2,2,2-trifluoroethyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 99599
• Molecular Formular: C9H9F3O3S
• Molecular Mass: 254.2261696
• Monoisotopic Mass: 254.02244981
• SMILES: S(=O)(=O)(c1ccc(cc1)C)OCC(F)(F)F
• Canonical SMILES: FC(COS(=O)(=O)c1ccc(cc1)C)(F)F
• InChI: InChI=1S/C9H9F3O3S/c1-7-2-4-8(5-3-7)16(13,14)15-6-9(10,11)12/h2-5H,6H2,1H3
• InChIKey: IGKCQDUYZULGBM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,2-trifluoroethyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: 2,2,2-trifluoroethyl 4-methylbenzenesulfonate
• Synonyms: 2,2,2-Trifluoroethyl 4-toluenesulphonate 98%; p-Toluenesulfonic acid 2,2,2-trifluoroethyl ester; 2,2,2-trifluoroethyl 4-methylbenzenesulfonate; 2,2,2-Trifluoroethyl p-toluenesulfonate; 2,2,2-三氟乙基 对甲苯磺酸酯; 2,2,2-三氟乙基对甲苯磺酸酯

Database IDs

• CAS Number: 433-06-7
• EC Number: 207-085-5
• MDL Number: MFCD00000443
• Beilstein Number: 2699394
• PubChem SID: 162085862; 24850693
• PubChem CID: 67942

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.0006309
• LogD (pH = 7.4): 3.0006309
• Log P: 3.0006309
• Molar Refractivity: 51.6541 cm^3
• Polarizability: 20.136341 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 36-38 °C(lit.); 36-38°C; 37-42°C
• Boiling Point: 87-92 °C/0.1 mmHg(lit.); 87-92°C/0.1mm; 89-90°C/0.1mm
• Flash Point: >110°C; >110°C(230°F); 113 °C; 235.4 °F
• Hydrophobicity(logP): 2.608

Safety Information

• Storage Warning: Irritant; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 98%; 98+%; 99%
• Linear Formula: CH3C6H4SO3CH2CF3

DETAILS

Apollo Scientific Ltd - PC7376

Useful reagent for introduction of trifluoroethyl group

Sigma Aldrich - 177822

Packaging
50 g in glass bottle

REFERENCES

• Metallation by LDA leads to 2,2-difluoro-1-tosyloxyvinyllithium, which adds quantitatively to carbonyl groups. Acid hydrolysis leads to ɑ-tosyloxy acrylates, which can be hydrolyzed to ɑ-keto acids by base: Tetrahedron Lett., 4809 (1978):
  
• n-BuLi at -78^o has also been used by Ichikawa's group to generate the vinyllithium intermediate, which undergoes boron or copper mediated reactions yielding 2,2-difluorovinyl ketones and other products. See, e.g.: Tetrahedron Lett., 33, 337 (1992); Tetrahedron, 50, 11637 (1994); J. Org. Chem., 60, 2320 (1995).
• Alkylating agent for introduction of the trifluoroethyl group.