CAS 81290-20-2|Trifluoromethyltrimethylsilane|trimethyl(trifluoromethyl)silane|trifluoromethyltrimethylsilane|Ruppert's Reagent|TFMTMS|(Trifluoromethyl)trimethylsilane|三氟甲基三甲基硅烷溶液|Triflu...

General Information

Structure

Molecular Formula

C₄H₉F₃Si

Molecular Mass

142.1949696

Exact Mass

142.04256148

Charge

InChI

InChI=1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3

InChIKey

MWKJTNBSKNUMFN-UHFFFAOYSA-N

Canonic Smiles

FC([Si](C)(C)C)(F)F

Isomeric Smiles

C[Si](C)(C(F)(F)F)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

3.6948

LogD (pH = 7.4)

3.6948

Log P

3.6948

Molar Refractivity

22.423

Polarizability

10.52733

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

TrifluoromethyltrimethylsilaneRuppert's ReagentTFMTMS(Trifluoromethyl)trimethylsilane三氟甲基三甲基硅烷溶液TrifluoromethyltrimethylsilaneRuppert′s reagentTrimethyl(trifluoromethyl)silane solutionRuppert-Prakash reagent(Trimethylsilyl)trifluoromethane(Trifluoromethyl)trimethylsilane 98%, 0.5M solution in THF(Trifluoromethyl)trimethylsilane 99%(三氟甲基)三甲基硅烷Trimethyl(trifluoromethyl)silaneRuppert’s ReagentRuppert 试剂(Trifluoromethyl)trimethylsilane(Trifluoromethyl)trimethylsilane(Trifluoromethyl)trimethylsilane, 0.5M soln. in THF(三氟甲基)三甲基硅烷, 0.5M THF溶液

IUPAC name

trimethyl(trifluoromethyl)silane

IUPAC Traditional name

trifluoromethyltrimethylsilane

Names and Identifiers

Registration numbers

PubChem SID

248724181609719752486283124889567

MDL Number

Beilstein Number

CAS Number

PubChem CID

Wikipedia Title

Trifluoromethyltrimethylsilane

EC Number

000-000-0

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Apollo Scientific

PC7779

Ruppert's reagent - valuable trifluoromethylating agent of electrophilic compounds. Trifluoromethylates carbonyl compounds in high yield: JACS., 1989, 111, 393

Wikipedia

Trifluoromethyltrimethylsilane

Sigma Aldrich

367737

Application
Nucleophilic addition of the trifluoromethyl group to aldehydes and ketones.7
Reactant for:
• Silver-mediated C-H trifluoromethylation of arenes1
• Preparation of trifluoromethyl ketone analog of L-arginine having contrasting inhibitory activity against human arginase I and histone deacetylase 82
• Organocatalyzed regio- and enantioselective allylic trifluoromethylation of Morita-Baylis-Hillman adducts3
• Palladium-catalyzed oxidative trifluoromethylation of indoles4
• Preparation of 5-HT1A antagonists5
• Used as difluorocarbene source6
Packaging
25 mL in Sure/Seal™
5 mL in glass bottle

488712

Application
Nucleophilic addition of the trifluoromethyl group to aldehydes and ketones.1
Packaging
5, 25 mL in glass bottle

91862

Packaging
10, 50 mL in glass bottle
Application
Reactant for:
• Silver-mediated C-H trifluoromethylation of arenes1
• Preparation of trifluoromethyl ketone analog of L-arginine having contrasting inhibitory activity against human arginase I and histone deacetylase 82
• Organocatalyzed regio- and enantioselective allylic trifluoromethylation of Morita-Baylis-Hillman adducts3
• Palladium-catalyzed oxidative trifluoromethylation of indoles4
• Preparation of 5-HT1A antagonists5
• Used as difluorocarbene source6

91873

Other Notes
Reagent for the nucleophilic trifluoromethylation of various compounds induced by F-,1,2,3,4,5

Molecule Details

References

PubChem Literature

From Data Sources

• In the presence of F^-, aldehydes and ketones give, after hydrolysis of the intermediate silyl ethers, the trifluoromethyl carbinols: J. Am. Chem. Soc., 111, 393 (1989); J. Org. Chem., 56, 984 (1991); Org. Synth. Coll., 9, 711 (1998):

• In the presence of CsF and TMS-imidazole, aldimines are converted to ɑ-trifluoromethyl amines: Tetrahedron Lett., 40, 5475 (1999).

• With a catalytic amount of TBAF, excellent yields of trifluoromethyl ketones can be obtained from methyl esters: Angew. Chem. Int. Ed., 37, 820 (1998).

• For reviews of this and similar reagents, see: Chem. Rev., 97, 757 (1997); J. Fluorine Chem., 112, 123 (2001).

• Similarly, alkyl or aryl thiocyanates are converted to the corresponding trifluoromethyl sulfides in generally good yields: Tetrahedron Lett., 38, 65 (1997). Selenocyanates behave similarly. Trifluoromethylation of aromatics bearing electron-withdrawing groups can be effected in the presence of KF, by displacement of nitro-, cyano- or chloro-substituents: J. Chem. Soc., Perkin 1, 3081 (1998).

• Valuable reagent for trifluoromethylation of electrophilic substrates.

• Alternatively, rapid and efficient trifluoromethylation of carbonyl compounds can be carried out at room temperature in DMSO, in the presence of molecular sieves, without fluoride or other basic catayst: Synlett, 112 (2006). The use of Tri-tert-butylphosphine, 10178 as a catalyst has also been advocated: Synlett, 267 (2006).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

trimethyl(trifluoromethyl)silane

IUPAC Traditional name

trifluoromethyltrimethylsilane

Registration numbers

PubChem SID

248724181609719752486283124889567

MDL Number

Beilstein Number

CAS Number

PubChem CID

Wikipedia Title

Trifluoromethyltrimethylsilane

EC Number

000-000-0

Molecule Details

Apollo Scientific

PC7779

Ruppert's reagent - valuable trifluoromethylating agent of electrophilic compounds. Trifluoromethylates carbonyl compounds in high yield: JACS., 1989, 111, 393

Wikipedia

Trifluoromethyltrimethylsilane

Sigma Aldrich

367737

488712

Application
Nucleophilic addition of the trifluoromethyl group to aldehydes and ketones.1
Packaging
5, 25 mL in glass bottle

91862

91873

Other Notes
Reagent for the nucleophilic trifluoromethylation of various compounds induced by F-,1,2,3,4,5

References

PubChem Literature

From Data Sources

• In the presence of CsF and TMS-imidazole, aldimines are converted to ɑ-trifluoromethyl amines: Tetrahedron Lett., 40, 5475 (1999).

• With a catalytic amount of TBAF, excellent yields of trifluoromethyl ketones can be obtained from methyl esters: Angew. Chem. Int. Ed., 37, 820 (1998).

• For reviews of this and similar reagents, see: Chem. Rev., 97, 757 (1997); J. Fluorine Chem., 112, 123 (2001).

• Valuable reagent for trifluoromethylation of electrophilic substrates.

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:8668