01-0

Basic information

• Product Name: methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate
• Synonyms: 2H-isoindole-2-propanoic acid, 1,3-dihydro-1,3-dioxo-, methyl ester
• CAS NO: 39739-01-0
• Molecular Formula: C₁₂H₁₁NO₄
• Molecular Weight: 233.22
• Mol File: 39739-01-0.mol

Chemical Properties

• Boiling Point: 367.5°C at 760 mmHg
• Flash Point: 176.1°C
• Density: 1.32g/cm³
• Vapor Pressure: 1.36E-05mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate(39739-01-0)
• EPA Substance Registry System: methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate(39739-01-0)

Safety Data

• Hazardous Substances Data: 39739-01-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate is used as a synthetic intermediate for the development of drugs. Its unique structural properties and reactivity make it a valuable component in the creation of new pharmaceutical compounds.
Used in Agrochemical Industry:
In the agrochemical field, methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate is utilized as a building block for the synthesis of agrochemicals. Its potential applications in this industry contribute to the development of innovative products for agricultural use.
Used in Materials Science:
Methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate is employed in the field of materials science as a precursor for the synthesis of novel polymers and materials. Its incorporation into these materials allows for the creation of products with specific properties tailored for various applications.

Upstream product

• 136918-14-4 phthalimide 
• 292638-85-8 acrylic acid methyl ester 
• 67-56-1 methanol 
• 3485-84-5 N-vinylphthalimide 
• 201230-82-2 carbon monoxide 
• 3339-73-9 3-phthalimidopropanoic acid 
• 64-18-6 formic acid 
• 50-00-0 formaldehyd 
• 107-31-3 Methyl formate 
• 95349-09-0 vinyl β-phthalimidopropionate 

Downstream Products

• 3339-73-9 3-phthalimidopropanoic acid 
• 107-95-9 3-amino propanoic acid 

Relevant articles and documents

A convergent route to functional protected amines, diamines, and β-amino acids

Phthalimide protected amines react with NBS under peroxide initiation to give geminal phthalimido-bromo derivatives, which are readily converted into the corresponding xanthates. These xanthates in turn undergo radical additions to numerous olefins, provi

Preparation method of carboxylic ester compound

The invention relates to a preparation method of a carboxylic ester compound, which comprises the following steps: reacting carboxylic acid with methanol in air under the catalysis of nitrite to obtain an ester compound, the preparation method disclosed by the invention has the advantages of rich raw material sources, cheap and easily available catalyst, mild reaction conditions, simplicity and convenience in operation and the like, a series of fatty carboxylic acids can be modified with high yield, and particularly, the traditional esterification method is generally not suitable for esterification of drug molecules. By utilizing the method, a series of known drug molecules can be modified, so that a shortcut is provided for discovering new drug molecules.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

Oxidative damage of proline residues by nitrate radicals (NO3): A kinetic and product study

Tertiary amides, such as in N-acylated proline or N-methyl glycine residues, react rapidly with nitrate radicals (NO3) with absolute rate coefficients in the range of 4-7 × 108 M-1 s-1 in acetonitrile. The major pathway proceeds through oxidative electron transfer (ET) at nitrogen, whereas hydrogen abstraction is only a minor contributor under these conditions. However, steric hindrance at the amide, for example by alkyl side chains at the α-carbon, lowers the rate coefficient by up to 75%, indicating that NO3-induced oxidation of amide bonds proceeds through initial formation of a charge transfer complex. Furthermore, the rate of oxidative damage of proline and N-methyl glycine is significantly influenced by its position in a peptide. Thus, neighbouring peptide bonds, particularly in the N-direction, reduce the electron density at the tertiary amide, which slows down the rate of ET by up to one order of magnitude. The results from these model studies suggest that the susceptibility of proline residues in peptides to radical-induced oxidative damage should be considerably reduced, compared with the single amino acid.

A general platinum-catalyzed alkoxycarbonylation of olefins

Hydroxy- and alkoxycarbonylation reactions constitute important industrial processes in homogeneous catalysis. Nowadays, palladium complexes constitute state-of-the-art catalysts for these transformations. Herein, we report the first efficient platinum-catalysed alkoxycarbonylations of olefins including sterically hindered and functionalized ones. This atom-efficient catalytic transformation provides straightforward access to a variety of valuable esters in good to excellent yields and often with high selectivities. In kinetic experiments the activities of Pd- and Pt-based catalysts were compared. Even at low catalyst loading, Pt shows high catalytic activity.

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.

Development of efficient palladium catalysts for alkoxycarbonylation of alkenes

Herein, we report a general and efficient Pd-catalysed alkoxycarbonylation of sterically hindered and demanding olefins including a variety of tri-, tetra-substituted and 1,1-disubstituted alkenes. In the presence of 1,3-bis(tert-butyl(pyridin-2-yl)phosphanyl)propane L3 or 1,4-bis(tert-butyl(pyridin-2-yl)phosphanyl)butane L4 the desired esters are obtained in good yields and selectivities. Similar transformation is obtained using tertiary ether as showcased in the carbonylation of MTBE to the corresponding linear ester in high yield and selectivity.

A recyclable CO surrogate in regioselective alkoxycarbonylation of alkenes: Indirect use of carbon dioxide

Herein, we report a Pd-catalysed alkoxycarbonylation of alkenes based on the use of a recyclable CO2 reduction product, the crystalline and air-stable N-formylsaccharin, as a CO surrogate. The carbonylation proceeds under ambient conditions in an exceptionally complementary regioselective fashion yielding the desired branched products from styrene derivatives and valuable linear esters from alkyl-substituted alkenes.

Regioselective Pd-Catalyzed Methoxycarbonylation of Alkenes Using both Paraformaldehyde and Methanol as CO Surrogates

In recent years, considerable effort has focused on the development of novel carbonylative transformations using CO surrogates. Consequently, toxic CO gas can be replaced by more convenient inorganic or organic carbonyl compounds. Herein, the first regioselective methoxycarbonylation of alkenes with paraformaldehyde and methanol as CO substitutes is reported. This new procedure is applicable to a series of alkenes in the presence of a palladium catalyst under relatively mild conditions and is highly atom efficient.

PROCESS FOR PREPARING ESTERS FROM FORMATES AND OLEFINICALLY UNSATURATED COMPOUNDS

The invention provides a process for preparing esters from formates and olefinically unsaturated compounds with catalysts based on palladium compounds. In addition, the invention discloses a polyphasic reaction mixture and nonyl methyl ester mixtures prepared by the process according to the invention.