ethyl 2,2,2-trifluoroacetate

• ChemBase ID: 8129
• Molecular Formular: C4H5F3O2
• Molecular Mass: 142.0765096
• Monoisotopic Mass: 142.02416406
• SMILES: C(C(=O)OCC)(F)(F)F
• Canonical SMILES: CCOC(=O)C(F)(F)F
• InChI: InChI=1S/C4H5F3O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
• InChIKey: STSCVKRWJPWALQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2,2,2-trifluoroacetate
• IUPAC Traditional name: trifluoroethyl acetate
• Synonyms: Trifluoroacetic acid ethyl ester; Ethyl trifluoroacetate; Ethyl trifluoroacetate 99%; Ethyl trifluoroacetate; Ethyl 2,2,2-trifluoroacetate; 三氟醋酸乙酯; 三氟乙酸乙酯

Database IDs

• CAS Number: 383-63-1
• EC Number: 206-851-6
• MDL Number: MFCD00000419
• Beilstein Number: 1761411
• PubChem SID: 24889534; 24894596; 160971436
• PubChem CID: 9794

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.411685
• LogD (pH = 7.4): 1.411685
• Log P: 1.411685
• Molar Refractivity: 23.1716 cm^3
• Polarizability: 8.734279 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: <-78°C; -78°C
• Boiling Point: 60-62 °C(lit.); 60-62°C; 60-62°C
• Flash Point: -1 °C; -1°C; -1°C(30°F); 30.2 °F
• Density: 1.192; 1.194; 1.194 g/mL at 25 °C(lit.)
• Refractive Index: 1.3070; 1.3072; n20/D 1.307(lit.); n20/D 1.308

Safety Information

• Storage Warning: FLAMMABLE, CORROSIVE; Flammable/Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); Harmful (Xn)
• UN Number: 1993; UN2924
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-22-37/38-41; 11-34; R:10
• Safety Statements: 16-26-33-36/37/39-45; 9-16-26-36/39; S:9-16-29
• TSCA Listed: true; 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H315-H318-H335; H225-H314-H318
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (GC); 97%; 99%
• Grade: puriss.
• Linear Formula: CF3COOC2H5

DETAILS

MP Biomedicals - 05213862

MP Biomedicals Rare Chemical collection

Sigma Aldrich - E50000

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 91710

Other Notes
Reagent for the mild N-trifluoroacetylation of amino acids and peptides1; synthesis of trifluoromethyl ketones from Grignard reagents2

REFERENCES

• Esters of perfluoroalkyl carboxylic acids undergo Wittig reactions, for example with the ylide from (3-Phenylpropyl)triphenylphosphonium bromide, A12669, leading to 1-perfluoroalkyl enol ethers, which are useful precursors of various fluorinated derivatives: J. Org. Chem., 57, 3807 (1992); Org. Synth., 75, 153 (1997):
  
• Reagent for selective trifluoroacetylation of amines. Primary amines can be protected in the presence of secondary, and diamines selectively monoprotected. Primary amines can also be differentiated in terms of steric hindrance: Tetrahedron Lett., 36, 7357 (1995).