145412-54-0

Basic information

• Product Name: DICYCLOHEXYL(TRIFLUOROMETHANESULFONYLOXY)BORANE
• Synonyms: TRIFLUOROMETHANESULFONIC ACID DICYCLOHEXYLBORYL ESTER;DICYCLOHEXYL(TRIFLUOROMETHANESULFONYLOXY)BORANE;DICYCLOHEXYLBORON TRIFLATE;Dicyclohexylborontrifluoromethanesulfonate;Dicyclohexylboron Triflate Trifluoromethanesulfonic Acid Dicyclohexylboryl Ester;Dicyclohexyl{[(trifluoromethyl)sulphonyl]oxy}borane;Dicyclohexylboranyl trifluoromethanesulphonate, Dicyclohexylboranyl triflate;Dicyclohexylboron trifluoromethanesulfonate 97%
• CAS NO: 145412-54-0
• Molecular Formula: C₁₃H₂₂BF₃O₃S
• Molecular Weight: 326.18
• Product Categories: B (Classes of Boron Compounds);Borinic Acids
• Mol File: 145412-54-0.mol

Chemical Properties

• Melting Point: 59-65°C
• Boiling Point: 337.874°C at 760 mmHg
• Flash Point: 158.141°C
• Appearance: /
• Density: 1.207g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.449
• Storage Temp.: Refrigerator
• CAS DataBase Reference: DICYCLOHEXYL(TRIFLUOROMETHANESULFONYLOXY)BORANE(CAS DataBase Reference)
• NIST Chemistry Reference: DICYCLOHEXYL(TRIFLUOROMETHANESULFONYLOXY)BORANE(145412-54-0)
• EPA Substance Registry System: DICYCLOHEXYL(TRIFLUOROMETHANESULFONYLOXY)BORANE(145412-54-0)

Safety Data

• Hazard Codes: C
• Statements: 34-22
• Safety Statements: 36/37/39-45-26
• RIDADR: 1760
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 145412-54-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Dicyclohexyl(trifluoromethanesulfonyloxy)borane is used as a reducing agent for the conversion of aldehydes, ketones, and imines to their corresponding alcohols or amines. Its mild and selective nature makes it suitable for delicate organic synthesis processes where other reducing agents might be too harsh or non-selective.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, DCTB is utilized as a reagent in the synthesis of various organic compounds, including those that have medicinal properties. Its high reactivity and selectivity are crucial for the production of complex molecules that are often required in the development of new drugs.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical sector, DCTB is employed for the synthesis of organic compounds that are used in the development of pesticides, herbicides, and other agricultural chemicals. Its ability to selectively reduce certain functional groups without affecting others is particularly beneficial in creating specific agrochemical products.
Used in Laboratory Research:
Dicyclohexyl(trifluoromethanesulfonyloxy)borane is also used in academic and industrial research laboratories for the preparation of complex organic molecules. Its versatility as a reagent allows researchers to explore new synthetic pathways and develop novel compounds for various applications.

InChI:InChI=1/C13H22BF3O3S/c15-13(16,17)21(18,19)20-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 1088-01-3 tricyclohexylborane 
• 13292-87-0 dimethylsulfide borane complex 
• 110-83-8 cyclohexene 
• 1568-65-6 bis(cyclohexanyl)borane 

Downstream Products

• 467213-73-6 dicyclohexylboranyl-acetic acid 2,6-diisopropyl-phenyl ester 

Relevant articles and documents

Asymmetric Total Synthesis of (?)-Dehydrocostus Lactone by Domino Metathesis

An efficient total synthesis of the sesquiterpenoid (?)-dehydrocostus lactone is reported. Our earlier approach by a domino enediyne metathesis was extended by a domino dienyne metathesis strategy to give access to suitably functionalized hydroazulene cores. Highly stereoselective asymmetric anti aldol reactions provided the enantiopure substrates for this key step of our synthesis. Multiple hydroboration/oxidation of the resulting hydroazulenes set up three out of four stereogenic centers in a single step. First, oxidation to give a diketo-γ-lactone enabled an enantioselective formal synthesis of the target guaianolide. Subsequently, the final steps of this approach were improved by using a double carbonyl olefination at the stage of a masked γ-butyrolactone, which completed the synthesis in a much more efficient way.

