Pyridine-2-sulfonyl fluoride

Base Information

• Chemical Name: Pyridine-2-sulfonyl fluoride
• CAS No.: 878376-35-3
• Molecular Formula: C₅H₄FNO₂S
• Molecular Weight: 161.157
• Hs Code.: 2933399990
• European Community (EC) Number: 819-734-5
• DSSTox Substance ID: DTXSID90469460
• Nikkaji Number: J2.289.066B
• Wikidata: Q82297191
• Mol file: 878376-35-3.mol

Synonyms:Pyridine-2-sulfonyl fluoride;878376-35-3;2-Pyridinesulfonyl fluoride;PyFluor;2-Pyridinesulfonylfluoride;Pyridine-2-sulfonylfluoride;Pyridine-2-sulphonyl fluoride;C5H4FNO2S;SCHEMBL18606310;DTXSID90469460;AMY16251;MFCD09265513;AKOS015854379;DS-11797;CS-0105322;P2398;EN300-244367;A862392;Z1255446838

Chemical Property of Pyridine-2-sulfonyl fluoride

Chemical Property:

• Vapor Pressure: 0.079mmHg at 25°C
• Melting Point: 29-34°C
• Refractive Index: 1.502
• Boiling Point: 234.939°C at 760 mmHg
• PKA: -3.93±0.19(Predicted)
• Flash Point: 95.888°C
• PSA: 55.41000
• Density: 1.421g/cm³
• LogP: 1.82060
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 160.99467771
• Heavy Atom Count: 10
• Complexity: 196

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-PyridinesulfonylFluoride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)S(=O)(=O)F
• Uses: Novel thermally stable deoxyfluorination reagent with a broad substrate scope of alcohols. 2-pyridinesulfonyl fluoride can be used for the deoxyfluorination of primary and secondary alcohols in combination with an amidine or guanidine base. In comparison with other common deoxyfluorination reagents, for example, DAST exhibits less elimination side products in direct comparison on certain substrates.

Technology Process of Pyridine-2-sulfonyl fluoride

There total 3 articles about Pyridine-2-sulfonyl fluoride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

2-Sulfanylpyridine (2637-34-5,73018-10-7) → pyridine-2-sulfonyl fluoride (878376-35-3)

Guidance literature:

With pyridine; hydrogenchloride; potassium fluoride; water; In acetonitrile; at 20 ℃; for 6h; Electrochemical reaction; Green chemistry;

DOI:10.1021/jacs.9b06126

Reference yield:

2-(pyridin-2-ylthio)isoindoline-1,3-dione → pyridine-2-sulfonyl fluoride (878376-35-3)

Guidance literature:

With methanol; potassium fluoride; trichloroisocyanuric acid; In acetonitrile; at 25 ℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;

DOI:10.1002/anie.202009699

Reference yield:

pyridine-2-sulfonyl chloride (66715-65-9) → pyridine-2-sulfonyl fluoride (878376-35-3)

Guidance literature:

With potassium hydrogen difluoride; In water; acetonitrile; at 20 ℃; for 0.333333h;

DOI:10.1021/jacs.5b06307

upstream raw materials:

2-Sulfanylpyridine

pyridine-2-sulfonyl chloride

Downstream raw materials:

4-(2-pyridinyl)anisole

Refernces

• 1、 Laudadio, Gabriele,Bartolomeu, Aloisio De A.,Verwijlen, Lucas M. H. M.,Cao, Yiran,De Oliveira, Kleber T.,No?l, Timothy. "Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride". supporting information. p. 11832 - 11836. Retrieved 2019/08/26.
• 2、 Wright, Stephen W.,Hallstrom, Kelly N.. "A convenient preparation of heteroaryl sulfonamides and sulfonyl fluorides from heteroaryl thiols". . p. 1080 - 1084. Retrieved 2007/10/03.