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
• Article Data: 9

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

General Description

Dicyclohexyl(trifluoromethanesulfonyloxy)borane, also known as DCTB, is a boron-based chemical compound commonly used in synthetic organic chemistry as a mild and selective reducing agent. It is a colorless, air-sensitive liquid with a characteristic pungent odor. DCTB is often employed in the reduction of aldehydes, ketones, and imines to their corresponding alcohols or amines, respectively. It is also used in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals. DCTB is considered a versatile and efficient reagent in organic synthesis due to its high reactivity and selectivity, making it an important tool for the preparation of complex molecules in the laboratory.

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

Downstream Products

• 944943-14-0 (1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6S,8S)-3-hydroxy-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate 
• 944943-15-1 (1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6R,8S)-3-hydroxy-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate 
• 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.

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.

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.