66917-06-4

Basic information

• Product Name: 2-(4-azidobutyl)-1H-isoindole-1,3(2H)-dione
• CAS NO: 66917-06-4
• Molecular Formula: C₁₂H₁₂N₄O₂
• Molecular Weight: 244.2493
• Mol File: 66917-06-4.mol

Chemical Properties

• CAS DataBase Reference: 2-(4-azidobutyl)-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-azidobutyl)-1H-isoindole-1,3(2H)-dione(66917-06-4)
• EPA Substance Registry System: 2-(4-azidobutyl)-1H-isoindole-1,3(2H)-dione(66917-06-4)

Safety Data

• Hazardous Substances Data: 66917-06-4(Hazardous Substances Data)

Usage

Derivative of isoindole-1,3(2H)-dione

A heterocyclic compound The compound is based on the structure of isoindole-1,3(2H)-dione, which is a heterocyclic compound containing both carbon and nitrogen atoms in its ring.

Azide group

High reactivity The compound contains an azide group (N3), which is known for its high reactivity and can participate in various chemical reactions.

Butyl chain

Attached to the isoindole ring A butyl chain (C4H9) is attached to the isoindole ring, adding more complexity to the compound's structure.

Click chemistry

Synthesis of complex organic molecules The azide group in the compound can be used in click chemistry reactions, which are efficient and selective methods for synthesizing complex organic molecules.

Versatile building block

Organic synthesis Isoindole-1,3(2H)-diones, like the base compound, are used as versatile building blocks in organic synthesis for creating various functionalized molecules.

Potential applications

Chemical modifications and synthetic transformations The presence of both the azide group and the butyl chain makes 2-(4-azidobutyl)-1H-isoindole-1,3(2H)-dione a potentially useful compound for chemical modifications and synthetic transformations in various applications.

Upstream product

• 5394-18-3 2-(4-bromobutyl)isoindoline-1,3-dione 
• 42152-99-8 2-(4-chlorobutyl)isoindoline-1,3-dione 
• 1074-82-4 potassium phtalimide 
• 52898-32-5 N-(3-butenyl)phthalimide 
• 671821-46-8 1-azido-4-chloro-butane 

Downstream Products

• 1391026-16-6 (1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-1H-1,2,3-triazol-4-yl)methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate 
• 1391026-06-4 (1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-1H-1,2,3-triazol-4-yl)methyl 5-methyl-3-phenylisoxazole-4-3-carboxylate 
• 1391026-11-1 (1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-1H-1,2,3-triazol-4-yl)methyl 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylate 
• 1391026-21-3 (1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-1H-1,2,3-triazol-4-yl)methyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylate 
• 1605324-41-1 2-(4-(4-butyl-5-(phenylthio)-1H-1,2,3-triazol-1-yl)butyl)isoindoline-1,3-dione 
• 88192-20-5 4-azidobutan-1-amine 
• 1267640-80-1 4-azidobutan-1-amine hydrochloride 

Relevant articles and documents

Design and synthesis of a bis-macrocyclic host and guests as building blocks for small molecular knots

The thread-link-cut (TLC) approach has previously shown promise as a novel method to synthesize molecular knots. The modular second-generation approach to small trefoil knots described herein involves electrostatic interactions between an electron-rich bismacrocyclic host compound and electron-deficient guests in the threading step. The bis-macrocyclic host was synthesized in eight steps and 6.6% overall yield. Ammonium and pyridinium guests were synthesized in 4-5 steps. The TLC knot-forming sequence was carried out and produced a product with the expected molecular weight, but, unfortunately, further characterization did not produce conclusive results regarding the topology of the product.

ENVIRONMENTALLY-FRIENDLY HYDROAZIDATION OF OLEFINS

The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.

Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins

We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.

Copper-catalyzed cascade click/nucleophilic substitution reaction to access fully substituted triazolyl-organosulfurs

A novel cascade click/nucleophilic substitution reaction is developed to access 4-heterofunctionalized fully substituted triazolyl-organosulfurs using thiocyanates as both leaving groups and organosulfur precursors. This method features high regioselectivities and board substrate scope. 33 examples are shown to demonstrate the structural diversity through the synthesis of fully substituted triazolyl-organosulfurs including triazolyl-thiocyanates, triazolyl-sulfinylcyanides, triazolyl-thioethers, triazolyl-thiols and triazolyl-disulfides from internal thiocyanatoalkynes.

