20919-42-0

Basic information

• Product Name: 2-iodo-1H-isoindole-1,3(2H)-dione
• Synonyms: 1H-isoindole-1,3(2H)-dione, 2-iodo-; 2-Iodo-1H-isoindole-1,3(2H)-dione
• CAS NO: 20919-42-0
• Molecular Formula: C₈H₄INO₂
• Molecular Weight: 273.0273
• Mol File: 20919-42-0.mol

Chemical Properties

• Boiling Point: 355.7°C at 760 mmHg
• Flash Point: 168.9°C
• Density: 2.19g/cm³
• Vapor Pressure: 3.08E-05mmHg at 25°C
• Refractive Index: 1.754
• CAS DataBase Reference: 2-iodo-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-iodo-1H-isoindole-1,3(2H)-dione(20919-42-0)
• EPA Substance Registry System: 2-iodo-1H-isoindole-1,3(2H)-dione(20919-42-0)

Safety Data

• Hazardous Substances Data: 20919-42-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-iodo-1H-isoindole-1,3(2H)-dione is used as a building block for the synthesis of complex organic molecules, which can be further utilized in the development of new pharmaceutical compounds. Its unique structure and reactivity contribute to the creation of novel drug candidates with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 2-iodo-1H-isoindole-1,3(2H)-dione serves as a versatile reagent that can participate in various chemical reactions. Its iodine atom and other functional groups enable it to undergo a range of transformations, making it a valuable tool for the synthesis of diverse organic compounds.
Used in Chemical Research:
2-iodo-1H-isoindole-1,3(2H)-dione is also employed in chemical research as a model compound to study the reactivity and properties of similar structures. Its unique features provide insights into the behavior of related compounds and contribute to the advancement of synthetic chemistry.

Upstream product

• 136918-14-4 phthalimide 
• 86451-26-5 2,2'-(phenyl-λ³-iodanediyl)bis(isoindoline-1,3-dione) 
• 1875-48-5 N-aminophthalamide 
• 1074-82-4 potassium phtalimide 
• 7553-56-2 iodine 
• 33081-78-6 sodium phthalimide 
• 7782-50-5 chlorine 
• 7726-95-6 bromine 

Downstream Products

• 550-44-7 N-methylphthalimide 
• 719-98-2 N-((trifluoromethyl)thio)isoindoline-1,3-dione 
• 520-03-6 N-phenylphthalimide 

Relevant articles and documents

Aliphatic C-H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical

Contrary to C-H chlorination and bromination, the direct iodination of alkanes represents a great challenge. We reveal a new N-iodoamide that is capable of a direct and efficient C-H bond iodination of various cyclic and acyclic alkanes providing iodoalkanes in good yields. This is the first use of N-iodoamide for C-H bond iodination. The method also works well for benzylic C-H bonds, thereby constituting the missing version of the Wohl-Ziegler iodination reaction. Mechanistic details were elucidated by DFT computations, and the N-centered radical derived from the used N-iodoamide, which is the key intermediate in this process, was matrix-isolated in a solid argon matrix and characterized by UV-vis as well as IR spectroscopy.

Zinc-catalyzed selective reduction of cyclic imides with hydrosilanes: Synthesis of ω-hydroxylactams

Cyclic imides were selectively reduced to the corresponding ω-hydroxylactams in high yields with (EtO)3SiH (triethoxysilane) or PMHS (polymethylhydrosiloxane) under catalysis of zinc diacetate dehydrate [Zn(OAc)2 2H2O] (10%) and tetramethylethylenediamine (TMEDA) (10%). This catalytic protocol showed good functional group tolerance as well as excellent regioselectivity for unsymmetrical imides bearing coordinating groups adjacent to the carbonyl.

PROCESS FOR THE PREPARATION OF N-IODOAMIDES

The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.

TIN(IV) MEDIATED SYNTHESIS OF N-HALO COMPOUNDS

Some representative N-halo compounds like N-bromosuccinimide, N-iodosuccinimide, N-bromophthalimide, N-iodophthalimide, N-iodobenzimidazole and N-iodobenzotriazole have been synthesised in good yields under neutral and mild conditions via an intermediate formed from the parent NH species and bis(tri-n-butyltin) oxide.The tin oxide is recovered as recyclable tri-n-butyltin halide.