148332-32-5

Basic information

• Product Name: 2,2':6',2''-Terpyridine-4'-methanol
• Synonyms: 2,2':6',2''-Terpyridine-4'-methanol;2,2':6',2''-Terpyridine-4'-methano
• CAS NO: 148332-32-5
• Molecular Formula: C₁₆H₁₃N₃O
• Molecular Weight: 263.29392
• EINECS: -0
• Mol File: 148332-32-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 462.2±40.0 °C(Predicted)
• Appearance: /
• Density: 1.233±0.06 g/cm3(Predicted)
• PKA: 12.77±0.10(Predicted)
• CAS DataBase Reference: 2,2':6',2''-Terpyridine-4'-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2':6',2''-Terpyridine-4'-methanol(148332-32-5)
• EPA Substance Registry System: 2,2':6',2''-Terpyridine-4'-methanol(148332-32-5)

Safety Data

• Hazardous Substances Data: 148332-32-5(Hazardous Substances Data)

Usage

General Description

2,2':6',2''-Terpyridine-4'-methanol is a chemical compound with the molecular formula C19H16N2O. It belongs to the class of terpyridine derivatives, which are widely used in various fields including coordination chemistry, material science, and medicinal chemistry. 2,2':6',2''-Terpyridine-4'-methanol is a derivative of 2,2':6',2''-terpyridine with an additional hydroxyl group attached to the 4' position of one of the pyridine rings. The presence of the hydroxyl group can significantly alter the chemical properties and reactivity of the parent terpyridine compound. 2,2':6',2''-Terpyridine-4'-methanol has potential applications as a ligand in coordination chemistry and as a building block for the synthesis of advanced materials and pharmaceuticals. Its unique structure and properties make it a valuable and versatile compound for diverse scientific and industrial applications.

Upstream product

• 148332-36-9 [2,2′:6′,2′′-terpyridine]-4′-carboxylic acid 
• 247058-06-6 2,2'-6',2''-terpyridine-4'-carboxylic acid methyl ester 
• 108295-45-0 4′-formyl-2,2′:6′2″-terpyridine 

Relevant articles and documents

Live Cell Labeling with Terpyridine Derivative Proligands to Measure Cytotoxicity Mediated by Immune Cells

Immunotherapy using immune checkpoint inhibitors and CAR-T cells has revolutionized treatment for patients with malignant tumors. However, measuring tumor cell cytotoxicity mediated by immune effector cells in clinical laboratories has been difficult due to the requirement for radioactive substances. In this study, a series of novel terpyridine derivative proligands were synthesized, and a non-radioactive cellular cytotoxicity assay using the newly synthesized compounds was developed for use in preclinical and clinical studies for cancer immunotherapy. Once internalized into target cells, the compounds are hydrolyzed by esterases, resulting in the intracellular accumulation of the negatively charged terpyridine derivatives. When the labeled target cells are recognized and killed by immune effector cells, the integrity of the cell membrane is disrupted, and the terpyridine derivatives are released. Upon combining the culture supernatant with europium (Eu3+), the cytotoxicity of immune effector cells for the target cells can be quantitatively determined by measuring the intensity of the Eu3+/ligand-derived time-resolved fluorescence. Thus, the assay developed in this study would facilitate the development of novel cancer immunotherapies.

Bis(terpyridyl)-ruthenium(II) units attached to polyazacycloalkanes as sensing fluorescent receptors for transition metal ions

A synthetic strategy has been devised for the preparation of new compounds in which terpyridyl fragments are linked to 1,4,8,11- tetraazacyclotetradecane (cyclam). Reaction of excess cyclam with 4'-[(4- bromomethyl)phenyl]-2,2':2'',6'-terpyridine afforded the ligand 1-[4'-p- tolyl-(2,2':6',2''-terpyridyl)]-1,4,8,11-tetraazacyclotetradecane (L1) in which the tetraaza macrocycle was covalently attached to one benzylterpyridyl fragment. Under similar conditions reaction of cyclam with excess 4'-[(4- bromomethyl)phenyl]-2,2':2'',6'-terpyridine gave the tetra substituted cyclam derivative 1,4,8,11-[4'-p-tolyl-(2,2':6',2''-terpyridyl)]-1,4,8,11- tetraazacyclotetradecane (L2). The multidentate ligand L2 was crystallographically characterised by single-crystal X-ray diffraction techniques. Reaction of L1 with [Ru(mtpy)Cl3] gave the heteroleptic ruthenium(II) complex [Ru(L1)(mtpy)][PF6]2 (mtpy = 4'-methyl-2,2':6'2''- terpyridine). The fluorescent intensity of the metallo-receptor [Ru(L1)(mtpy)][PF6]2 was quenched selectively in the presence of copper(II) in an aqueous environment. To gain insight into the nature of this interaction, potentiometric titrations on [Ru(L1)(mtpy)]2+ in the presence of Cu2+ were carried out. The quenching of the emission intensity was associated with the presence of the copper {Cu[Ru(L1)(mtpy)]}4+ complex in solution. The receptor 1-[4'-methyl-(2,2':6',2''-terpyridyl)]-1,4,8,11- tetraazacyclotetradecane (L3), in which the cyclam fragment is separated from the terpyriyl by a methylene group, has also been synthesised by reaction of 4'-bromomethyl-2,2':2'',6'-terpyridine and cyclam. With L3 as starting material, the ruthenium complex [Ru(L3)(mtpy)]2+ was prepared in order to evaluate the effect that the nature of the spacer has on the quenching of the fluorescence upon addition of Cu2+.