Sodium pyridine-2-sulfinate

  • CAT Number: R073942
  • CAS Number: 24367-66-6
  • PubChem Substance ID: 23678794
  • Molecular Formula: C5H4NNaO2S
  • Molecular Weight: 165.142
  • Purity: ≥95%
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Catalog Number R073942
CAS Number 24367-66-6
Molecular Formula

C5H4NNaO2S

Purity 95%
IUPAC Name sodium;pyridine-2-sulfinate
InChI InChI=1S/C5H5NO2S.Na/c7-9(8)5-3-1-2-4-6-5;/h1-4H,(H,7,8);/q;+1/p-1
InChIKey HQCGASCBCQJRDJ-UHFFFAOYSA-M
SMILES C1=CC=NC(=C1)S(=O)[O-].[Na+]
Reference

[1]. Mungalpara, M.N., Plieger, P.G. and Rowlands, G.J., 2021.<br />
The Synthesis of Pyridyl [2.2] paracyclophanes by Palladium‐Catalyzed Cross‐Coupling of Pyridine Sulfinates.<br />
Abstract: Substituted planar chiral pyridyl[2.2]paracyclophanes were prepared by the palladium-catalyzed desulfinative cross-coupling of bromo[2.2]paracyclophanes and pyridine sulfinate salts. Pyridine-substituted [2.2]paracyclophanes are useful building blocks in the preparation of catalysts, functionalized materials, and luminescent molecules. Yet the synthesis of many pyridine-substituted [2.2]paracyclophanes is more challenging than expected due to the instability of traditional coupling partners. Pyridine sulfinates offer a solution to this shortcoming, permitting pyridyl[2.2]paracyclophanes to be prepared from readily available bromo[2.2]paracyclophanes. Our preliminary results indicate the potential of this chemistry. Amine, bromine and ester substituted planar chiral pyridines that are hard to synthesize by other methods were formed but formation of (bis)pyridines is still problematic.<br />
Advanced Synthesis &amp; Catalysis, 363(4), pp.1069-1080.<br />
<br />
[2]. Liang, S. and Manolikakes, G., 2016.<br />
Copper‐Catalyzed Remote C&minus; H Functionalization of 8‐Aminoquinolines with Sodium and Lithium Sulfinates.<br />
Abstract: A simple and mild copper-catalyzed sulfonylation of 8-aminoquinolines with sodium and lithium sulfinates is reported. In the presence of manganese(III) acetate [Mn(OAc)3] as cooxidant a highly site-selective C&minus;H functionalization at the C-5 position takes place. The reaction proceeds readily at room temperature in air and various sulfones were synthesized in moderate to high yields. Moreover, a straightforward procedure for the conversion of organolithium reagents and sulfur dioxide into C-5 sulfonylated quinolines was developed.<br />
Advanced Synthesis &amp; Catalysis, 358(15), pp.2371-2378.<br />
<br />
[3]. Chen, Z., Bolat, H., Wan, X. and Li, Y., 2014.<br />
Crystal structure of 2-[(dichloromethane) sulfonyl] pyridine.<br />
Abstract: The asymmetric unit of the title compound, C6H5Cl2NO2S, contains two mol&shy;ecules with similar conformations (r.m.s. overlay fit for the non-H atoms = 0.067 &Aring;). Atoms attached to the pendent Csp3-S bond are arranged in a staggered conformation with one of the Cl atoms anti to the C atom in the aromatic ring [C-S-C-Cl torsion angles = 178.41 (11) and -176.70 (13)&deg;]. In the crystal, mol&shy;ecules are linked by C-H…N and C-H…O hydrogen bonds, generating a three-dimensional network, and weak aromatic [pi]-[pi] stacking is also observed [centroid-centroid separation = 3.8902 (17) &Aring;].<br />
Acta Crystallographica Section E: Structure Reports Online, 70(12), pp.o1272-o1272.<br />
<br />
[4]. Sain, S., Jain, S., Srivastava, M., Vishwakarma, R. and Dwivedi, J., 2019.<br />
Application of palladium-catalyzed cross-coupling reactions in organic synthesis.<br />
Abstract: Palladium-catalyzed cross-coupling reactions have gained a continuously growing interest of synthetic organic chemists. The present review gives a brief account of applications of the palladium-catalyzed cross-coupling reactions in comprehensive synthesis, viz., the Heck, Stille, Suzuki&ndash;Miyaura, Negishi, Sonogashira, Buchwald&ndash;Hartwig, Ullmann and the Oxidative, decarboxylative cross-coupling reactions, with particular emphasis on the synthesis of heterocyclic compounds.<br />
Current organic synthesis, 16(8), pp.1105-1142.<br />
<br />
[5]. Aiyao, L., Jiang, L., Haibo, M., R&ouml;schenthaler, G.V. and Jianlin, H., 2020.<br />
Selectfluor-Promoted Twofold Sulfination of Alcohols for the Synthesis of Sulfinic Ester from Diaryldisulfides.<br />
Chinese Journal of Organic Chemistry, 40(7), pp.1926-1933.

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