162607-23-0

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dimethylthiophene-3-boronic acid is used as a key intermediate in the synthesis of KRAS G12C inhibitors for the treatment of various cancers. These inhibitors target the KRAS protein, which is a common mutation found in pancreatic, colorectal, and lung cancers. By inhibiting the KRAS protein, these drugs can potentially slow down or stop the growth of cancer cells, offering a promising therapeutic approach for patients with these types of cancers.

InChI:InChI=1/C6H9BO2S/c1-4-3-6(7(8)9)5(2)10-4/h3,8-9H,1-2H3

Upstream product

• 31819-37-1 3-bromo-2,5-dimethylthiophene 
• 638-02-8 2,5-DIMETHYLTHIOPHENE 
• 39129-54-9 3,4-dibromo-2,5-dimethylthiophene 
• 688-74-4 boric acid tributyl ester 
• 5419-55-6 Triisopropyl borate 
• 154566-69-5 3-bromo-2-methylthiophene-5-boronic acid 
• 554-14-3 2-Methylthiophene 
• 29421-73-6 3,5-dibromo-2-methylthiophene 
• 40197-02-2 3-iodo-2,5-dimethylthiophene 
• 122-56-5 tributyl borane 
• 1310-73-2 sodium hydroxide 

Downstream Products

• 928765-78-0 1-(4-methoxyphenyl)-4,5-bis-(2,5-dimethyl-3-thienyl)-2-(2'-pyridyl)imidazole 
• 928765-81-5 1-(4-methylphenyl)-4,5-bis-(2,5-dimethyl-3-thienyl)-2-(2'-pyridyl)imidazole 
• 1198357-61-7 2,3,5,6-tetrakis(2,5-dimethylthien-3-yl)-4-phenyldithieno[3,2-b:2',3'-d]pyrrole 
• 1198357-62-8 2,3,5,6-tetrakis(2,5-dimethylthien-3-yl)-4-(p-tolyl)dithieno[3,2-b:2',3'-d]pyrrole 
• 1198357-63-9 4-(p-methoxyphenyl)-2,3,5,6-tetrakis(2,5-dimethylthien-3-yl)dithieno[3,2-b:2',3'-d]pyrrole 
• 1198357-64-0 4-(p-chlorophenyl)-2,3,5,6-tetrakis(2,5-dimethylthien-3-yl)dithieno[3,2-b:2',3'-d]pyrrole 
• 1263049-56-4 C₂₀H₁₆N₂S₂ 
• 1263049-59-7 C₂₀H₁₄N₂O₂S 
• 1263049-54-2 C₂₀H₁₇NO₂S₂ 
• 147699-65-8 4,5-bis-(4-hydroxyphenoxy)phthalonitrile 
• 1263049-57-5 C₁₆H₁₅BrO₄S 
• 1263049-51-9 C₂₂H₂₂O₄S₂ 
• 1364740-75-9 C₃₈H₂₇BF₃NS₃ 
• 1364740-81-7 C₄₀H₂₅BF₉NS₃ 

Relevant academic research and scientific papers

Synthesis of 3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione from mucobromic acid

Palladium-catalyzed cross-coupling between 2,5-dimethyl-3-thienylboronic and mucobromic acids under phase transfer catalysis (PTC) conditions gave the expected 3,4-bis(2,5-dimethyl-3-thienyl)-5-hydroxyfuran-2-one in 32% yield. The by-product was 2,2',5,5'

Triplet MLCT photosensitization of the ring-closing reaction of diarylethenes by design and synthesis of a photochromic rhenium(I) complex of a diarylethene-containing 1,10-phenanthroline ligand

Synthesis of the diaryle-thene-containing ligand LI based on Suzuki cross-coupling reaction between thienyl boronic acid and the dibromophenanthroline ligand is reported. On coordination to the rhenium(I) tricarbonyl complex system, the photochromism of L1 could be photosensitized and consequently extended from intraligand excitation at λ≤340nm in the free ligand to metal-to-ligand charge-transfer (MLCT) excitation atλ≤480nm in the complex. The photo-chromic reactions were studied by 1HNMR, UV/Vis, and steady-state emission spectroscopy. Photosensitization was further probed by ultrafast transient absorption and time-resolved emission spectroscopy. The results provided direct evidence that the formation of the closed form by the MLCT-sensitized photochromic process was derived from the 3MLCT excited state. This supports the photosensitization mechanism, which involves an intramolecular energy-transfer process from the 3MLCT to the 3IL(L1) state that initiated the ring-closure reaction. The photophysical and electrochemical properties of the complex were also investigated.

