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CAS 289706-46-3

4-[2,2,2-Trifluoro-1-[(trimethylsilyl)oxy]ethyl]morpholine TCI T3597

4-[2,2,2-Trifluoro-1-[(trimethylsilyl)oxy]ethyl]morpholine TCI T3597

Chemical Identity

CAS No.
289706-46-3
PubChem
CID 11149558·SID 354335215
Formula
C9H18F3NO2Si
Molecular weight
257.32 g/mol
Purity
>95.0%(GC)
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
trimethyl-(2,2,2-trifluoro-1-morpholin-4-ylethoxy)silane
SMILES
C[Si](C)(C)OC(C(F)(F)F)N1CCOCC1
InChIKey
ZEPGTXLXUWKETC-UHFFFAOYSA-N
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4-[2,2,2-Trifluoro-1-[(trimethylsilyl)oxy]ethyl]morpholine (CAS 289706-46-3) is a high-quality chemical from TCI, supplied as GC Grade / for Synthesis.

Application: Used as a silylating reagent for hydroxyl-group protection and GC derivatisation.

Specifications:

  • Molecular formula: C9H18F3NO2Si
  • CAS number: 289706-46-3
  • Purity: >95.0%(GC)
  • TCI product code: T3597

Available from AMI Scientific, the authorised TCI distributor in Indonesia. Contact us for pricing and stock availability — we ship throughout Indonesia.

Advantages (TCI brochure)

  • Air-stable liquid
  • Usable as a trifluoromethyl anion equivalent for nucleophilic additions
  • Applicable to cross coupling using copper catalyst

From the TCI brochure

  • Nucleophilic addition to carbonyl compounds (R1 = aryl, heteroaryl; R2 = H, aryl, heteroaryl), catalytic CsF, DME, 80 °C
  • Cross coupling with aryl iodides, catalytic CuI and 1,10-phenanthroline, CsF, diglyme, 80 °C

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Data from the TCI brochure

Yield, nucleophilic addition (product with two phenyl groups, drawn)Y. 75% (cat. CsF [C2204], DME, 80 °C)
Yield, nucleophilic addition (product with alkenyl and two phenyl groups, drawn)Y. 70% (cat. CsF [C2204], DME, 80 °C)
Yield, nucleophilic addition (thienyl product, drawn)Y. 80% (cat. CsF [C2204], DME, 80 °C)
Yield, cross coupling (nitro-aryl product, drawn)Y. 77% (cat. CuI, cat. 1,10-phenanthroline, CsF, diglyme, 80 °C)
Yield, cross coupling (ethoxy-aryl product, drawn)Y. 54% (cat. CuI, cat. 1,10-phenanthroline, CsF, diglyme, 80 °C)
Yield, cross coupling (methyl-thienyl product, drawn)Y. 75% (cat. CuI, cat. 1,10-phenanthroline, CsF, diglyme, 80 °C)

Source: TCI brochure RR121 (2019-08-09)

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References cited in the TCI brochure

  1. Hideaki Kondo. Copper‐Catalyzed Aromatic Trifluoromethylation via Group Transfer from Fluoral Derivatives Advanced Synthesis & Catalysis, 2011. doi:10.1002/adsc.201000825