20277-69-4

Basic information

• Product Name: Sodium methanesulphinate
• Synonyms: Sodium methanesulfinate,Methanesulfinic acid sodium salt;Sodium methanesulphinate, tech;Methanesulfinic acid,sodiuM salt (1:1);Sodium methanesulphinate Methanesulfinic acid sodium salt;Sodium methanesulfinate technical grade, 85%;Sodium methylsulfinate;METHANESULPHINIC ACID SODIUM SALT;METHANESULFINIC ACID
• CAS NO: 20277-69-4
• Molecular Formula: CH₃O₂S*Na
• Molecular Weight: 102.09
• EINECS: 243-669-6
• Product Categories: Aliphatics
• Mol File: 20277-69-4.mol

Chemical Properties

• Melting Point: 222-226 °C (dec.)(lit.)
• Boiling Point: 256.4 °C at 760 mmHg
• Flash Point: 108.9 °C
• Appearance: White to light beige/Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Methanol, Water (Slightly)
• Water Solubility: soluble
• Sensitive: Air Sensitive & Hygroscopic
• Stability: Hygroscopic
• BRN: 3565430
• CAS DataBase Reference: Sodium methanesulphinate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium methanesulphinate(20277-69-4)
• EPA Substance Registry System: Sodium methanesulphinate(20277-69-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-20/21/22
• Safety Statements: 36/37-24/25
• RIDADR: 2811
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 20277-69-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Sodium methanesulfinate is used as a key intermediate in the synthesis of cyclooxygenase-2 inhibitors, which are important for the development of anti-inflammatory and analgesic medications.
Used in Chemical Synthesis:
In the chemical synthesis industry, sodium methanesulfinate serves as a reactant for the preparation of alkyl methyl sulfone, a compound with various applications in organic chemistry.
Used in Synthesis of RAFT Agents:
Sodium methanesulfinate is used as a precursor in the synthesis of sulfonyl type reversible addition-fragmentation transfer (RAFT) agents, benzyl methylsulfonyldithioformate and benzyl phenylsulfonyldithioformate. These RAFT agents are valuable tools in controlled radical polymerization, enabling the production of polymers with specific molecular weights and architectures.
Used in Organic Chemistry:
The conjugate addition of sodium methanesulfinate to vinyl heterocycles and its cross-coupling reaction with aryl boronic acid make it a useful reagent in organic chemistry for the formation of new chemical entities and the modification of existing molecules.

InChI:InChI=1/CH4O2S.Na/c1-4(2)3;/h1H3,(H,2,3);/q;+1/p-1/rCH3NaO2S/c1-5(3)4-2/h1H3

Upstream product

• 77-79-2 3-Sulfolene 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 1192-16-1 2,3-dihydrothiophene-1,1-dioxide 
• 7144-49-2 2-methanesulfonylbenzothiazole 
• 124-63-0 methanesulfonyl chloride 
• 96088-55-0 N,N-bis(methylsulfonyl)hydroxylamine 
• 50-00-0 formaldehyd 
• 676-85-7 methylsulphinyl chloride 
• 42790-82-9 methanesulphonyl iodide 

Downstream Products

• 1027357-11-4 methyl-(4-nitro-phenethyl)-sulfone 
• 835-57-4 methyl 2,4-dinitrophenyl sulfone 
• 56075-39-9 1-(methylsulfonyl)-2-(4-nitrophenyl)diazene 
• 61081-34-3 methyl 4-nitrobenzylsulfone 
• 3112-90-1 benzyl-methyl sulfone 
• 1977-37-3 (methylsulfonyl)propane 
• 2274-42-2 methanesulfonyl-acetonitrile 
• 3708-04-1 2-methylsulfonyl-1-phenylethanone 
• 261924-46-3 1-(methylsulfonylmethyl)-3-nitrobenzene 
• 66913-97-1 2-(methylsulfonyl)acetamide 
• 53271-53-7 S-Methyl-S'-phenyl-trithiocarbonat-S,S-dioxid 
• 104694-53-3 1-Methylsulfonyl-4,4-bis-<4-N,N-dimethylamino-phenyl>-1,2-dicyan-butadien-(1,3) 
• 39213-24-6 Methoxymethyl-methyl-sulfon 
• 103534-91-4 1-Methylsulfonyl-4,4-bis-<4-diethylamino-phenyl>-1,2-dicyan-butadien-(1,3) 

