133308-61-9

Basic information

• Product Name: 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride
• Synonyms: 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride
• CAS NO: 133308-61-9
• Molecular Weight: 232.669
• Mol File: 133308-61-9.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 380.2±42.0 °C(Predicted)
• Density: 1.265±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride(133308-61-9)
• EPA Substance Registry System: 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride(133308-61-9)

Safety Data

• Hazardous Substances Data: 133308-61-9(Hazardous Substances Data)

Usage

Description

4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride, also known as 4''-Methyl[2,2''-bipyridine]-4-carbonyl Chloride, is an organic compound with the molecular formula C11H8ClN. It is a derivative of bipyridine, featuring a methyl group at the 4' position and a carbonyl chloride group at the 4 position. 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride is characterized by its potential reactivity and utility in the synthesis of various complex molecules.

Uses

Used in Pharmaceutical Industry:
4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride is used as a synthetic intermediate for the preparation of aminophenylporphyrins, which are important compounds in the pharmaceutical industry. These porphyrins have potential applications in the development of drugs targeting various diseases, including cancer, due to their unique chemical and photophysical properties.
Used in Chemical Research:
In the field of chemical research, 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride serves as a valuable building block for the synthesis of novel bipyridine-based compounds. These compounds can be further explored for their potential applications in various areas, such as materials science, catalysis, and medicinal chemistry.
Used in Material Science:
The compound can also be utilized in material science as a component in the development of new materials with specific properties, such as conductivity, magnetism, or optical activity. The unique structure of 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride allows for the creation of complex molecular architectures that can be tailored for specific applications.

Upstream product

• 1134-35-6 4,4'-dimethyl-2,2'-bipyridines 
• 103946-54-9 4'-methyl-2,2'-bipyridine-4-carboxylic acid 

Downstream Products

• 913341-46-5 bis(4'-methyl-2,2'-bipyridinyl-4-carboxamide)-N,N'-(4,4'-biphenylene) 
• 1393556-22-3 [Zn((C₅H₂N)4(C₆H₅)3)C₆H₄NHC(O)C₆H₃(OCH₃)NHC(O)(C₁₀H₆N₂CH₃)] 
• 1208003-60-4 C₂₈H₂₄N₆ 
• 1065270-60-1 4-methyl-2,2'-bipyridine-4'-carboxyamidyl-4-(tert-butylphenyl) 
• 1065473-88-2 5-(4-(4-methyl-2,2'-bipyridine-4'-carboxyamidyl)phenyl)-10,15,20-triphenylporphyrinatopalladium(II) 
• 244004-92-0 5-[4-(4-methyl-2,2'-bipyridine-4'-carboxyamidyl)phenyl]-10,15,20-triphenylporphyrinatozinc(II) 
• 913341-45-4 bis(4'-methyl-2,2'-bipyridinyl-4-carboxamide)-N,N'-(1,4-phenylene) 
• 133308-60-8 4-methyl-2,2'-bipyridyl-N-(5-p-phenylene-10,15,20-tri-p-tolylporphyrin)-4'-amide 
• 1328942-20-6 4-methyl-2,2'-bipyridine-4'-CONH-3-(2-benzoimidazole)-L-tyrosine ethyl ester 
• 1328942-29-5 4-methyl-2,2'-bipyridine-4'-CONH-3-(pyrid-2'-yl)-L-tyrosine ethyl ester 
• 1328942-25-1 4-methyl-2,2'-bipyridine-4'-CONH-3-(2-methlylenebenzoimidazole)-O-allyl-L-tyrosine ethyl ester 

Relevant articles and documents

Tris(rhenium fac-tricarbonyl) Polypyridine Functionalized Cyclotriguaiacylene Ligands with Rich and Varied Emission

Trinuclear rhenium fac-tricarbonyl bromide complexes have been synthesized coordinated to the host ligands tris(4-[4-methyl-2,2′-bipyridyl]methyl)cyclotriguaiacylene (L1), tris(4-[4-methyl-2,2′-bipyridoyl])cyclotriguaiacylene (L2), and tris(4-[2,2′,6′,2″-terpyridyl]benzyl)cyclotriguaiacylene (L3). The structure of L1 and complexes [{Re(CO)3Br}3(L1)] (1) and [{Re(CO)3Br}3(L3)] (3) have been elucidated through X-ray single-crystal diffraction, with complex 3 crystallizing as a conglomerate. The steady-state luminescent properties and time-resolved fluorescence studies of the complexes have been conducted and revealed an unusual dual-emission phenomenon for complex 2. Complexes 1 and 2 show red-shifted emission wavelengths in comparison with those typical of monometallic Re(CO)3-bipy-Br complexes, while complex 3 showed an unusual excitation-dependent variation of emission wavelength.

