8.21166

Trifluoromethanesulfonic acid

for synthesis

• Sinónimos: Trifluoromethanesulfonic acid, Triflic acid, TFMS
• Fórmula empírica (notación de Hill): CHF₃O₃S
• Número de CAS: 1493-13-6
• Peso molecular: 150.08
• Número MDL: MFCD00007514
• Código UNSPSC: 12352106
• Número índice de la CE: 216-087-5
• NACRES: NA.22

Propiedades

• grado: for synthesis; synthesis grade
• Nivel de calidad: 200
• presión de vapor: 10 hPa ( 55 °C)
• Formulario: liquid
• potencia: 1605 mg/kg LD₅₀, oral (Rat); >2000 mg/kg LD₅₀, skin (Rat)
• pH: <1 ( in H₂O)
• bp: 162 °C/1013 hPa
• densidad: 1.71 g/cm³ at 20 °C
• temp. de almacenamiento: 2-30°C
• cadena SMILES: [Ba+2].FC(F)(F)[S](=O)(=O)[O-].FC(F)(F)[S](=O)(=O)[O-]
• InChI: 1S/2CHF3O3S.Ba/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2
• Clave InChI: DXJURUJRANOYMX-UHFFFAOYSA-L

Descripción

Descripción general

Trifluoromethanesulfonic acid (also known as Triflic acid, TFMSA or TfOH) is an organic acid that is commonly used as a reagent in organic synthesis due to its strong Bronsted acidity, finding applications in catalysis, N-protection, dehydration, activation, and addition reactions.^[1],[2] TFMSA is also used for global deprotection and cleavage in Boc SPPS.[3]

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Boc SPPS

Literature references:
^[1] L. R. Subramanian, et al. (2001) Encyclopedia of Reagents for Organic Synthesis.
^[2] R. D. Howells & J. D. Mc Cown JD (1977) Chem. Rev., 77, 69.
^[3] J. Stewart, J. Young in “Solid Phase Peptide Synthesis”, Pierce Chemical Company, Rockford, 1984.

Aplicación

Recent applications of trifluoromethanesulfonic acid include:

• A dehydrating agent for the conversion of secondary alcohols to alkene, or the preparation of anhydrides from carboxylic acids.[4]
• An acid catalyst in the synthesis of carbohydrates and glycosides.[5]
• An activating agent for the activation of carboxylic acids and can be used for the synthesis of carboxylic acid derivatives such as esters, amides, and anhydrides.[6]

Información de seguridad

• Pictogramas: GHS05,GHS07
• Palabra de señalización: Danger
• Frases de peligro: H290 - H302 - H314 - H335
• Consejos de prudencia: P234 - P261 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• Clasificaciones de peligro: Acute Tox. 4 Oral - Met. Corr. 1 - Skin Corr. 1B - STOT SE 3
• Órganos de actuación: Respiratory system
• Código de clase de almacenamiento: 8A - Combustible, corrosive hazardous materials
• Clase de riesgo para el agua (WGK): WGK 1
• Punto de inflamabilidad (°F): 332.1 °F - Pensky-Martens closed cup
• Punto de inflamabilidad (°C): > 166.7 °C - Pensky-Martens closed cup