912934-77-1

Basic information

• Product Name: 6-bromopyridine-2-sulfonyl chloride
• Synonyms: 6-bromopyridine-2-sulfonyl chloride;2-Pyridinesulfonyl chloride, 6-bromo- 2-Pyridinesulfonyl chloride, 5-bromo- ;2-Pyridinesulfonyl chloride, 6-bromo-;6-Bromo-2-pyridinesulfonyl chloride
• CAS NO: 912934-77-1
• Molecular Formula: C₅H₃BrClNO₂S
• Molecular Weight: 256.50482
• Mol File: 912934-77-1.mol

Chemical Properties

• Boiling Point: 349.3 °C at 760 mmHg
• Flash Point: 165.1 °C
• Appearance: /
• Density: 1.893g/cm³
• Vapor Pressure: 9.55E-05mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 6-bromopyridine-2-sulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromopyridine-2-sulfonyl chloride(912934-77-1)
• EPA Substance Registry System: 6-bromopyridine-2-sulfonyl chloride(912934-77-1)

Safety Data

• Hazardous Substances Data: 912934-77-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-bromopyridine-2-sulfonyl chloride is utilized as a reagent in the preparation of various pharmaceutical compounds. Its versatile reactivity and functional group compatibility make it a crucial building block in the development of novel chemical entities for therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 6-bromopyridine-2-sulfonyl chloride is employed as a reagent for the synthesis of agrochemical compounds. Its unique chemical properties contribute to the development of effective and innovative products for agricultural use.
Used in Organic Synthesis:
6-bromopyridine-2-sulfonyl chloride is used as a key intermediate in the synthesis of complex organic molecules. Its unique sulfonyl chloride group allows for various chemical reactions, facilitating the creation of diverse organic compounds for research and industrial applications.
Used in Medicinal Chemistry:
As a valuable building block in medicinal chemistry, 6-bromopyridine-2-sulfonyl chloride is employed in the design and synthesis of new pharmaceutical agents. Its functional group compatibility and reactivity enable the development of novel chemical entities with potential therapeutic benefits.

InChI:InChI=1/C5H3BrClNO2S/c6-4-2-1-3-5(8-4)11(7,9)10/h1-3H

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 93681-52-8 2-benzylsulphenyl-6-bromopyridine 

Downstream Products

• 856013-04-2 6-bromopyridine-2-sulfonamide 
• 1043446-39-4 C⁽³⁷²⁾H₅₁₉₁ 
• 1259327-74-6 6-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]pyridine-2-sulfonic acid amide 
• 1043446-52-1 C₂₇H₂₇N₃O₃S 
• 1043446-58-7 6-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]pyridine-2-sulfonic acid dibenzylamide 
• 1259327-72-4 6-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]pyridine-2-sulfonic acid dibenzylamide 
• 1043446-54-3 2-(6-dibenzylsulfamoylpyridin-2-ylamino)-2-methylpropionic acid methyl ester 
• 1043446-53-2 6-aminopyridine-2-sulfonic acid dibenzylamide 
• 1043446-50-9 6-bromopyridine-2-sulfonic acid dibenzylamide 
• 874959-45-2 phenyl 6-bromo-2-pyridinesulfonate 

Relevant articles and documents

Selective IKur Inhibitors for the Potential Treatment of Atrial Fibrillation: Optimization of the Phenyl Quinazoline Series Leading to Clinical Candidate 5-[5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide

We have recently disclosed 5-phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine 1 as a potent IKur current blocker with selectivity versus hERG, Na and Ca channels, and an acceptable preclinical PK profile. Upon further characterization in vivo, compound 1 demonstrated an unacceptable level of brain penetration. In an effort to reduce the level of brain penetration while maintaining the overall profile, SAR was developed at the C2′ position for a series of close analogues by employing hydrogen bond donors. As a result, 5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide (25) was identified as the lead compound in this series. Compound 25 showed robust effects in rabbit and canine pharmacodynamic models and an acceptable cross-species pharmacokinetic profile and was advanced as the clinical candidate. Further optimization of 25 to mitigate pH-dependent absorption resulted in identification of the corresponding phosphoramide prodrug (29) with an improved solubility and pharmacokinetic profile.

Efficient and scalable synthesis of pyridine sulfonamides

Short-step and scalable transformations from 2,6-dibromopyridine to 6-bromopyridine-2-sulfonamide by means of halogen-metal exchange and subsequent reaction with sulfuryl chloride followed by amidation are established. Application of the method for the synthesis of various pyridine sulfonamides is also described. Georg Thieme Verlag Stuttgart - New York.

Design and synthesis of an androgen receptor pure antagonist (CH5137291) for the treatment of castration-resistant prostate cancer

A series of 5,5-dimethylthiohydantoin derivatives were synthesized and evaluated for androgen receptor pure antagonistic activities for the treatment of castration-resistant prostate cancer. Since CH4933468, which we reported previously, had a problem wit

PIPERAZINE DERIVATIVES USEFUL FOR THE TREATMENT OF GASTROINTESTINAL DISORDERS

The invention provides compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein Ra, Rb, Rc, Rd, Re, Rf and Y are as defined in the specification. The compounds are partial or full agonists at the growth hormone secretagogue (GHS) receptors . Pharmaceutical compositions comprising the compounds, methods of preparing the compounds, uses of the compounds and methods involving the compounds are also provided.

Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides

A series of arene and heteroarene sulfonamides were prepared in one vessel from aryl and heteroaryl bromides via conversion into the corresponding Grignard reagents using either magnesium or isopropylmagnesium chloride and subsequent reaction with sulfur dioxide, sulfuryl chloride, and an amine.