Trifluoromethanesulfonic acid

Iupac Name：trifluoromethanesulfonic acid

Molecular Weight：150.07705

Modify Date.: 2022-11-29 08:30

Introduction: Trifluoromethanesulfonic acid, also known as triflic acid, TFMS, TFSA, 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". it is used in the manufacture of pharmaceuticals, agricultural chemicals and polymers. The anhydrous form is widely used in fine chemical synthesis. It is non-oxidizing, has a high thermal stability, and is resistance to both oxidation and reduction, which makes it one of the more useful compounds in the super acids class. In the pharma industry, it is used to make a number of drug classes, including nucleosides, antibiotics, steroids, proteins and glycosides. Triflic anhydride reacts readily with water and has an unfavorable toxicity profile. View more+

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1. Names and Identifiers

1.1 Name: Trifluoromethanesulfonic acid
1.2 Synonyms: 1,1,1-trifluoromethanesulfonic acid EINECS 216-087-5 FC-24 Fluorad FC-24 HOTf Methanesulfonic acid, 1,1,1-trifluoro- Methanesulfonic acid, trifluoro- METHANESULFONIC ACID,TRIFLUORO MFCD00007514 PERFLUOROMETHANESULFONIC ACID PFC-MS tfmsa TfOH Triflic acid trifluoromethanesulfonic trifluoromethane-sulfonic acid trifluoro-methanesulfonicaci TRIFLUOROMETHANESULPHONIC ACID trifluoromethansulfonic acid Trifluoromethylsulfonic acid trifluorormethanesulfonic acid

1.3 CAS No.: 1493-13-6

1.4 CID: 62406

1.5 EINECS(EC#): 216-087-5

1.6 Molecular Formula: CHF3O3S (isomer)

1.7 Inchi: InChI=1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)

1.8 InChkey: ITMCEJHCFYSIIV-UHFFFAOYSA-N

1.9 Canonical Smiles: C(F)(F)(F)S(=O)(=O)O

1.10 Isomers Smiles: C(F)(F)(F)S(=O)(=O)O

2. Properties

2.1 Density: 1.696

2.1 Melting point: -40℃

2.1 Boiling point: 162℃

2.1 Refractive index: 1.326-1.33

2.1 Flash Point: None

2.2 Precise Quality: 149.96000

2.2 PSA: 62.75000

2.2 logP: 1.47480

2.2 Solubility: Miscible in H2O

2.3 VaporDensity: 5.2 (vs air)

2.4 Appearance: Solid

2.5 Storage: Hygroscopic. Store under Nitrogen. Ambient temperatures.

2.6 Chemical Properties: Trifluoromethanesulfonic acid is a hygroscopic, colorless liquid at room temperature. It is soluble in polar solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetonitrile, and dimethyl sulfone. Addition of triflic acid to polar solvents can be dangerously exothermic.Trifluoromethanesulfonic 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: C6H6 + H2SO4 → C6H5(SO3H) + H2O.

2.7 Color/Form: slightly brown

2.8 PH: <1 (H2O)

2.9 pKa: -14(at 25℃)

2.10 Water Solubility: SOLUBLE

2.11 Stability: Stable. Incompatible with acids, alkalis, metals.

2.12 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Definition: ChEBI: A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.

3.2 Usage: It is used for organic synthesis, widely used in pharmaceutical and chemical industries, such as nucleosides, antibiotics, steroids, protein, sugar, vitamins synthesis, silicone rubber modification. Isomerization and alkylation of the catalyst, the preparation of 2, 3-dihydro-2-indanone, tetralone, glycosides in the removal of glycoproteins.

