428-76-2

Basic information

• Product Name: bis(trifluoromethylsulphonyl)methane
• Synonyms: bis(trifluoromethylsulphonyl)methane;Bis(trifluoromethylsulfonyl)methane;trifluoro(trifluoromethylsulfonylmethylsulfonyl)methane;trifluoro(triflylmethylsulfonyl)methane;Bis(TrifluoroMethanesulfonyl)Methane;Bis(trifluoromethanesulfonyl)methane 97%;Bis(nonafluorobutylsulfonyl)methane
• CAS NO: 428-76-2
• Molecular Formula: C₃H₂F₆O₄S₂
• Molecular Weight: 280.1659992
• EINECS: 207-052-5
• Mol File: 428-76-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 35℃
• Boiling Point: 300.8°Cat760mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.832g/cm³
• Vapor Pressure: 0.00195mmHg at 25°C
• Refractive Index: 1.366
• CAS DataBase Reference: bis(trifluoromethylsulphonyl)methane(CAS DataBase Reference)
• NIST Chemistry Reference: bis(trifluoromethylsulphonyl)methane(428-76-2)
• EPA Substance Registry System: bis(trifluoromethylsulphonyl)methane(428-76-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 428-76-2(Hazardous Substances Data)

Usage

Description

Bis(trifluoromethylsulphonyl)methane, also known as methanesulfonyl bis(trifluoromethylsulfone), is a chemical compound with the formula (CF3SO2)2CH2. It is a solid, non-hygroscopic, and non-oxidizing ligand that is soluble in organic solvents. bis(trifluoromethylsulphonyl)methane is known for its stability and reactivity in various chemical reactions, making it a valuable component in the field of chemistry.

Uses

Used in Lanthanide Chemistry:
Bis(trifluoromethylsulphonyl)methane is used as a ligand for Lanthanide chemistry. Its non-hygroscopic and non-oxidizing properties, along with its solubility in organic solvents, make it an ideal candidate for use in the synthesis and stabilization of Lanthanide complexes. These complexes have various applications in fields such as catalysis, materials science, and pharmaceuticals.
Used in Catalyst Synthesis:
In the field of catalysis, bis(trifluoromethylsulphonyl)methane serves as a valuable ligand for the development of novel catalysts. Its unique properties allow for the creation of catalysts with enhanced stability and reactivity, which can be applied in various chemical reactions, including organic synthesis and polymerization processes.
Used in Materials Science:
Bis(trifluoromethylsulphonyl)methane is also utilized in the development of advanced materials. Its ability to form stable complexes with Lanthanides can lead to the creation of materials with unique optical, electronic, and magnetic properties. These materials can be used in various applications, such as sensors, electronic devices, and energy storage systems.
Used in Pharmaceutical Applications:
Due to its stability and reactivity, bis(trifluoromethylsulphonyl)methane can be employed in the synthesis of pharmaceutical compounds. Its use as a ligand in Lanthanide complexes can lead to the development of new drugs with improved properties, such as enhanced bioavailability and targeted delivery to specific tissues or organs.

InChI:InChI=1/C3H2F6O4S2/c4-2(5,6)14(10,11)1-15(12,13)3(7,8)9/h1H2

Upstream product

• 917-64-6 methyl magnesium iodide 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1822-00-0 trimethylsilylmethyllithium 
• 75-16-1 methylmagnesium bromide 
• 40906-88-5 dibromo bis(trifluoromethanesulphonyl) methane 
• 34241-39-9 azobisisobutyronitrile 
• 108-88-3 toluene 
• 676-58-4 methylmagnesium chloride 
• 75-38-7 Vinylidene fluoride 
• 84132-17-2 Ethyl 2,2-Bis<(trifluoromethyl)thio>acetate 
• 84132-18-3 2,2-Bis<(trifluoromethyl)thio>acetic acid 

