36967-85-8

Basic information

• Product Name: Benzoic acid (trifluoromethanesulfonic acid)anhydride
• Synonyms: Benzoic acid (trifluoromethanesulfonic acid)anhydride;Benzoyl=trifluoromethanesulfonate;Trifluoromethanesulfonic Acid Benzoyl Ester Benzoyl Triflate
• CAS NO: 36967-85-8
• Molecular Formula: C₈H₅F₃O₄S
• Molecular Weight: 254.18
• Mol File: 36967-85-8.mol

Chemical Properties

• Boiling Point: 94°C/2.2mmHg(lit.)
• Flash Point: 114°C
• Appearance: /
• Density: 1.542±0.06 g/cm3(Predicted)
• Storage Temp.: <0°C
• CAS DataBase Reference: Benzoic acid (trifluoromethanesulfonic acid)anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid (trifluoromethanesulfonic acid)anhydride(36967-85-8)
• EPA Substance Registry System: Benzoic acid (trifluoromethanesulfonic acid)anhydride(36967-85-8)

Safety Data

• Hazardous Substances Data: 36967-85-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Benzoic acid (trifluoromethanesulfonic acid) anhydride is used as an acylating agent for the conversion of alcohols, amines, and phenols into their corresponding acylated products. Its high reactivity allows for efficient and selective acylation reactions, making it a valuable tool in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzoic acid (trifluoromethanesulfonic acid) anhydride is employed as a reagent for the synthesis of drug molecules. Its ability to acylate functional groups in organic compounds enables the creation of new pharmaceutical agents with desired properties.
Used in Catalyst Applications:
Benzoic acid (trifluoromethanesulfonic acid) anhydride is also used as a catalyst in a variety of chemical reactions. Its catalytic properties can enhance the rate and selectivity of certain reactions, facilitating the production of desired products in the chemical and materials industries.
Safety Precautions:
Due to its high reactivity and corrosive nature, Benzoic acid (trifluoromethanesulfonic acid) anhydride should be handled with care by trained professionals. It should be used in a well-ventilated area to minimize exposure risks and potential hazards.

Upstream product

• 2923-28-6 silver trifluoromethanesulfonate 
• 65-85-0 benzoic acid 
• 1493-13-6 trifluorormethanesulfonic acid 
• 532-32-1 sodium benzoate 
• 98-88-4 benzoyl chloride 

Downstream Products

• 37854-29-8 cis-1,2-Dibenzoyloxycyclohexane 
• 16611-67-9 (2,5-dichlorophenyl)(phenyl)methanone 
• 106016-58-4 10-(benzoyloxy)-9-phenanthrenediazonium trifluoromethanesulfonate 
• 4044-60-4 2,5-dimethylbenzophenone 
• 38584-43-9 adamantan-1-yl benzoate 
• 4147-13-1 estra-1,3,5(10)-triene-3,17β-diol dibenzoate 
• 50-50-0 Estradiol 3-benzoate 
• 110977-42-9 1-hydroxybicyclo<2.2.2>oct-2-yl benzoate 
• 110977-38-3 2-benzoyloxybicyclo<2.2.2>oct-1-yl triflate 
• 110977-40-7 1-hydroxybicyclo<3.2.2>non-2-yl benzoate 
• 110977-39-4 1-hydroxy-2-adamantyl benzoate 
• 142888-94-6 1-Iodo-2-adamantyl benzoatee 
• 160833-78-3 1-Fluoro-2-adamantyl benzoate 
• 160833-75-0 1-Chloro-2-adamantyl benzoate 

Relevant articles and documents

Decarboxylation with Carbon Monoxide: The Direct Conversion of Carboxylic Acids into Potent Acid Triflate Electrophiles

We report a new strategy for the conversion of carboxylic acids into potent acid triflate electrophiles. The reaction involves oxidative carbonylation of carboxylic acids with I2 in the presence of AgOTf, and is postulated to proceed via acyl hypoiodites that react with CO to form acid triflates. Coupling this chemistry with subsequent trapping with arenes offers a mild, room temperature approach to generate ketones directly from broadly available carboxylic acids without the use of corrosive and reactive Lewis or Bronsted acid additives, and instead from compounds that are readily available, stable, and functional group compatible.