Relevant articles and documents

Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis

N-Heterocyclic carbene (NHC) catalysis has emerged as a versatile tool in modern synthetic chemistry. Further increasing the complexity, several processes have been introduced that proceed via dual catalysis, where the NHC organocatalyst operates in concert with a second catalytic moiety, significantly enlarging the reaction scope. In biological transformations, multiple catalysis is generally used to access complex natural products. Guided by that strategy, triple catalysis has been studied recently, where three different catalytic modes are merged in a single process. In this Communication, direct α-C-H acylation of various alkenes with aroyl fluorides using NHC, sulfinate, and photoredox cooperative triple catalysis is reported. The method allows the preparation of α-substituted vinyl ketones in moderate to high yields with excellent functional group tolerance. Mechanistic studies reveal that these cascades proceed through a sequential radical addition/coupling/elimination process. In contrast to known triple catalysis processes that operate via two sets of interwoven catalysis cycles, in the introduced process, all three cycles are interwoven.

Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol

Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.

Preparation method of substituted sulfinate

The invention discloses a preparation method of substituted sulfinate, which comprises the following steps: by using substituted sulfonyl chloride as a raw material, carrying out hydrolysis reductionreaction on the substituted sulfonyl chloride in water in the presence of a reducing agent and an acid-binding agent to generate the corresponding substituted sulfinate. The method is a novel method which is easy to implement and suitable for industrial scale production and is used for preparing sulfinate and derivatives thereof. The method is simple in technological process, high in product purity and safe and environment-friendly, wherein the waste gas, solid and liquid are easy to treat.

Synthesis of β-ketosulfone derivatives as new non-cytotoxic urease inhibitors in vitro

Background: Peptic ulcer and urolithiasis are largely due to infection caused by urease-producing bacteria. Therefore, the discovery of urease inhibitors is an important area of medicinal chemistry research. Objective: The main aim of the work was to identify novel urease inhibitors with no cytotoxicity. Method: During the current study, a series of β-ketosulfones 1-26 was synthesized in two steps and evaluated for their in vitro urease inhibition potential. Results: Out of twenty-six compounds, seventeen have shown good to significant urease inhibitory activity with IC50 values ranging between 49.93-351.46 μM, in comparison to standard thiourea (IC50 = 21 ± 0.11 μM). Moreover, all compounds found to be non-cytotoxic against normal 3T3 cell line. Conclusion: This study has identified β-ketosulfones as novel and non-cytotoxic urease inhibitors.

Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives

A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.

Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position

An efficient and convenient protocol for the direct sulfonylation of BODIPY dyes with sodium sulfinates via a radical process is described for the first time. This transformation presented wide substrate scope and high regioselectivity, providing a series of α-sulfonylated BODIPYs. Meaningfully, the sulfonyl group, as a good leaving group, allowed the facile introduction of a variety of functionalities on the BODIPY core. Moreover, a 2,4-dinitrobenzenesulfonyl (DBS) group substituted BODIPY showed dramatically quenched fluorescence via the photoinduced electron transfer (PET) pathway, and was demonstrated as a new fluorescent probe for selective biothiol detection. This journal is

Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants

Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.

A Convenient Synthesis of Sulfones via Light Promoted Coupling of Sodium Sulfinates and Aryl Halides

A convenient and e?cient synthesis of sulfones from sulfinates and aryl halides was developed. The reaction occurred under UV irradiation without transition metal catalyst or photocatalyst. A radical pathway via single-electron transfer (SET) of electron donor-acceptor (EDA) complex was proposed based on UV-vis spectroscopy, radical inhibiting and trapping experiments. (Figure presented.).

Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates

A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.

α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines

The readily available α-diazo-β-oxosulfones have been employed, for the first time, in the Wolff cyclocondensation with aromatic amines promoted by 1.5-fold excess of TiCl4. The reaction was found to be general (as illustrated by 15 product examples) and resulted in moderate yields of medicinally relevant sulfonyl 1,2,3-triazoles. Excluding the Lewis acid promoter resulted in a clean and high-yielding formation of α-sulfonyl acetanilides resulting from the thermal Wolff rearrangement and trapping of the ketene intermediate with an aniline molecule.