Traceless Templated Amide-Forming Ligations

Template assistance allows organic reactions to occur under highly dilute conditions - where intermolecular reactions often fail to proceed - by bringing reactants into close spatial proximity. This strategy has been elegantly applied to numerous systems, but always with the retention of at least one of the templating groups in the product. In this report, we describe a traceless, templated amide-forming ligation that proceeds at low micromolar concentration under aqueous conditions in the presence of biomolecules. We utilized the unique features of an acylboronate-hydroxylamine ligation, in which covalent bonds are broken in each of the reactants as the new amide bond is formed. By using streptavidin as a template and acylboronates and O-acylhydroxylamines bearing desthiobiotins that are cleaved upon amide formation, we demonstrate that traceless, templated ligation occurs rapidly even at submicromolar concentrations. The requirement for a close spatial orientation of the functional groups - achieved upon binding to streptavidin - is critical for the observed enhancement in the rate and quantity of product formed.

Rhodium(I)-Catalyzed Regioselective Azide-internal Alkynyl Trifluoromethyl Sulfide Cycloaddition and Azide-internal Thioalkyne Cycloaddition under Mild Conditions

A regioselective method to access fully substituted 5-trifluoromethylthio-1,2,3-triazoles and 5-thio-1,2,3-triazoles from the internal alkynyl trifluoromethyl sulfides and internal thioalkynes by a rhodium(I)-catalyzed azide-alkyne cycloaddition (RhAAC) reaction under mild conditions has been developed. This approach features good compatibility with water and air, a broad substrate scope, good functional group tolerance, high yields and excellent regioselectivities. The high 1,5-regioselectivities were controlled by the strong coordination between the sulfur atom and the π-acidic rhodium. The advantages of this method further include its applicability to gram-scale preparation, the use of solid-phase synthesis technique, and the mutually orthogonal CuAAC-RhAAC reaction. (Figure presented.).

Design and Synthesis of Triazole-Phthalimide Hybrids with Anti-inflammatory Activity

Phthalimido-alkyl-1H-1,2,3-triazole derivatives 3a–d and 4a–d were efficiently synthesized using 1,3-di-polar cycloaddition reaction. Anti-inflammatory activity and toxicity studies were performed. The results demonstrated that all the tested compounds reduced carrageenan-induced paw edema and indicated no lethality for toxicity against Artemia salina and acute toxicity in vivo (LD50 up to 1gkg ?1). Furthermore, the structure of phthalimide linked to phenyl group proved to be more active than the compounds containing benzothiazole moiety. Structural modifications such as removal of the phthalimide group and subsequent acetylation, to exemplify a non-cyclic amide, demonstrate that the phthalimide and triazole moieties are important for design of potent candidates with anti-inflammatory drug proprieties. Docking into the cyclooxy-genase-2 (COX-2) confirms the importance of the phthalimide and triazole groups in the anti-inflammatory activity. The histopathological studies showed that the compounds 3a–d and 4a–d did not cause serious pathological lesions liver or kidneys.

Palladium-Catalyzed Annulation of Aryltriazoles and Arylisoxazoles with Alkynes

We developed herein a palladium-catalyzed annulation of aryltriazoles and arylisoxazoles with internal alkynes via C?H bond activation process. 4,5-disubstituted-3H-naphtho[1,2-d][1,2,3]triazoles and 4,5-disubstituted-naphtho[2,1-d]isoxazoles could be afforded in good yields, respectively. The starting materials are readily available and the scope and applications of this transformation were explored. The reaction offers a practical approach to naphthalene fused heterocycles. (Figure presented.).

Chemically Induced Degradation of Sirtuin 2 (Sirt2) by a Proteolysis Targeting Chimera (PROTAC) Based on Sirtuin Rearranging Ligands (SirReals)

Here we report the development of a proteolysis targeting chimera (PROTAC) based on the combination of the unique features of the sirtuin rearranging ligands (SirReals) as highly potent and isotype-selective Sirt2 inhibitors with thalidomide, a bona fide

Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) of Internal Alkynylphosphonates with High Regioselectivities under Mild Conditions

A regioselective method to access fully substituted 1,2,3-triazolyl-4-phosphonates from the internal alkynylphosphonates by rhodium(I)-catalyzed azide-alkyne cycloaddition (RhAAC) under mild conditions is reported. This approach is water and air compatible and has a broad substrate scope, good functional group tolerance, high yields and excellent regioselectivities. Fully substituted 1,2,3-triazolyl-4-phosphonates are directly prepared from the internal alkynylphosphonates by RhAAC with high 1,4-regioselectivities. The gram-scale preparation, application to carbohydrate synthesis and the solid-phase synthesis of triazolyl-4-phosphonates are highlights of this method. (Figure presented.).