1312703-28-8

Basic information

• Product Name: 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylic acid
• Synonyms: 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylic acid
• CAS NO: 1312703-28-8
• Molecular Weight: 333.343
• Mol File: 1312703-28-8.mol

Chemical Properties

• Melting Point: 349 °C (decomp)
• Boiling Point: 632.5±55.0 °C(Predicted)
• Density: 1.347±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylic acid(1312703-28-8)
• EPA Substance Registry System: 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylic acid(1312703-28-8)

Safety Data

• Hazardous Substances Data: 1312703-28-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylic acid is used as a building block for the synthesis of larger molecules, leveraging its complex molecular structure and reactivity to create a variety of organic compounds.
Used in Materials Science:
In the field of materials science, 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylic acid is utilized for its potential applications in developing new materials with unique properties, thanks to its structural characteristics.
Used in Pharmaceutical Industry:
2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylic acid is used as a valuable intermediate in the production of pharmaceuticals, contributing to the development of new drugs and therapeutic agents due to its chemical versatility and functional groups.
Used in Other Industries:
2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylic acid may also find applications in various other industries where its unique structure and reactivity can be harnessed for the creation of specialized organic compounds or materials.

Upstream product

• 1312703-30-2 dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate 
• 3638-73-1 2,5-dibromoaniline 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 

Relevant articles and documents

A metal-organic framework containing unusual eight-connected Zr-oxo secondary building units and orthogonal carboxylic acids for ultra-sensitive metal detection

Two metal-organic frameworks (MOFs) with Zr-oxo secondary building units (SBUs) were prepared by using p,p′-terphenyldicarboxylate (TPDC) bridging ligands pre-functionalized with orthogonal succinic acid (MOF-1) and maleic acid groups (MOF-2). Single-crystal X-ray structure analysis of MOF-1 provides the first direct evidence for eight-connected SBUs in UiO-type MOFs. In contrast, MOF-2 contains twelve-connected SBUs as seen in the traditional UiO MOF topology. These structural assignments were confirmed by extended X-ray absorption fine structure (EXAFS) analysis. The highly porous MOF-1 is an excellent fluorescence sensor for metal ions with the detection limit of 2+and three to four orders of magnitude greater sensitivity for metal ions than previously reported luminescent MOFs.

Nanoscale metal-organic frameworks for the co-delivery of cisplatin and pooled siRNAs to enhance therapeutic efficacy in drug-resistant ovarian cancer cells

Ovarian cancer is the leading cause of death among women with gynecological malignancies. Acquired resistance to chemotherapy is a major limitation for ovarian cancer treatment. We report here the first use of nanoscale metal-organic frameworks (NMOFs) for the co-delivery of cisplatin and pooled small interfering RNAs (siRNAs) to enhance therapeutic efficacy by silencing multiple drug resistance (MDR) genes and resensitizing resistant ovarian cancer cells to cisplatin treatment. UiO NMOFs with hexagonal-plate morphologies were loaded with a cisplatin prodrug and MDR gene-silencing siRNAs (Bcl-2, P-glycoprotein [P-gp], and survivin) via encapsulation and surface coordination, respectively. NMOFs protect siRNAs from nuclease degradation, enhance siRNA cellular uptake, and promote siRNA escape from endosomes to silence MDR genes in cisplatin-resistant ovarian cancer cells. Co-delivery of cisplatin and siRNAs with NMOFs led to an order of magnitude enhancement in chemotherapeutic efficacy in vitro, as indicated by cell viability assay, DNA laddering, and Annexin V staining. This work shows that NMOFs hold great promise in the co-delivery of multiple therapeutics for effective treatment of drug-resistant cancers.

Pd(0)@UiO-68-AP: Chelation-directed bifunctional heterogeneous catalyst for stepwise organic transformations

A bifunctional heterogeneous catalyst Pd(0)@UiO-68-AP based on a chelation-directed post-synthetic approach is reported. It exhibits typical heterogeneous catalytic behaviour and can promote benzyl alcohol oxidiation-Knoevenagel condensation in a stepwise way.

Modulated synthesis of Zr-based metal-organic frameworks: From nano to single crystals

We present an investigation on the influence of benzoic acid, acetic acid, and water on the syntheses of the Zr-based metal-organic frameworks Zr-bdc (UiO-66), Zr-bdc-NH2 (UiO- 66-NH2), Zr-bpdc (UiO-67), and Zr- tpdc-NH2 (UiO-68-NH2) (H2bdc: terephthalic acid, H2bpdc: biphenyl-4,4'- dicarboxylic acid, H2tpdc: terphenyl- 4,4"-dicarboxylic acid). By varying the amount of benzoic or acetic acid, the synthesis of Zr-bdc can be modulated. With increasing concentration of the modulator, the products change from intergrown to individual crystals, the size of which can be tuned. Addition of benzoic acid also affects the size and morphology of Zr-bpdc and, additionally, makes the synthesis of Zr-bpdc highly reproducible. The control of crystal and particle size is proven by powder XRD, SEM and dynamic light scattering (DLS) measurements. Thermogravimetric analysis (TGA) and Ar sorption experiments show that the materials from modulated syntheses can be activated and that they exhibit high specific surface areas. Water proved to be essential for the formation of well-ordered Zr-bdc-NH2. Zr- tpdc-NH2, a material with a structure analogous to that of Zr-bdc and Zr- bpdc, but with the longer, functionalized linker 2'-amino-1,1':4',1"-terphenyl- 4,4"-dicarboxylic acid, was obtained as single crystals. This allowed the first single-crystal structural analysis of a Zr-based metal-organic framework. Copyright

Different functional group modified zirconium frameworks for the photocatalytic reduction of carbon dioxide

Conversion of carbon dioxide (CO2) into useful chemicals is an important and urgent task from the energy and environment perspective. Herein, through a post-synthetic modification (PSM) approach, we synthesized three new metal-organic frameworks (MOFs) UiO-68-PSMs with different functional groups, namely, UiO-68-F, UiO-68-CH3 and UiO-68-OCH3, for the photocatalytic reduction of CO2. By introducing electron-withdrawing and electron-donating groups, UiO-68-PSMs showed different performance for the selective photocatalytic reduction of CO2 to CO because of change in charge separation and band gap of UiO caused by the presence of different functional groups.

