945865-80-5

Usage

Main Properties

1. Chemical Classification: Aldehyde derivative
2. Functional Groups:
Dioxaborolane moiety (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl))
Isophthalaldehyde group
3. Application Fields: Organic synthesis, materials science
4. Utility: Building block for various organic molecules
5. Reactivity: Valuable tool in organic chemistry research
6. Versatility: Suitable for pharmaceutical and advanced materials synthesis
7. Reagent Role: Participates in Suzuki-Miyaura cross-coupling reaction
8. Carbon-Carbon Bond Formation: Facilitates the creation of carbon-carbon bonds

Composition

Contains aldehyde, dioxaborolane, and isophthalaldehyde groups

Synthesis Use

Employed as a building block in various organic molecule syntheses

Functional Group Role

The dioxaborolane moiety enhances reactivity and versatility

Suzuki-Miyaura Reaction

Reacts as a reagent in the Suzuki-Miyaura cross-coupling reaction

Value

Valuable in pharmaceutical and advanced material synthesis

Contributions

Aids in the formation of carbon-carbon bonds, crucial in organic chemistry

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalaldehyde's combination of functional groups and its reactivity in key organic reactions make it indispensable in diverse synthetic applications, particularly in the creation of complex organic molecules and materials.

Upstream product

• 480424-62-2 (3,5-diformylphenyl)boronic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 626-19-7 Isophthalaldehyde 
• 120173-41-3 5-bromobenzene-1,3-dicarbaldehyde 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 2459652-59-4 C₂₈H₁₈O₄ 
• 150443-85-9 [1,1'-biphenyl]-3,3',5,5'-tetracarbaldehyde 

Relevant academic research and scientific papers

Synthesis of an Fe(terpy-cage)2dumbbell

An azide masked amine is used to obtain a cage of lower symmetry that possess one terpy-group in an exo-position. This group can coordinate to iron(ii), yielding selectively an easy to purify Fe(terpy-cage)2 dumbbell. The dumbbell can also be obtained in a one pot reaction, which proceeded without isolation of the exo-functionalized cage.

Imine organic cages derived from tetraphenylethylene dialdehydes exhibiting aggregation-induced emission and explosives detection

Sensitive detection of explosives has always been a frontier research for scientists. In this work, two [3 + 2] imine organic cages (1 and 2) stemmed from distinct TPE-based dialdehydes (TPE-2CHO/TPE-2PCHO) and common tri(2-aminoethyl)amine were obtained. Both of them are fluorescence silence in solution and high-efficient AIE could be observed, which is different from all known TPE-based organic cages with AIEE properties. Because of the cage skeleton encircled by multiple benzene rings, the two cages can effectively detect various explosives including nitrobenzene, 2-nitrotoluene, 3-nitrotoluene, 4-nitrotoluene and 2,6-dinitrotoluene both in solution and in the solid state, in which cage 1 displays higher detection ability due to its nine encircling benzene donors

Inducing Social Self-Sorting in Organic Cages To Tune The Shape of The Internal Cavity

Many interesting target guest molecules have low symmetry, yet most methods for synthesising hosts result in highly symmetrical capsules. Methods of generating lower symmetry pores are thus required to maximise the binding affinity in host–guest complexes. Herein, we use mixtures of tetraaldehyde building blocks with cyclohexanediamine to access low-symmetry imine cages. Whether a low-energy cage is isolated can be correctly predicted from the thermodynamic preference observed in computational models. The stability of the observed structures depends on the geometrical match of the aldehyde building blocks. One bent aldehyde stands out as unable to assemble into high-symmetry cages-and the same aldehyde generates low-symmetry socially self-sorted cages when combined with a linear aldehyde. We exploit this finding to synthesise a family of low-symmetry cages containing heteroatoms, illustrating that pores of varying geometries and surface chemistries may be reliably accessed through computational prediction and self-sorting.

Reversible Multistimuli Switching of a Spiropyran-Functionalized Organic Cage in Solid and Solution

A spiropyran-decorated covalent organic cage (PC2) has been designed, employing dynamic imine chemistry followed by imine bond reduction. The molecule is capable of altering its color upon exposure to external stimuli such as heat and light. Construction of a 3D organic cage introduces a new piece to the system by swapping the closed form with the open form in the solid state with diverse color change. Moreover, this material has high chemical stability and is capable of reversible stimuli-responsive color change without any degradation for an extended period.

Regioselective 15-bromination and functionalization of a stable synthetic bacteriochlorin

(Chemical Equation Presented) 5-Methoxy-8,8,18,18-tetramethyl-2,12-di-p- tolylbacteriochlorin (MeO-BC) undergoes regioselective electrophilic bromination with NBS to give the 15-bromo analogue (MeO-BC-Br15) in 85% yield. By contrast, the bacter