847664-64-6

Basic information

• Product Name: 2,5-DICHLOROPYRIDINE-4-BORONIC ACID
• Synonyms: 2,5-DICHLORO-4-PYRIDINEBORONIC ACID;2,5-DICHLOROPYRIDIN-4-YLBORONIC ACID;2,5-DICHLOROPYRIDINE-4-BORONIC ACID;Boronic acid, B-(2,5-dichloro-4-pyridinyl)-;B-(2,5-Dichloro-pyridin-4-yl)boronic acid;2,5-Dichloropyridine-4-boronic Acid (contains varying amounts of Anhydride)
• CAS NO: 847664-64-6
• Molecular Formula: C5H4BCl2NO2
• Molecular Weight: 191.81
• Product Categories: Pyridine
• Mol File: 847664-64-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 150°C
• Boiling Point: 368.9 °C at 760 mmHg
• Flash Point: 176.9 °C
• Appearance: White to cream-colored crystalline powder
• Density: 1.56
• Vapor Pressure: 4.29E-06mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 6.27±0.58(Predicted)
• CAS DataBase Reference: 2,5-DICHLOROPYRIDINE-4-BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DICHLOROPYRIDINE-4-BORONIC ACID(847664-64-6)
• EPA Substance Registry System: 2,5-DICHLOROPYRIDINE-4-BORONIC ACID(847664-64-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 847664-64-6(Hazardous Substances Data)

Usage

General Description

2,5-Dichloropyridine-4-boronic acid is a chemical compound used primarily in organic synthesis and medicinal chemistry. It is a boronic acid derivative of 2,5-dichloropyridine, which has two chlorine atoms attached to the pyridine ring. 2,5-DICHLOROPYRIDINE-4-BORONIC ACID is a valuable building block in the formation of heterocyclic compounds and is commonly used in the development of pharmaceuticals, agrochemicals, and materials science. As a boronic acid, it has the ability to form reversible covalent bonds with various substrates, making it a versatile reagent in organic reactions such as Suzuki cross-coupling reactions, cycloadditions, and carbon-carbon bond formations. Its unique chemical properties make it an important tool in the synthesis of complex molecules and drug discovery research.

InChI:InChI=1/C5H4BCl2NO2/c7-4-2-9-5(8)1-3(4)6(10)11/h1-2,10-11H

Upstream product

• 16110-09-1 2,5 dichloropyridine 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 1608503-32-7 7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide 
• 1608503-33-8 7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-(2-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide 
• 1608503-34-9 C₂₅H₂₂ClFN₆O 
• 1608503-35-0 7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide 
• 1608503-36-1 C₂₅H₂₁ClF₂N₆O 
• 1608503-42-9 phenyl 7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate 

Relevant articles and documents

Design, Synthesis, and Structure-Activity Relationship of Tetrahydropyrido[4,3-d]pyrimidine Derivatives as Potent Smoothened Antagonists with in Vivo Activity

Medulloblastoma is one of the most prevalent brain tumors in children. Aberrant hedgehog (Hh) pathway signaling is thought to be involved in the initiation and development of medulloblastoma. Vismodegib, the first FDA-approved cancer therapy based on inhibition of aberrant hedgehog signaling, targets smoothened (Smo), a G-protein coupled receptor (GPCR) central to the Hh pathway. Although vismodegib exhibits promising therapeutic efficacy in tumor treatment, concerns have been raised from its nonlinear pharmacokinetic (PK) profiles at high doses partly due to low aqueous solubility. Many patients experience adverse events such as muscle spasms and weight loss. In addition, drug resistance often arises among tumor cells during treatment with vismodegib. There is clearly an urgent need to explore novel Smo antagonists with improved potency and efficacy. Through a scaffold hopping strategy, we have identified a series of novel tetrahydropyrido[4,3-d]pyrimidine derivatives, which exhibited effective inhibition of Hh signaling. Among them, compound 24 is three times more potent than vismodegib in the NIH3T3-GRE-Luc reporter gene assay. Compound 24 has a lower melting point and much greater solubility compared with vismodegib, resulting in linear PK profiles when dosed orally at 10, 30, and 100 mg/kg in rats. Furthermore, compound 24 showed excellent PK profiles with a 72% oral bioavailability in beagle dogs. Compound 24 demonstrated overall favorable in vitro safety profiles with respect to CYP isoform and hERG inhibition. Finally, compound 24 led to significant regression of subcutaneous tumor generated by primary Ptch1-deficient medulloblastoma cells in SCID mouse. In conclusion, tetrahydropyrido[4,3-d]pyrimidine derivatives represent a novel set of Smo inhibitors that could potentially be utilized to treat medulloblastoma and other Hh pathway related malignancies.