Stepwise ligand exchange for the preparation of a family of mesoporous MOFs

A stepwise ligand exchange strategy is utilized to prepare a series of isoreticular bio-MOF-100 analogues. Specifically, in situ ligand exchange with progressively longer dicarboxylate linkers is performed on single crystalline starting materials to synthesize products with progressively larger mesoporous cavities. The new members of this series of materials, bio-MOFs 101-103, each exhibit permanent mesoporosity and pore sizes ranging from ～2.1-2.9 nm and surface areas ranging from 2704 to 4410 m2/g. The pore volume for bio-MOF 101 is 2.83 cc/g. Bio-MOF-102 and 103 have pore volumes of 4.36 and 4.13 cc/g, respectively. Collectively, these data establish this unique family of MOFs as one of the most porous reported to date.

Amino Acid-Functionalized Metal-Organic Frameworks for Asymmetric Base–Metal Catalysis

We report a strategy to develop heterogeneous single-site enantioselective catalysts based on naturally occurring amino acids and earth-abundant metals for eco-friendly asymmetric catalysis. The grafting of amino acids within the pores of a metal-organic framework (MOF), followed by post-synthetic metalation with iron precursor, affords highly active and enantioselective (>99 % ee for 10 examples) catalysts for hydrosilylation and hydroboration of carbonyl compounds. Impressively, the MOF-Fe catalyst displayed high turnover numbers of up to 10 000 and was recycled and reused more than 15 times without diminishing the enantioselectivity. MOF-Fe displayed much higher activity and enantioselectivity than its homogeneous control catalyst, likely due to the formation of robust single-site catalyst in the MOF through site-isolation.

Zirconium-based MOF catalyst with double active sites and preparation method and application thereof

The invention discloses a zirconium-based MOF catalyst loaded with double active sites as well as a preparation method and an application of the zirconium-based MOF catalyst. The method comprises thefollowing steps: adding zirconium salt and an organic ligand into an organic solvent, taking organic acid as a regulator, and carrying out self-assembly reaction to obtain a metal organic framework; adding salicylaldehyde for aldehyde amine condensation to obtain chelating coordination sites, adding palladium salt, and performing coordination through an impregnation method; reducing the obtained MOF in hydrogen to obtain an MOF loaded with Pd nanoparticles; reacting MOF and zinc salt in an organic solvent, and obtaining the catalyst. The Pd-Zn-coated UiO-68-NH2-CH3 catalyst synthesized by thepreparation method disclosed by the invention has efficient catalytic activity in a tandem alcohol oxidation/aldehyde cyanosilylation reaction. According to the catalyst, a metal organic framework UiO-68-NH2-CH3 is constructed, Pd nanoparticles and Zn are loaded by taking the metal organic framework UiO-68-NH2-CH3 as a carrier, the loading capacity of the Pd nanoparticles is 4-8wt%, and the loading capacity of the Zn is 3-5wt%.

Metal-organic frameworks containing nitrogen-donor ligands for efficient catalytic organic transformations

Metal-organic framework (MOFs) compositions based on nitrogen donor-based organic bridging ligands, including ligands based on 1,3-diketimine (NacNac), bipyridines and salicylaldimine, were synthesized and then post-synthetically metalated with metal precursors, such as complexes of first row transition metals. Metal complexes of the organic bridging ligands could also be directly incorporated into the MOFs. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.

Single-Site Cobalt-Catalyst Ligated with Pyridylimine-Functionalized Metal-Organic Frameworks for Arene and Benzylic Borylation

We report a highly active single-site heterogeneous cobalt-catalyst based on a porous and robust pyridylimine-functionalized metal-organic frameworks (pyrim-MOF) for chemoselective borylation of arene and benzylic C-H bonds. The pyrim-MOF having UiO-68 topology, constructed from zirconium-cluster secondary building units and pyridylimine-functionalized dicarboxylate bridging linkers, was metalated with CoCl2 followed by treatment of NaEt3BH to give the cobalt-functionalized MOF-catalyst (pyrim-MOF-Co). Pyrim-MOF-Co has a broad substrate scope, allowing the C-H borylation of halogen-, alkoxy-, alkyl-substituted arenes as well as heterocyclic ring systems using B2pin2 or HBpin (pin = pinacolate) as the borylating agent to afford the corresponding arene- or alkyl-boronate esters in good yields. Pyrim-MOF-Co gave a turnover number (TON) of up to 2500 and could be recycled and reused at least 9 times. Pyrim-MOF-Co was also significantly more robust and active than its homogeneous control, highlighting the beneficial effect of active-site isolation within the MOF framework that prevents intermolecular decomposition. The experimental and computational studies suggested (pyrim?-)CoI(THF) as the active catalytic species within the MOF, which undergoes a mechanistic pathway of oxidative addition, turnover limiting σ-bond metathesis, followed by reductive elimination to afford the boronate ester.