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82113-66-4

N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE, also known as Methanesulfonamide, 1,1,1-Trifluoro-N[(trifluoromethyl)sulfonyl]-N(trimethylsilyl)-, is a colorless liquid with a boiling point of 115°C at 2 Torr. It is a versatile reagent in organic chemistry, particularly as a Lewis acid catalyst for a variety of organic transformations.

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  • 82113-66-4 Structure

  • Basic information

    1. Product Name: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE
    2. Synonyms: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE;[Bis(trifluoromethanesulfonyl)amino]trimethylsilane;TMS Triflimide;[Bis(trifluoromethanesulfonyl)amino]trimethylsilane TMS Triflimide;1,1,1-trifluoro-N-(trifluoroMethylsulfonyl)-N-(triMethylsilyl)MethanesulfonaMide;Methanesulfonamide,1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]-N-(trimethylsilyl)-;N-(Trimethylsilyl)bis(trifluoromethanesulfonyl)imide
    3. CAS NO:82113-66-4
    4. Molecular Formula: C5H9F6NO4S2Si
    5. Molecular Weight: 353.34
    6. EINECS: N/A
    7. Product Categories: Si (Classes of Silicon Compounds);Si-N Compounds;Trimethylsilylazide, etc.
    8. Mol File: 82113-66-4.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 115 °C / 2mmHg
    3. Flash Point: 97.1°C
    4. Appearance: /
    5. Density: 1.543g/cm3
    6. Vapor Pressure: 0.046mmHg at 25°C
    7. Refractive Index: 1.405
    8. Storage Temp.: Freezer
    9. Solubility: soluble in most common organic solvents, commonly used in dichloromethane, toluene, diethyl ether.
    10. PKA: -26.49±0.70(Predicted)
    11. CAS DataBase Reference: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE(CAS DataBase Reference)
    12. NIST Chemistry Reference: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE(82113-66-4)
    13. EPA Substance Registry System: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE(82113-66-4)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 82113-66-4(Hazardous Substances Data)

82113-66-4 Usage

Uses

Used in Organic Chemistry:
N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE is used as a Lewis acid catalyst for various organic transformations. Its ability to accept electron pairs and stabilize intermediates makes it a valuable tool in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE is used as a catalyst in the synthesis of active pharmaceutical ingredients. Its Lewis acid properties enable the formation of new chemical bonds and facilitate the production of desired compounds with high selectivity and yield.
Used in Material Science:
N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE is also employed in material science for the synthesis of advanced materials, such as polymers and composites. Its catalytic properties can be utilized to control the polymerization process and achieve materials with specific properties and applications.
Used in Environmental Applications:
In environmental applications, N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE can be used as a catalyst in the degradation of pollutants and contaminants. Its ability to facilitate chemical reactions can help in breaking down harmful substances and reducing their environmental impact.

Preparation

It is easily prepared in situ through protodesilation by mixing commercially available allyltrimethylsilane (or any TMS enol ether) and Tf2NH. Originally prepared by mixing Tf2NH with trimethylsilane at low temperature or mixing AgNTf2 with TMSCl.

Check Digit Verification of cas no

The CAS Registry Mumber 82113-66-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,1,1 and 3 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 82113-66:
(7*8)+(6*2)+(5*1)+(4*1)+(3*3)+(2*6)+(1*6)=104
104 % 10 = 4
So 82113-66-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H9F6NO4S2Si/c1-19(2,3)12(17(13,14)4(6,7)8)18(15,16)5(9,10)11/h1-3H3

82113-66-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1,1-trifluoro-N-(trifluoromethylsulfonyl)-N-trimethylsilylmethanesulfonamide

1.2 Other means of identification

Product number -
Other names N-trimethylsilyl bis(trifluoromethanesufonyl)imide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:82113-66-4 SDS

82113-66-4Downstream Products

82113-66-4Relevant articles and documents

User friendly synthesis of VogelS silyl sulfinate and its application in quantitative Gc-Ms analysis

Novosjolova, Irina,Turks, Maris

, p. 1251 - 1256 (2015/08/18)

The synthesis of trimethylsilyl 2-methylprop-2-ene-1-sulfinate (Vogel's silyl sulfinate) from methallyltrimethylsilane and SO2 in the presence of Tf2NTMS was developed. The title compound silylates carbohydrates and other polyhydroxylated compounds by producing SO2 and isobutene as gaseous side products. This silylation procedure is perfectly suitable for derivatization and subsequent GC-MS quantitative analysis of ribose and malic acid as representatives of organic polyhydroxylated compounds.

Gold(I)-catalyzed bis-alkynylation reaction of aromatic aldehydes with alkynylsilanes

Rubial, Belen,Ballesteros, Alfredo,Gonzalez, Jose M.

supporting information, p. 3337 - 3343 (2013/12/04)

The first successful gold(I)-catalyzed reaction of aryl aldehydes with trimethyl(arylethynyl)silanes to furnish bis-alkynylated derivatives is reported. Key C-C bond-forming events involved in the catalytic cycle are analyzed. Copyright

A triple-aldol cascade reaction for the rapid assembly of polyketides

Albert, Brian J.,Yamamoto, Hisashi

supporting information; experimental part, p. 2747 - 2749 (2010/07/15)

(Figure Presented) Triple play: The title reaction of 1 with simple aldehydes gives 3,5,7-trisilyloxy aldehydes in high yields and diastereoselectivities with extremely low catalyst loading (see scheme). lodobenzene facil-itates the third aldol reaction by apparently acting as a Lewis base towards the silyl catalyst. Tf=trifluoromethanesulfonyl.

Bistrifluoromethanesulfonimide in the catalytic conjugate allylation of α,β-unsaturated carbonyl compounds

Kuhnert, Nikolai,Peverley, Jonathan,Robertson, Jeremy

, p. 3215 - 3216 (2007/10/03)

Bistrifluoromethanesulfonimide may be used directly to initiate the catalytic conjugate allylation of α,β-unsaturated carbonyl compounds with allyltrimethylsilane; high yields of either silyl enol ethers or δ,ε- unsaturated ketones and esters may be obtai

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