(Difluoromethyl)trimethylsilane

Base Information

• Chemical Name: (Difluoromethyl)trimethylsilane
• CAS No.: 65864-64-4
• Molecular Formula: C4H10F2Si
• Molecular Weight: 124.206
• Hs Code.: 29319090
• European Community (EC) Number: 804-145-8
• DSSTox Substance ID: DTXSID20457496
• Nikkaji Number: J1.915.207C
• Mol file: 65864-64-4.mol

Synonyms:(difluoromethyl)trimethylsilane;65864-64-4;Difluoromethyltrimethylsilane;Silane, (difluoromethyl)trimethyl-;difluoromethyl(trimethyl)silane;Difluoromethyl-trimethyl-silane;(Difluoromethyl)(trimethyl)silane;Difluoromethyl)trimethylsilane;Me3Sicf2H;trimethyl(difluoromethyl)silane;SCHEMBL4854565;(Difluoromethyl)trimethyl-silane;AMY6657;DTXSID20457496;BCP32220;BBL103460;MFCD19381658;STL557270;AKOS015913928;SB38170;AS-53422;D4364;EN300-106165;P16466;(Difluoromethyl)trimethylsilane, >=98.0% (GC);J-501802;(Difluoromethyl)trimethylsilane

Chemical Property of (Difluoromethyl)trimethylsilane

Chemical Property:

• Refractive Index: 1.3560-1.3600
• Boiling Point: 52°C(lit.)
• Flash Point: -17℃
• PSA: 0.00000
• Density: 0.877±0.06 g/cm3(Predicted)
• LogP: 2.54880
• Storage Temp.: 0-10°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 124.05198318
• Heavy Atom Count: 7
• Complexity: 55.2

Purity/Quality:

97% ^*data from raw suppliers

(Difluoromethyl)trimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 2423974
• Hazard Codes: F
• Statements: 11
• Safety Statements: 15-7-35

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C(F)F
• General Description: Silane, (difluoromethyl)trimethyl- (Me₃SiCF₂H) is an effective nucleophilic difluoromethylating agent for carbonyl compounds and imines when activated by a suitable Lewis base, enabling reactions at ambient or low temperatures. Its utility was demonstrated in the direct difluoromethylation of aldehydes, ketones, and sulfinyl imines, overcoming prior assumptions about its inefficiency. The success of the reaction depends on the choice of Lewis base initiator and solvent, highlighting its potential for applications in life and material sciences.

Technology Process of (Difluoromethyl)trimethylsilane

There total 4 articles about (Difluoromethyl)trimethylsilane 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:

chloro-trimethyl-silane (75-77-4) + [chloro(difluoro)methyl]trimethylsilane (115262-00-5) → trimethylsilyl fluoride (420-56-4) + trimethyl(difluoromethyl)silane (65864-64-4) + bis(trimethylsilyl)difluoromethane (86847-53-2) + 1,2-bis(trimethylsilyl)-1,1,2,2-tetrafluoroethane (186824-44-2)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutylammomium bromide; In tetrahydrofuran; Mechanism; Product distribution; electrolysis, Al anode, Ni cathode, other reagents: tris(3,6-dioxaheptyl)amine, tetrabutylammonium hexafluorophosphate, magnesium, various current density, various reactant ratios;

DOI:10.1021/ja962990n

Reference yield:

(difluoromethyl)silane (10112-10-4) → methyl fluorosilane (753-44-6) + methyldifluorosilane (420-34-8) + methyltrifluorosilane (373-74-0) + trimethyl(difluoromethyl)silane (65864-64-4)

Guidance literature:

at 210 - 220 ℃; for 7h; Title compound not separated from byproducts;

DOI:10.1016/0022-328X(92)80068-9

Reference yield:

benzaldehyde (100-52-7) + bis(trimethylsilyl)difluoromethane (86847-53-2) → Difluoromethane (75-10-5) + trimethyl(difluoromethyl)silane (65864-64-4) + (2,2-Difluoro-2-trimethylsilanyl-1-trimethylsilanyloxy-ethyl)-benzene

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,2-dimethoxyethane; for 24h; Mechanism; Product distribution; Ambient temperature; other aldehydes and ketones, other reagents: KF, N-methylpyrrolidinone, other solvent: THF;

DOI:10.1021/ja962990n

upstream raw materials:

(difluoromethyl)silane

chloro-trimethyl-silane

[chloro(difluoro)methyl]trimethylsilane

benzaldehyde

Downstream raw materials:

C₁₃H₁₉F₂NO₂S

C₁₃H₁₉F₂NOS

(R)-N-((S)-1-(4-bromophenyl)-2,2-difluoroethyl)-2-methylpropane-2-sulfinamide

C₁₅H₁₄F₂O

Refernces

Efficient and direct nucleophilic difluoromethylation of carbonyl compounds and imines with Me₃SiCF₂H at ambient or low temperature

10.1021/ol202208b

The research focuses on the development of an efficient and direct nucleophilic difluoromethylation method for carbonyl compounds and imines using Me3SiCF2H as the difluoromethylating agent. The study challenges the previous belief that Me3SiCF2H is inefficient, demonstrating that with the proper Lewis base activator, it can effectively difluoromethylate various aldehydes, ketones, and imines at room temperature or even at -78°C. The experiments involved the use of different Lewis base initiators, solvents, and reaction conditions to optimize the reaction. Key reactants included Me3SiCF2H, aldehydes, ketones, and N-tert-butylsulfinyl imines, with initiators such as KF/18-crown-6, TBAT, CsF, and tBuOK. The analyses used to assess the success of the reactions included isolated yields of products, diastereomeric ratios determined by 19F NMR spectroscopy, and comparisons with previous methods. The study concluded that the use of a proper Lewis base and solvent is crucial for activating the Si-CF2H bond, paving the way for a general and direct nucleophilic difluoromethylation method applicable in life science and material science fields.