Metal-organic approach to binary optical memory

Two new Ru(II) diimine chromophores, each containing a single photochromic dianthryl unit, have been prepared and characterized. The photoluminescence from the Ru(II) complexes is modulated by the photochromic action of the dianthryl species, which serves as a triplet energy transfer quencher in one photochromic state. The coupling of the dianthryl photochromic action to the Ru(II) complex emission permits nondestructive photoluminescence readout of binary information photochemically recorded on the molecular level. Luminescent images stored on polystyrene films that contain these molecules maintained their integrity for periods of months with no apparent degradation or variation in the image resolution, suggesting their durability for long-term storage in read-only memory applications. Copyright

A novel ruthenium(II) tris(bipyridine)-zinc porphyrin-rhenium carbonyl triad: Synthesis and optical properties

A novel ruthenium(II) tris(bipyridine)-zinc porphyrin-rhenium carbonyl triads and its free base porphyrin derivative were synthesized and characterized by 1H, 13C NMR, UV-vis, mass-spectrometry and elemental analysis. The redox poten

Re(I) sensitised near-infrared lanthanide luminescence from a hetero-trinuclear Re2Ln array

The trinuclear complexes Re2Ln (Ln = Nd, Yb or Er) contain two ReI tricarbonyl units linked to a DTPA binding site via 2,2′-bipyridyl ligands; LnIII-centred emission is sensitised by the ReI MLCT excited states.

Bioactive half-sandwich Rh and Ir bipyridyl complexes containing artemisinin

Reaction of dihydroartemisinin (DHA) with 4-methyl-4′-carboxy-2,2′-bipyridine yielded the new ester derivative L1. Six novel organometallic half-sandwich chlorido Rh(III) and Ir(III) complexes (1–6) containing pentamethylcyclopentadienyl, (Cp*), tetramethylphenylcyclopentadienyl (Cpxph), or tetramethylbiphenylcyclopentadienyl (Cpxbiph), and N,N-chelated bipyridyl group of L1, have been synthesized and characterized. The complexes were screened for inhibitory activity against the Plasmodium falciparum 3D7 (sensitive), Dd2 (multi-drug resistant) and NF54 late stage gametocytes (LSGNF54), the parasite strain Trichomonas vaginalis G3, as well as A2780 (human ovarian carcinoma), A549 (human alveolar adenocarcinoma), HCT116 (human colorectal carcinoma), MCF7 (human breast cancer) and PC3 (human prostate cancer) cancer cell lines. They show nanomolar antiplasmodial activity, outperforming chloroquine and artemisinin. Their activities were also comparable to dihydroartemisinin. As anticancer agents, several of the complexes showed high inhibitory effects, with Ir(III) complex 3, containing the tetramethylbiphenylcyclopentadienyl ligand, having similar IC50 values (concentration for 50% of maximum inhibition of cell growth) as the clinical drug cisplatin (1.06–9.23 μM versus 0.24–7.2 μM, respectively). Overall, the iridium complexes (1–3) are more potent compared to the rhodium derivatives (4–6), and complex 3 emerges as the most promising candidate for future studies.

Photoelectrochemical properties of dyads composed of porphyrin/ruthenium catalyst grafted on metal oxide semiconductors

In the current work, we present the use of two free-base and two zinc-metallated porphyrin-ruthenium(II) polypyridine dyads, along with two reference porphyrin derivatives, as sensitizers in both n- and p-type DSSCs and DSPECs. Two of the dyads contain th

A Multi-action and Multi-target RuII–PtIV Conjugate Combining Cancer-Activated Chemotherapy and Photodynamic Therapy to Overcome Drug Resistant Cancers

PtII complexes are commonly used to treat cancer. To reduce their side effects and improve their pharmacological properties, PtIV complexes are being developed as prodrug candidates that are activated by reduction in cancer cells. Concomitantly, RuII polypyridine complexes have gained much attention as photosensitizers for use in photodynamic therapy due to their attractive characteristics. In this article, a novel PtIV–RuII conjugate, which combines cancer activated chemotherapy with PDT, is presented. Upon entering the cancer cell, the PtIV centre is reduced to PtII and the axial ligands including the RuII complex and phenylbutyrate are released. As each component has its individual targets, the conjugate exerts a multi-target and multi-action effect with (photo-)cytotoxicity values upon irradiation up to 595 nm in the low nanomolar range in various (drug resistant) 2D monolayer cancer cells and 3D multicellular tumour spheroids.