91862

Trimethyl(trifluoromethyl)silane solution

2 M in THF

• Synonym(s): (Trifluoromethyl)trimethylsilane, Ruppert′s reagent, Ruppert-Prakash reagent, TFMTMS, Trifluoromethyltrimethylsilane
• Linear Formula: (CH₃)₃SiCF₃
• CAS Number: 81290-20-2
• Molecular Weight: 142.19
• Beilstein/REAXYS Number: 4241868
• MDL number: MFCD00145454
• UNSPSC Code: 12352101
• PubChem Substance ID: 57653455
• NACRES: NA.22

Properties

• form: liquid
• reaction suitability: reaction type: C-C Bond Formation
• IVD: for in vitro diagnostic use
• concentration: 2 M in THF
• refractive index: n20/D 1.386
• density: 0.91 g/mL at 20 °C
• SMILES string: C[Si](C)(C)C(F)(F)F
• InChI: 1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3
• InChI key: MWKJTNBSKNUMFN-UHFFFAOYSA-N

Description

General description

Trimethyl(trifluoromethyl)silane (TMSCF₃) is also called as Ruppert-Prakash fluorination reagent. It is extensively used for the synthesis of trifluoromethyl-containing compounds.

Application

Reactant for:

• Silver-mediated C-H trifluoromethylation of arenes
• Preparation of trifluoromethyl ketone analog of L-arginine having contrasting inhibitory activity against human arginase I and histone deacetylase 8
• Organocatalyzed regio- and enantioselective allylic trifluoromethylation of Morita-Baylis-Hillman adducts
• Palladium-catalyzed oxidative trifluoromethylation of indoles
• Preparation of 5-HT1A antagonists

• Used as difluorocarbene source

TMSCF₃ can be used as a reagent for:

• Conversion of aromatic aldehydes to difluoromethylated products.
• C-H trifluoromethylation of arenes, terminal alkynes, tertiary amines, heteroarenes, allylic, and terminal alkenes using metal catalyst or metal free oxidative trifluoromethylation reaction.

It can also be used in trifluoromethylation of:

• Non-activated aldimines.
• Heterocumulenes.
• Azomethine imines.

Safety Information

• pictograms: GHS02,GHS08,GHS07
• signalword: Danger
• hcodes: H225,H302,H319,H335,H351
• pcodes: P210 - P280 - P301 + P312 + P330 - P305 + P351 + P338 - P370 + P378 - P403 + P235
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
• target_organs: Respiratory system
• supp_hazards: EUH019
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 1.4 °F
• flash_point_c: -17 °C
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter