4695-37-8

Basic information

• Product Name: (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid
• Synonyms: (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid; 2H-Isoindole-2-acetic acid, 1,3-dihydro-1,3-dioxo-alpha-phenyl-
• CAS NO: 4695-37-8
• Molecular Formula: C₁₆H₁₁NO₄
• Molecular Weight: 281.2628
• Mol File: 4695-37-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 480.8°C at 760 mmHg
• Flash Point: 244.6°C
• Density: 1.459g/cm³
• Vapor Pressure: 4.7E-10mmHg at 25°C
• Refractive Index: 1.681
• CAS DataBase Reference: (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid(4695-37-8)
• EPA Substance Registry System: (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid(4695-37-8)

Safety Data

• Hazardous Substances Data: 4695-37-8(Hazardous Substances Data)

Usage

General Description

(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid, also known as Isoindoline-1,3-dione, is a chemical compound with the molecular formula C15H11NO4. It is a derivative of isoindoline that contains a phenylacetic acid moiety. (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid is commonly used as a building block in organic synthesis and pharmaceutical development due to its unique structural and chemical properties. It has been studied for potential medicinal applications, such as anti-inflammatory and analgesic effects, making it a valuable target for drug discovery. Additionally, its versatile reactivity allows for the synthesis of diverse chemical compounds for various industrial and research purposes.

Upstream product

• 85-44-9 phthalic anhydride 
• 2835-06-5 phenylglycin 
• 16750-42-8 2-amino-2-phenylacetonitrile 
• 532-28-5 (RS)-mandelonitrile 

Downstream Products

• 174536-94-8 N-phthalyl (R,R)-phenylglycine pantolactonyl ester 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 

Relevant articles and documents

Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)-H Direct Fluorination

A coordinating, copper-catalyzed direct α-C(sp3)-H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable, single absolute configurations of the target compounds.

Design, synthesis and mechanism of novel shikonin derivatives as potent anticancer agents

In this study, a series of novel shikonin derivatives (30-49) were designed and synthesized and their anti-proliferative activities were evaluated against five different cancer cell lines, including HeLa, HepG2, MCF-7, BGC and A549. Some of the compounds show strong anti-proliferative effects against HeLa, HepG2 and MCF-7 with IC50 values ranging from 1.26 to 18.50 μM and show lower side effects towards normal cell lines as compared to shikonin. Compared to other compounds and shikonin itself, compound 40 displayed much stronger anti-proliferative effects against various cancer cell lines. Furthermore, the flow cytometry results demonstrated that compound 40 could obviously induce apoptosis in a dose- and time-dependent manner and also cause cell cycle arrest at the G2/M phase. For further investigation of the aforementioned mechanisms, we performed Western blot experiments and found that the cleavage of PARP and upstream caspase-3 increased; moreover, caspase-9 was activated by cleavage but not caspase-8. These aforementioned results also indicate that compound 40 could induce caspase-9 involved apoptosis and G2/M phase cell cycle arrest via the P21, p-CDC2 (Tyr15) pathway independent of P53.

Synthesis and alkaline hydrolysis of some N-substituted phthalimides.

-