trimethyl(trifluoromethyl)silane

• ChemBase ID: 8668
• Molecular Formular: C4H9F3Si
• Molecular Mass: 142.1949696
• Monoisotopic Mass: 142.04256148
• SMILES: C[Si](C)(C(F)(F)F)C
• Canonical SMILES: FC([Si](C)(C)C)(F)F
• InChI: InChI=1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3
• InChIKey: MWKJTNBSKNUMFN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethyl(trifluoromethyl)silane
• IUPAC Traditional name: trifluoromethyltrimethylsilane
• Synonyms: Ruppert-Prakash reagent; Trifluoromethyltrimethylsilane; Trimethyl(trifluoromethyl)silane solution; Ruppert′s reagent; (Trifluoromethyl)trimethylsilane; Ruppert’s Reagent; Trimethyl(trifluoromethyl)silane; (Trifluoromethyl)trimethylsilane 99%; (Trifluoromethyl)trimethylsilane; Trifluoromethyltrimethylsilane; (Trimethylsilyl)trifluoromethane; (Trifluoromethyl)trimethylsilane 98%, 0.5M solution in THF; Ruppert's Reagent; TFMTMS; (Trifluoromethyl)trimethylsilane, 0.5M soln. in THF; (Trifluoromethyl)trimethylsilane; 三氟甲基三甲基硅烷 溶液; Ruppert 试剂; (三氟甲基)三甲基硅烷; (三氟甲基)三甲基硅烷, 0.5M THF溶液

Database IDs

• CAS Number: 81290-20-2
• EC Number: 000-000-0
• MDL Number: MFCD00145454
• Beilstein Number: 4241868
• PubChem SID: 24872418; 160971975; 24862831; 24889567
• PubChem CID: 552549
• Wikipedia Title: Trifluoromethyltrimethylsilane

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.6948
• LogD (pH = 7.4): 3.6948
• Log P: 3.6948
• Molar Refractivity: 22.423 cm^3
• Polarizability: 10.52733 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: colorless liquid
• Boiling Point: 40 °C; 40°C; 40°C; 54-55 °C; 54-55 °C(lit.); 54-55°C; 54-55°C
• Flash Point: 1.4 °F; -10°C(14°F); -17 °C; -17°C; -20°C
• Density: 0.895; 0.895 g/mL at 25 °C; 0.91 g/mL at 20 °C; 0.962; 0.962 g/mL at 20 °C(lit.); 0.9626 g/cm^3 @ 20 °C
• Refractive Index: 1.330; 1.3305; 1.332; n20/D 1.332; n20/D 1.386
• Vapor Pressure: 10.98 psi ( 55 °C); 2.8 psi ( 20 °C)

Safety Information

• Storage Warning: FLAMMABLE; Highly Flammable/Harmful/Irritant/Hygroscopic/Moisture Sensitive/Light Sensitive/Keep Cold/Store under Argon; Highly Flammable/Keep Cold; Moisture Sensitive
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11; 11-19-36/37; 11-36/37/38
• Safety Statements: 16-26; 16-33; 23-26; 9-16-23-26-33-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H225-H315-H319-H335; H225-H319-H335
• GHS Precautionary statements: P210; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 97%; 98%; 99%
• Concentration: ~2.0 M in THF; 0.5 M in THF; 0.5M soln. in THF
• Grade: purum
• Linear Formula: (CH3)3SiCF3

DETAILS

Apollo Scientific Ltd - PC7779

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

Sigma Aldrich - 488712

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

Sigma Aldrich - 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

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

Sigma Aldrich - 91873

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

REFERENCES

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