trifluoromethane sulfonic acid
methanesulfonic acid, 1,1,1-trifluoro-
 
Notes:
deblocking reagent for peptide synthesis. Catalyst used in the prodn. of cocoa butter substitute from palm oil This is a very similar reaction to what would be done if one wanted to create polymers using triflic acid in the synthesis. Other Friedel-Crafts type reactions using triflic acid include cracking of alkanes and alkylation of alkenes which are very important to the petroleum industry. These triflic acid derivative catalysts are very effective in isomerizing straight chain or slightly branched hydrocarbons that can increase the octane rating of a particular petroleum based fuel.; Triflic acid is a hygroscopic, colorless liquid at room temperature. It is soluble in polar solvents such as DMF, DMSO, acetonitrile, and dimethyl sulfone. Addition of triflic acid to polar solvents can be dangerously exothermic.; Trifluoromethanesulfonic acid, also known as triflic acid, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is often regarded as one of the strongest acids, and is one of a number of so-called "superacids". Triflic acid is widely used especially as a catalyst and a precursor in organic chemistry.; With an Ka = 8.0 ×1014 (pKa ~ -15) mol/kg, HOTf qualifies as a superacid. Triflic acid owes many of its useful properties to its great thermal and chemical stability. Both the acid and its conjugate base CF3SO3-, known as triflate, resist oxidation/reduction reactions, whereas many strong acids are oxidizing, e.g. HClO4 and HNO3. The triflate anion is immune to attack by even strong nucleophiles. Because of its resistance to oxidation and reduction, triflic acid is a very useful and versatile reagent. Further recommending its use, triflic acid does not sulfonate substrates, which can be a problem with sulfuric acid, fluorosulfuric acid, and chlorosulfonic acid. Below is a prototypical sulfonation, which HOTf does not undergo:
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CAS Number: 1493-13-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 216-087-5
FDA UNII: JE2SY203E8
Nikkaji Web: J12.301C
Beilstein Number: 1812100
MDL: MFCD00007514
XlogP3-AA: 0.30 (est)
Molecular Weight: 150.07677960
Formula: C H F3 O3 S
NMR Predictor: Predict (works with chrome or firefox)
Category: catalyst in the hydrogenation of fats and oils
 
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FDA Mainterm (SATF):1493-13-6 ; TRIFLUOROMETHANE SULFONIC ACID
FDA Regulation:
FDA PART 173 -- SECONDARY DIRECT FOOD ADDITIVES PERMITTED IN FOOD FOR HUMAN CONSUMPTION
Subpart D--Specific Usage Additives
Sec. 173.395 Trifluoromethane sulfonic acid.
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 1.69600 @  25.00 °C.
Refractive Index: 1.32600 to 1.33100 @  20.00 °C.
Boiling Point: 166.00 °C. @ 760.00 mm Hg
Vapor Pressure: 1.137000 mmHg @ 25.00 °C. (est)
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w): -1.063 (est)
Soluble in:
 water, 1.975e+005 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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BOC Sciences
For experimental / research use only.
PERFLUOROMETHANESULFONIC ACID 95%
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Trifluoromethanesulfonic acid
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For experimental / research use only.
Trifluoromethanesulfonic Acid ≥98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Trifluoromethanesulfonic acid ReagentPlus®, ≥99%
TCI AMERICA
For experimental / research use only.
Trifluoromethanesulfonic Acid >98.0%(T)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: catalyst in the hydrogenation of fats and oils
Recommendation for trifluoromethane sulfonic acid usage levels up to:
 not for fragrance use.
 
Recommendation for trifluoromethane sulfonic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 1493-13-6
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 62406
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 1
 trifluoromethanesulfonic acid
Chemidplus: 0001493136
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References:
 trifluoromethanesulfonic acid
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 1493-13-6
Pubchem (cid): 62406
Pubchem (sid): 135020855
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS): View
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB36577
FooDB: FDB015485
Export Tariff Code: 2904.10.5000
FDA Listing of Food Additive Status: View
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
perfluoromethane sulfonic acid
perfluoromethanesulfonic acid
 methanesulfonic acid, 1,1,1-trifluoro-
 methanesulfonic acid, trifluoro-
 triflic acid
 trifluoromethanesulfonic acid
1,1,1-trifluoromethanesulfonic acid
 trifluoromethanesulphonic acid
 trifluoromethansulfonic acid
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Articles:
PubMed: The role of N-glycosylation in kiwi allergy.
PubMed: Immunochemical approach for zearalenone-4-glucoside determination.
PubMed: Isolation, purification, and identification of protein associated with corn fiber gum.
PubMed: Proteomic analysis of the peritrophic matrix from the gut of the caterpillar, Helicoverpa armigera.
PubMed: TLXI, a novel type of xylanase inhibitor from wheat (Triticum aestivum) belonging to the thaumatin family.
PubMed: Chemical deglycosylation of hen ovomucoid: protective effect of carbohydrate moiety on tryptic hydrolysis and heat denaturation.
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