Asymmetric synthesis of complicated bicyclic and tricyclic polypropanoates via the double Diels-Alder addition of 2,2′-ethylidenebis[3,5-dimethylfuran]

A new, non-iterative method for the asymmetric synthesis of long-chain and polycyclic polypropanoate fragments starting from 2,2′-ethylidenebis[3,5-dimethylfuran] (2) has been developed. Diethyl (2E,5E)-4-oxohepra-2,5-dienoate (6) added to 2 to give a single meso-adduct 7 containing nine stereogenic centers. Its desymmetrization was realized by hydroboration with (+)-IpcBH2 (isopinocampheylborane), leading to diethyl (1S,2R,3S,4S,4aS,7R,8R,8aR,9aS,10R,10aR)-1,3,4,7,8,8a,9,9a-octahydro-3 -hydroxy-2,4,5,7,10-pentamethyl-9-oxo-2H-10H-2.4a:7.10a-diepoxyanthracene -1,8-dicarboxylate ((+)-8: 78% e.e.). Alternatively, 7 was converted to meso-(1R,2R,4R,4aR,5S,7S,8S,8aR,9aS,10s,10aS)-1,8-bis(acetoxymethyl) -1,8,8a,9a-tetrahydro-2,4,5,7,10-pentamethyl-2H-10H-2.4a:7.10a -diepoxyanthracene-3,6,9(4H,5H,7H)-trione (32) that was reduced enantioselectively by BH3 catalyzed by methyloxazaborolidine 19 derived from L-diphenylprolinol giving (1S,2S,4S,4aS,5S,6R,7R,8R,8aS,9aR,10R,10aS)-1,8-bis(acetoxymethyl) -1,8,8a,9a-tretrahydro-6-hydroxy-2,4,5,7,10-pentamethyl-2H,10H-2.4a:7.10a -diepoxyanthracene-3,9(4H,7H)-dione ((-)-33: 90% e.e.). Chemistry was explored to carry out chemoselective 7-oxabicyclo[2,2,1]heptanone oxa-ring openings and intra-ring C-C bond cleavage. Polycyclic polypropanoates such as (1R,2S,3R,4R,4aR,5S,6R,7S,8R,9R,10R,11S,12aR)-1-(ethoxycarbonyl) -1,3,4,7,9,10,11,12,12a-decahydro-3,11-dihydroxy-2,4,5,7,9-pentamethyl-12 -oxo-2H,5H-2,4a:6,9:6,11-triepoxybenzocyclodecene-10,8-carbolactone (51). (1S,2R,3R,4R,4aS,5S,7S,8R,9R,10R,12S,12aS)-1,10-bis(acetoxymethyl) tetradecahydro-8-(methoxymethoxy)-2,4,5,7,9-pentamethyl-3,9-bis ([2-(trimethylsilyl)ethoxy]methoxy)-6,11-epoxycyclodecene-4a,6,11,12-tetrol ((+)-83), and (1R,2R,3R,4aR,4bR,5S,6R,7R,8R,8aS,9S,10aR)-3,5-bis(acetoxymethyl) -4a,8a-dihydroxy-1-(methoxymethoxy)-2,6,8,9,10a-pentamethyl-2,7-bis ([2-(trimethysilsyl)ethoxy]methoxy)dodecahydrophenanthrene-4,10-dione (85) were obtained in few synthetic steps.

Benzoyl Trifluoromethanesulfonate. A Mild Reagent for the Benzoylation of Sterically Hindered Hydroxyls

Benzoyl trifluoromethanesulfonate (BzOTf) is a highly efficient reagent for the benzoylation of a variety of alcohols under mild conditions.These include hindered secondary and tertiary hydroxyls, phenols, and α-glycols.Sensitive functionality is stable when the reaction is performed in the presence of pyridine.Several unique rearrangements of Lewis acidsensitive compounds were also effected.

Carboxylic Trifluoromethanesulfonic and Methanesulfonic Anhydrides, Synthesis and Dissociation Tendency

Carbonyl chlorides 1 react with silver trifluoromethanesulfonate (2) and silver methanesulfonate (6) to give carboxylic trifluoromethanesulfonic anhydrides 3 and carboxylic methanesulfonic anhydrides 7, resp., in good yields; the anhydrides 3 may be synth

The Synthesis and Some Reactions of N-Methylnitrilium Trifluoromethanesulphonate Salts

N-Methylnitrilium trifluoromethanesulphonate (triflate) salts, prepared from nitriles and methyl triflate, have been shown to be useful reagents for the synthesis of aromatic ketimines and ketones, amidinium, imidate, and thioimidate salts, benzimidazoles, benzoxazoles, benzothiazoles, quinazolinones, and 1,2,4-triazolinium salts.