Temperature-and Reagent-Controlled Complementary Syn-and Anti-Selective Enolboration-Aldolization of Substituted Phenylacetates

In contrast to methyl phenylacetates, methyl arylacetates do not provide syn-aldols in the dicyclohexylboron triflate/triethylamine (Chx2BOTf/Et3N)-mediated enolboration-aldolization reaction. However, a combination of a less bulky boron reagent (dibutylboron triflate, n-Bu2BOTf), a bulky amine (i-Pr2NEt), and ambient temperature is required to obtain syn-aldols from methyl arylacetates. The corresponding anti-aldol products have been synthesized by the enolboration-aldolization of methyl arylacetates in the presence of Chx2BOTf/Et3N at a lower temperature. We report the first example of a complementary syn-and anti-selective enolboration-aldolization of arylacetates.

Enantioselective Total Synthesis of the Guaianolide (-)-Dehydrocostus Lactone by Enediyne Metathesis

The hydroazulene core of the bioactive sesquiterpenoid (-)-dehydrocostus lactone was generated by domino enediyne metathesis. A triple hydroboration/oxidation of the resultant conjugated triene installed three out of four stereogenic centers of the target in a single step. The enantiopure acyclic metathesis substrate was readily available by an asymmetric anti aldol reaction. Masking of the O-lactone as an acetal allowed for an efficient completion of the synthesis through late-stage double carbonyl olefination.

Synthesis of a diastereomer of the marine macrolide lytophilippine A

The synthesis of a diastereomer of lytophilippine A required 22 longest linear steps using known building blocks. Cross-metathesis/asymmetric aldol addition and regioselective esterification/ring-closing metathesis served as efficient combi tools for scaffold construction. Detailed NMR investigations in different solvent (systems) provide evidence for a deep-seated configurational misassignment of the molecule named lytophilippine A.

Directed hydrogenations and an Ireland-Claisen rearrangement linked to Evans-Tishchenko chemistry: The highly efficient total synthesis of the marine cyclodepsipeptide doliculide

Two new convergent total syntheses have been developed for the cytotoxic, actin microfilament-stabilizing marine cyclodepsipeptide doliculide (1). A key strategic element of both routes is the establishment of the central stereogenic center of the characteristic polydeoxypropionate stereotriad by means of a hydroxyl-directed catalytic hydrogenation of a trisubstituted double bond. The requisite olefin substrates were obtained through a modified Suzuki-Miyaura coupling or through Ireland-Claisen rearrangement of a propionate ester, respectively; the latter was the direct result of a highly selective Evans-Tishchenko reduction of a hydroxy ketone that had been obtained in a stereoselective Paterson aldol reaction. Doliculide (1) was finally obtained in a total number of 17 or 15 (14) linear steps, respectively, which represents a substantial improvement over previous syntheses of this highly bioactive natural product.

Solvent- or temperature-controlled diastereoselective aldol reaction of methyl phenylacetate

Unlike the enolboration-aldolization of methyl propanoate, the choice of either the solvent or temperature determines the diastereoselectivity during the enolboration-aldolization of methyl phenylacetate. In CH2Cl 2, the reaction favors the anti-pathway at -78 °C and the syn-pathway at rt. Conversely, the reaction produces the anti-isomer up to rt and the syn-isomer at refluxing temperatures in nonpolar solvents.

Boron-mediated aldol reaction of carboxylic esters: Complementary anti- and syn-selective asymmetric aldol reactions

The boron-mediated aldol reaction of carboxylic esters is described in detail. Contrary to the general belief that carboxylic esters are inert under the condition of the boron enolate formation, propionate esters are enolized with certain combinations of a boron triflate and an amine. More importantly, the stereochemical course of the aldol reaction can be controlled by the judicious selection of the enolization reagents. Treatment of propionate esters with c-Hex2BOTf and triethylamine produces anti-aldol products, and that with Bu2BOTf and diisopropylethylamine gives syn-aldol products selectively after reaction with aldehydes. Complementary anti- and syn-selective asymmetric aldol reactions with structurally related, readily available chiral norephedrine-derived propionate esters are developed.

A practical synthesis of the lipophilic side chain of the polyoxypeptins

The lipophilic side chain of the cyclic depsipeptide polyoxypeptin A (1) and B (2), strong apoptosis inducers, has been synthesised as an ester of mixed methyl ketal 18. The key step is an asymmetric anti-aldol reaction of the designed 2-(N-2-methylbenzyl