4. Safety and Handling

4.1 Symbol: GHS02, GHS05

4.1 Hazard Codes: C

4.1 Signal Word: Danger

4.1 Risk Statements: R21/22;R35

4.1 Safety Statements: S26;S36/37/39;S45

4.1 Packing Group: II

4.1 Hazard Class: 8

4.1 Hazard Declaration: H226-H314

4.1 RIDADR: UN 3265

4.1 Safety Profile: A corrosive irritant tothe skin, eyes, and mucous membranes. Astrong acid. Violent reaction with acylchlorides or aromatic hydrocarbons evolvestoxic hydrogen chloride gas. When heated todecomposition it emits toxic fumes of FandSOx. See also FLUORIDES. Trifluoromethanesulfonic acid Preparation Products And Raw materials Preparation Products

4.2 Caution Statement: P280-P305 + P351 + P338-P310

4.2 WGK Germany: 2

4.2 RTECS: PB2771000

4.2 Safety: Hazard Codes:? C
Risk Statements:
10:? Flammable?
35:? Causes severe burns?
21/22:? Harmful in contact with skin and if swallowed?
Safety Statements:
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
45:? In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)?
36/37/39:? Wear suitable protective clothing, gloves and eye/face protection?

4.3 Sensitive: Hygroscopic

4.4 Specification: ?Trifluoromethanesulfonic acid , its cas register number is 1493-13-6. It also can be called Methanesulfonic acid, 1,1,1-trifluoro- ; and Triflic acid . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, p-Tolualdehyde (CAS NO.620-23-5) could be stable under normal temperatures and pressures. It?absorbs moisture or water from the air, and is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products:?carbon monoxide, oxides of sulfur, carbon dioxide, hydrogen fluoride gas.

4.5 Toxicity: ?p-Tolualdehyde (CAS NO.620-23-5) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. And the toxicological properties have not been fully investigated.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Corrosive to metals, Category 1

Acute toxicity - Oral, Category 4

Skin corrosion, Category 1B

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H290 May be corrosive to metals H302 Harmful if swallowed H314 Causes severe skin burns and eye damage H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P234 Keep only in original packaging. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P390 Absorb spillage to prevent material damage. P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P406 Store in a corrosion resistant/...container with a resistant inner liner. P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

1493-13-6Total: 58 Synthesis Route

75-46-7 68 Suppliers

1493-13-6 266 Suppliers

Literatures:
Science, , vol. 338, # 6112 p. 1324 - 1327
Yield: null

335-05-7 16 Suppliers

1493-13-6 266 Suppliers

Literatures:
Gramstad, T.; Haszeldine, R. N. Journal of the Chemical Society, 1956 , p. 173 - 180
Yield: ~51%

425-75-2 62 Suppliers

1493-13-6 266 Suppliers

Literatures:
Journal of the Chemical Society, , p. 4069,4079
Yield: null

View all

7. Precursor and Product

precursor:

425-75-2

456-56-4

54010-75-2

2794-60-7

2926-27-4

75-46-7

2923-17-3

78522-65-3

358-23-6

421-82-9

74427-22-8

3592-44-7

65269-94-5

65310-39-6

65269-92-3

49789-04-0

78522-66-4

333-27-7

675-63-8

13937-78-5

335-05-7

2926-29-6

421-83-0

View all

product :

425-75-2

54010-75-2

2794-60-7

2926-27-4

3855-45-6

27607-77-8

358-23-6

27607-78-9

62861-51-2

91190-30-6

55120-75-7

64821-69-8

36967-85-8

68725-14-4

32578-29-3

76-16-4

68602-57-3

49789-04-0

333-27-7

335-05-7

3582-05-6

View all

8. Other Information

8.0 Mesh Entry Terms: AgOTf cpd

8.1 Production: < 25,000 lb

8.2 Manufacturing Info: Miscellaneous manufacturing|Methanesulfonic acid, 1,1,1-trifluoro-: ACTIVE

8.3 General Description: Trifluoromethanesulfonic acid is a strong organic acid. It can be prepared by reacting bis(trifluoromethylthio)mercury with H₂O₂. On mixing with HNO₃, it affords a nitrating reagent (a nitronium salt). This reagent is useful for the nitration of aromatic compounds. Its dissociation in various organic solvents has been studied.

