458532-96-2

Basic information

• Product Name: 2-Chloro-4-pyridylboronic acid
• Synonyms: AKOS BRN-0495;2-CHLORO-4-PYRIDINEBORONIC ACID;2-CHLORO-4-PYRIDINYLBORONIC ACID;2-CHLORO-4-PYRIDYLBORONIC ACID;2-CHLOROPYRIDINE-4-BORONIC ACID;2-CHLOROPYRIDIN-4-YLBORONIC ACID;Boronic acid, (2-chloro-4-pyridinyl)- (9CI);2-Chloropyridine-4-Boronic
• CAS NO: 458532-96-2
• Molecular Formula: C₅H₅BClNO₂
• Molecular Weight: 157.36
• EINECS: 1533716-785-6
• Product Categories: BORONICACID;blocks;BoronicAcids;Pyridines;Boronic acids;Boronic acid;Organoborons;Pyridine;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;Boric acid series;Boronate Ester;Potassium Trifluoroborate
• Mol File: 458532-96-2.mol

Chemical Properties

• Melting Point: 155-163 °C
• Boiling Point: 355.186 °C at 760 mmHg
• Flash Point: 168.611 °C
• Appearance: /
• Density: 1.41 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: 2-8°C
• PKA: 6.57±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-4-pyridylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-pyridylboronic acid(458532-96-2)
• EPA Substance Registry System: 2-Chloro-4-pyridylboronic acid(458532-96-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 458532-96-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
2-Chloro-4-pyridylboronic acid is used as a substrate in peroxide-mediated hydroxydeboronation reactions, which provide good yields of halohydroxypyridines. These halohydroxypyridines are important intermediates in the synthesis of various pharmaceutical compounds and have potential applications in the development of new drugs.
Used in Pharmaceutical Industry:
2-Chloro-4-pyridylboronic acid is used as a reagent for the preparation of IRAK-4 inhibitors. IRAK-4 (interleukin-1 receptor-associated kinase 4) is a key enzyme involved in the regulation of inflammatory responses and plays a crucial role in the activation of the immune system. Inhibitors of IRAK-4 have potential therapeutic applications in the treatment of various inflammatory diseases, such as rheumatoid arthritis, inflammatory bowel disease, and asthma.

InChI:InChI=1/C5H5BClNO2/c7-5-3-4(6(9)10)1-2-8-5/h1-3,9-10H

Upstream product

• 73583-37-6 2-chloro-4-bromopyridine 
• 121-43-7 Trimethyl borate 

Downstream Products

• 643082-10-4 2,2'-dichloro-3,4'-bipyridine 
• 958657-25-5 1-[3-(2-Chloro-pyridin-4-yl)-phenyl]-ethanone 
• 1248589-28-7 2-chloro-4-(4-phenyl-1H-pyrazol-1-yl)pyridine 
• 1107655-24-2 3-[2-amino-3-(2-chloro-pyridin-4-yl)imidazo[1,2-b]pyridazin-7-yl]-N-methyl-benzamide 
• 1107655-21-9 3-[3-(2-Chloro-pyridin-4-yl)-imidazo[1,2-b]pyridazin-7-yl]-N-methyl-benzamide 
• 1123158-01-9 4-[3-{6-[3-(2-chloro-pyridin-4-yl)-5-thiophen-3-yl-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester 
• 1095708-30-7 tert-Butyl 4-[3-(2-chloropyrid-4-yl)-2-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]piperazine-1-carboxylate 
• 1202366-51-5 methyl 4-(2-chloropyridin-4-yl)-2-methoxybenzoate 
• 1202366-52-6 methyl 5-(2-chloropyridin-4-yl)-2-methoxybenzoate 
• 1161361-91-6 2-chloro-4-(2-methoxy-4-nitrophenyl)pyridine 
• 942190-06-9 C₃₁H₂₁ClN₄O₂ 
• 923597-85-7 4-[3-(2-chloro-pyridin-4-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol 
• 929040-24-4 methyl 5-[5-(2-chloropyridin-4-yl)-1H-benzimidazol-1-yl]-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)thiophene-2-carboxylate 
• 866545-95-1 3-(2-chloropyridin-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

Flow Chemistry on Multigram Scale: Continuous Synthesis of Boronic Acids within 1 s

The benefits and limitations of a simple continuous flow setup for handling and performing of organolithium chemistry on the multigram scale is described. The developed metalation platform embodies a valuable complement to existing methodologies, as it combines the benefits of Flash Chemistry (chemical synthesis on a time scale of 1 s) with remarkable throughput (g/min) while mitigating the risk of blockages.

Synthesis of novel halopyridinylboronic acids and esters. Part 3: 2, or 3-Halopyridin-4-yl-boronic acids and esters

This paper describes a general method for the synthesis and the isolation of novel 2, or 3-halopyridin-4-yl-boronic acids and esters 12-14, 18-20. These compounds are prepared taking in account a regioselective halogen-metal exchange using nBuLi or direct