The Photostability of Two Optical Materials Based on Perylene Diimide Substituted by Different Aromatic Groups at the Bay Area

The perylene diimide substituented by thiophene rings at bay area shows photoactivity and can be used as a photo sensor, but another one substituented by mestylene groups is photostable. The single crystal of 1,7-mesitylene perylene diimide was obtained. X-ray diffraction data of the crystal revealed that the plane of the perylene core was hardly twisted by introduction of mesitylene groups. These mestylene groups are like clips maintaining the planarity of the perylene core. Density functional theory calculation was applied to study the difference of photophysical and photochemical properties. The discovery is valuable for design guidance of perylene diimides.

Synthesis, Characterization, and Properties of Iron(II) Spin-Crossover Molecular Photoswitches Functioning at Room Temperature

Spin-crossover molecular switches [FeII(H2B(pz)2)2L] (L = novel phenanthroline-based ligands featuring photochromic diarylethene units; pz = 1-pyrazolyl) were synthesized and thoroughly characterized by variable

The mechanodonor-acceptor coupling (MDAC) approach for unidirectional multi-state fluorochromism

Uni-directional multi-state fluorochromic scaffolds are valuable photofunctional molecules and yet scarce. We report a general approach for their design, i.e., mechanodonor-acceptor coupling (MDAC). A photochromic molecule is a mechanodonor, due to its capability to convert photonic energy into mechanical force. Upon proper coupling, it can be used to drive a mechanochromic molecule for uni-directional multi-state fluorochromism. The embodiment of this approach is a rhodamine-dithienylethylene hydride (RDH), which has been successfully employed in super-resolution localization microscopy[Figure not available: see fulltext.]

Development of High-Performance Pyrimidine Nucleoside and Oligonucleotide Diarylethene Photoswitches

Nucleosidic and oligonucleotidic diarylethenes (DAEs) are an emerging class of photochromes with high application potential. However, their further development is hampered by the poor understanding of how the chemical structure modulates the photochromic properties. Here we synthesized 26 systematically varied deoxyuridine- and deoxycytidine-derived DAEs and analyzed reaction quantum yields, composition of the photostationary states, thermal and photochemical stability, and reversibility. This analysis identified two high-performance photoswitches with near-quantitative, fully reversible back-and-forth switching and no detectable thermal or photochemical deterioration. When incorporated into an oligonucleotide with the sequence of a promotor, the nucleotides maintained their photochromism and allowed the modulation of the transcription activity of T7 RNA polymerase with an up to 2.4-fold turn-off factor, demonstrating the potential for optochemical control of biological processes.

Photoinduced Changes in Aromaticity Facilitate Electrocyclization of Dithienylbenzene Switches

The concepts of excited-state aromaticity and antiaromaticity have in recent years with increasing frequency been invoked to rationalize the photochemistry of cyclic conjugated organic compounds, with the long-term goal of using these concepts to improve

The role of alkyl substituents in deazaadenine-based diarylethene photoswitches

Diarylethenes are an important class of reversible photoswitches and often claimed to require two alkyl substituents at the carbon atoms between which the bond is formed or broken in the electrocyclic rearrangement. Here we probe this claim by the synthesis and characterization of four pairs of deazaadenine-based diarylethene photoswitches with either one or two methyl groups at these positions. Depending on the substitution pattern, diarylethenes with one alkyl group can exhibit significant photochromism, but they generally show poor stability towards extended UV irradiation, low thermal stability, and decreased fatigue resistance. The results obtained provide an important direction for the design of new efficient DNA photoswitches for the application in bionanotechnology and synthetic biology.

A dithienylethene-based rewritable hydrogelator

Dithienylethene photochromic switching units have been incorporated into a hydrogelating system based on a tripeptide motif. The resulting hybrid system provided both a photochromic response and the ability to gelate water under acidic and neutral conditi

Substituent and solvent effects on the fluorescent and photochromic properties of 2-(2-pyridyl)imidazole containing diarylethene derivatives

Five diarylethene derivatives with 2-(2-pyridyl)imidazole as the ethene bridges (PI-BTEs) were synthesized and characterized. The structures and performances of the PI-BTEs (L1-L5) could be modified from not only the thiophene unit, but also the substituent on the imidazole nitrogen. Noteworthily, replacing the thiophene with the benzothiophene, the fatigue resistance is significantly improved, the centre absorption bands of the closed forms shift from 572 nm (L3) to 550 nm (L2), and the colours of the solutions change from pale pink in L3 to red-purple in L2. Additionally, the Stokes shift (Δν) values of L3 in various solvents display good linear relationships with the donor number (DN) of the solvents, and the solvent polarity parameter Δf.