Downstream Products

• 31139-48-7 (2,2-bis(trifluoromethanesulfonyl)ethyl)benzene 
• 145124-59-0 1-tolyl-2,2-bis(trifluoromethanesulfonyl)ethylene 
• 58558-79-5 p-(N,N-dimethylamino)-β,β-bis(trifluoromethylsulfonyl)styrene 
• 60805-12-1 tris-(trifluoromethanesulfonyl)methane acid 
• 114634-82-1 (P((C₆H₅)O)3)4Rh⁽¹⁺⁾*(HC(SO₂CF₃)2)^(1-)=(P(C₆H₅)3O₃)4RhHC(SO₂CF₃)2 
• 114634-87-6 {trans-(Rh(PPh₃)2(CO)2)}*{(HC(SO₂CF₃)2)} 
• 114634-79-6 ((C₆H₅)2PC₂H₂P(C₆H₅)2)2CoH₂⁽¹⁺⁾*(HC(SO₂CF₃)2)^(1-)=((C₆H₅)4P₂C₂H₂)2CoH₂HC(SO₂CF₃)2 
• 114634-80-9 (P(C₆H₅)3)3Ir(CO)H₂⁽¹⁺⁾*(HC(SO₂CF₃)2)^(1-)=P₃(C₆H₅)9COIrH₂HC(SO₂CF₃)2 
• 98837-97-9 {(triphenylphosphine)3rhodium(carbonyl)}{CH(SO₂CF₃)2} 
• 133270-36-7 {((C₆H₅)3P)3NiH}⁽¹⁺⁾*{HC(SO₂CF₃)2}^(1-)={((C₆H₅)3P)3NiH}{HC(SO₂CF₃)2} 
• 133270-31-2 {((C₆H₅)3P)3PtH}⁽¹⁺⁾*{HC(SO₂CF₃)2}^(1-)={((C₆H₅)3P)3PtH}{HC(SO₂CF₃)2} 
• 133294-52-7 {((C₆H₅)3P)3PdH}⁽¹⁺⁾*{HC(SO₂CF₃)2}^(1-)={((C₆H₅)3P)3PdH}{HC(SO₂CF₃)2} 
• 133270-38-9 {((C₆H₅)2PCH₃)3PdH}⁽¹⁺⁾*{HC(SO₂CF₃)2}^(1-)={((C₆H₅)2PCH₃)3PdH}{HC(SO₂CF₃)2} 
• 103712-02-3 (P(C₆H₅)3)2Pt(C₆H₅CCHC₆H₅)(HC(SO₂CF₃)2) 

Relevant articles and documents

Structures and conformations of trifluoromethanesulfonic anhydride, (CF3so2)2O, and bis(trifluoromethylsulfonyl)difluoromethane, (CF3so2)2CF2

The geometric structures and conformational properties of trifluoromethanesulfonic anhydride, (CF3SO2)2O, and bis(trifluoromethylsulfonyl)difluoromethane, (CF3SO2)2CF2 have been studied by gas electron diffraction (GED) and ab initio calculations (HF/3-21G*). The calculations predict for both systems two stable conformera with C2 symmetry and one with C1 symmetry. In both compounds structures with C2 symmetry and dihedral angles SOSC ≈ 100° ((CF3SO2)2O) and SCSC ≈ 150° ((CF3SO2)2CF2) are lowest in energy. According to the GED analyses the dominant conformer of (CF3SO2)2O possesses C2 symmetry with SOSC dihedral angles of 99.1(14)°. The presence of up to 30% of the two other conformers cannot be excluded; for (CF3SO2)2CF2 only one conformer with C2 symmetry and SCSC dihedral angles of 143(2)° is observed. A complete set of geometric parameters is given.

The addition of (CF3SO2)2CHBr to vinylidene fluoride

It has been found that a mixture of (CF3SO2)2CH2 and (CF3SO2)2CBr2 can be used instead of (CF3SO2)2CHBr in the radical addition to H2C{double bond, long}CF2; the 1:1 and 1:2 adducts have been isolated and characterized. An improved synthesis of (CF3SO2)2CBr2 is also reported.

Pyrolysis of benzenediazonium bis(trifluoromethanesulfonyl)methide

The pyrolysis of benzenediazonium bis(trifluoromethanesulfonyl)methide in the absence of solvents did not give the carbon arylation product, PhCH(SO2CF3)2, but the oxygen phenylation product, PhO(CF3)S(O)=CHSO2CF3, in good yield. In contrast, the pyrolysis of the same compound in acetonitrile gave the acetonitrile-inserted compound, PhNH(Me)C=C(SO2CF3)2, quantitatively.