8.4 Merck: 14,9676

8.5 BRN: 1812100

8.6 Description: Trifluoromethanesulfonic acid, also known as triflic acid, TFMS, TFSA, 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". it is used in the manufacture of pharmaceuticals, agricultural chemicals and polymers. The anhydrous form is widely used in fine chemical synthesis. It is non-oxidizing, has a high thermal stability, and is resistance to both oxidation and reduction, which makes it one of the more useful compounds in the super acids class. In the pharma industry, it is used to make a number of drug classes, including nucleosides, antibiotics, steroids, proteins and glycosides. Triflic anhydride reacts readily with water and has an unfavorable toxicity profile.

8.7 Preparation: Yellow-brown liquid. The boiling point is 167~170 ℃.The refractive index is 1.331.The relative density is 1.708.It is the strongest organic acids, easily soluble in water.Use carbon disulfide as raw material, with the reaction of iodine pentafluoride to produce trifluoromethyl disulfide.(CF3S) 2Hg was obtained when reacting with mercury; Then through oxidation of hydrogen oxide, trifluoromethanesulfonic acid is acquired.

8.8 Uses

It is used for organic synthesis, widely used in pharmaceutical and chemical industries, such as nucleosides, antibiotics, steroids, protein, sugar, vitamins synthesis, silicone rubber modification.
Isomerization and alkylation of the catalyst, the preparation of 2, 3-dihydro-2-indanone, tetralone, glycosides in the removal of glycoproteins.

8.9 Reactions: Trifluoromethanesulfonic acid acts as a catalyst for esterification reactions and an acidic titrant in nonaqueous acid-base titration. It is useful in protonations due to the presence of conjugate base triflate is non nucleophilic. It serves as a deglycosylation agent for glycoproteins. In addition, it is a precursor and a catalyst in organic chemistry. It reacts with acyl halides to prepare mixed triflate anhydrides, which are strong acylating agents used in Friedel-Crafts reactions. It acts as a key starting material for the preparation of ethers and olefins by reacting with alcohols as well as to prepare trifluoromethanesulfonic anhydride by dehydration reaction.

Catalyst used in the production 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.

8.10 Chemical Properties: Clear very light yellow liquid

8.11 Uses: Acid catalyst for the industry, Intermediate for liquid crystals, Pharmaceuticals intermediates, Intermediate for organic synthesis. One of the strongest available monoprotic acids.

8.12 Uses: As a catalyst in Friedel-Crafts type acylation, alkylation and polymerization reactions; as a solvent for ESR; as a nonaqueous strong acid titrant; with trifluoroacetic acid, q.v., in solid-phase peptide synthesis.

8.13 Definition: ChEBI: A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.

8.14 Safety Profile: A corrosive irritant to the skin, eyes, and mucous membranes. A strong acid. Violent reaction with acyl chlorides or aromatic hydrocarbons evolves toxic hydrogen chloride gas. When heated to decomposition it emits toxic fumes of Fand SOx. See also FLUORIDES.

8.15 Usage: Trifluoromethanesulfonic acid acts as a catalyst for esterification reactions and an acidic titrant in nonaqueous acid-base titration. It is useful in protonations due to the presence of conjugate base triflate is non nucleophilic. It serves as a deglycosylation agent for glycoproteins. In addition, it is a precursor and a catalyst in organic chemistry. It reacts with acyl halides to prepare mixed triflate anhydrides, which are strong acylating agents used in Friedel-Crafts reactions. It acts as a key starting material for the preparation of ethers and olefins by reacting with alcohols as well as to prepare trifluoromethanesulfonic anhydride by dehydration reaction.

8.16 Usage: As a catalyst for isomerization and alkylation

9. Computational chemical data

Molecular Weight: 150.07705g/mol
Molecular Formula: CHF₃O₃S
Compound Is Canonicalized: True
XLogP3-AA: 0.3
Exact Mass: 149.95984955
Monoisotopic Mass: 149.95984955
Complexity: 158
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 62.8
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcQAAMYBAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAQQACAAAAAAAABAAAAAAAIIAAAAAAHAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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