2,2,2-trifluoroethan-1-ol

• ChemBase ID: 2923
• Molecular Formular: C2H3F3O
• Molecular Mass: 100.0398296
• Monoisotopic Mass: 100.01359938
• SMILES: OCC(F)(F)F
• Canonical SMILES: OCC(F)(F)F
• InChI: InChI=1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2
• InChIKey: RHQDFWAXVIIEBN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,2-trifluoroethan-1-ol
• IUPAC Traditional name: trifluoroethanol
• Synonyms: 2,2,2-Trifluoroethanol, NMR grade; PERFLUORO-1,1-DIHYDROETHANOL; Trifluoroethyl alcohol; 2,2,2-Trifluoroethanol; Trifluoroethanol; 2-Hydroxy-1,1,1-trifluoroethane; (Trifluoromethyl)methanol; 2,2,2-Trifluoroethan-1-ol 99%; TFE; 2,2,2-TRIFLUOROETHANOL; 2,2,2-三氟乙醇, NMR grade; 三氟乙基醇; 2,2,2-三氟乙醇

Database IDs

• CAS Number: 75-89-8; 132248-58-9
• EC Number: 200-913-6
• MDL Number: MFCD00004672
• Beilstein Number: 1733203
• PubChem SID: 24890367; 46505995; 24900367; 24889523; 160966370; 24859618
• PubChem CID: 6409
• CHEBI ID: 42330
• CHEMBL: 116675
• Chemspider ID: 21106169
• DrugBank ID: DB03226
• Wikipedia Title: 2,2,2-Trifluoroethanol

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.4913225
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.43651873
• LogD (pH = 7.4): 0.436484
• Log P: 0.43651918
• Molar Refractivity: 13.7114 cm^3
• Polarizability: 5.0326996 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.61
• LOG S: -0.25
• Solubility (Water): 5.58e+01 g/l

PROPERTIES

Physical Property

• Solubility: Miscible in ethanol; Miscible in water
• Apperance: Colorless liquid
• Melting Point: -43.5 °C; -43.5°C; -44 °C(lit.); -44°C; -44°C
• Boiling Point: 71-78 °C; 74.0 °C; 74-75°C; 74-75°C; 77-80 °C(lit.)
• Flash Point: 28 °C; 29 °C; 29°C; 29°C(84°F); 84.2 °F
• Auto Ignition Point: ~896 °F
• Density: 1.325±0.06 g/mL @ 20 °C, 760 Torr liquid; 1.373; 1.373 g/mL at 25 °C(lit.); 1.38 g/ml; 1.391; 1.391 g/mL at 20 °C
• Refractive Index: 1.2900; 1.2907; n20/D 1.3(lit.)
• Vapor Pressure: 52 mmHg at 25 °C; 70 mmHg ( 25 °C)
• Vapor Density: 3.5 (vs air)
• Absorption Wavelength: λ: 260 nm Amax: ≤0.03; λ: 280 nm Amax: ≤0.02
• pKa: 12.46±0.10 Most Acidic Temp: 25 °C
• Viscosity: 0.9 cSt @ 37.78 °C
• Std enthalpy of combustion: -886.6 kJ/mol
• Std enthalpy of formation: ? kJ/mol
• Std molar entropy: ? J.K^-1.mol^-1

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Flammable/Toxic/Corrosive/Teratogenic/Store under Argon/Moisture Sensitive
• RTECS: KM5250000
• European Hazard Symbols: Flammable (F); X; Harmful (Xn)
• UN Number: 1986; 1987; UN1992
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 3; III
• Australian Hazchem: 3Y
• Risk Statements: 10-20/21/22-37/38-41; R:10-22-36/37; R10, R20/21/22, R36/38, R62
• Safety Statements: 26-36-39; 9-23-26-36/37/39-60; S:9-16-26-36/37/39; S16, S36/37/39, S45
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 127
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Signal Word: Danger
• NFPA704:
  

  3

  2

  1
• Explode Limits: 42 %
• GHS Hazard statements: H226-H301-H312-H315-H318-H331-H335; H301-H311-H331-H315-H335-H318-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1986 3/PG 3

Product Information

• Purity: ≥99.5%; ≥99%; ≥99.0% (GC); ≥99.5%; ≥99.5% (GC); ≥99.8% (GC); 99.5%; 99+%
• Grade: analytical standard for NMR-spectroscopy; eluent additive for LC-MS; for molecular biology; NMR grade; puriss.; ReagentPlus®
• Suitability: passes test for LC-MS
• Impurities: DNases, none detected; insoluble matter, passes filter test; phosphatases, none detected; proteases, none detected; RNases, none detected
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤1 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg
• Shelf Life: (limited shelf life, expiry date on the label)
• λ: neat
• Product Line: BioUltra
• Linear Formula: CF3CH2OH

DETAILS

MP Biomedicals - 05213004

MP Biomedicals Rare Chemical collection

MP Biomedicals - 05219377

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02191330

Colorless liquid Purity: >99.5% Specific gravity: 1.38 g/ml b.p. 73.6°C

DrugBank - DB03226

• Drug Groups: experimental
• Description: A non-aqueous co-solvent that serves as tool to study protein folding. It is also used in various pharmaceutical, chemical and engineering applications. [PubChem]

Sigma Aldrich - 326747

Packaging
100 g in glass bottle

Sigma Aldrich - 96924

Other Notes
Solvent used for sample preparation in electrophoresis1

Sigma Aldrich - T63002

Packaging
25, 100, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Trifluoroethyl esters have also found use as active esters in peptide coupling; see, for example: J. Chem. Soc., Perkin 1, 2867 (1996).
• Useful ionizing solvent, see: Tetrahedron Lett., 2335 (1974), and references therein. Good solvent for oligopeptides with potential as a cosolvent along with proton acceptors such as DMF for peptide coupling reactions: Tetrahedron Lett., 33, 7007 (1992). Compare 1,1,1,3,3,3-Hexafluoro-2-propanol, A12747.
• Effective solvent for uncatalyzed epoxidations of alkenes with hydrogen peroxide (caution! 60%): Synlett, 248 (2001). For a review of fluorinated alcohols as solvents for selective and clean reactions, see: Synlett, 18 (2004).
• Reacts with triphenylphosphine dibromide to give the bis(trifluoroethoxy)phosphorane, which converts alcohols to trifluoroethyl ethers, carboxylic acids to trifluoroethyl esters and aldehydes to bis(trifluoroethyl) acetals: J. Org. Chem., 45, 5052 (1980).
• The stereodirecting effect of the MEM group (see 2-Methoxyethoxymethyl chloride, L01050) has been exploited by Percy et al in the formation of a new fluorine-containing acyl anion equivalent: Tetrahedron, 51, 9201 (1995):
  
• Claisen or Wittig rearrangements of the derived difluoroallyl alcohols can be used in routes to molecules containing a CF₂ group: Tetrahedron, 51, 11327 (1995); J. Org. Chem., 61, 166 (1996), or to monofluorinated vinylic compounds: Tetrahedron Lett., 37, 5183 (1996).