99727-20-5

Basic information

• Product Name: 1,1,1-TRIFLUORO-2-PHENYL-3-BUTYN-2-OL
• Synonyms: ALPHA-ETHYNYL-ALPHA-TRIFLUOROMETHYLBENZYL ALCOHOL;2-PHENYL-1,1,1-TRIFLUOROBUT-3-YN-2-OL;1,1,1-TRIFLUORO-2-PHENYL-3-BUTYN-2-OL;1,1,1-Trifluoro-2-phenyl-3-butyn-2-ol,95%;1,1,1-Trifluoro-2-phenyl-3-butyn-2-olalpha-Ethynyl-alpha-trifluoromethylbenzyl alcohol
• CAS NO: 99727-20-5
• Molecular Formula: C₁₀H₇F₃O
• Molecular Weight: 200.16
• Product Categories: Alkynes;Organic Building Blocks;Terminal
• Mol File: 99727-20-5.mol

Chemical Properties

• Boiling Point: 202.1 °C(lit.)
• Flash Point: 199 °F
• Appearance: /
• Density: 1.301 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0425mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• PKA: 9.95±0.10(Predicted)
• CAS DataBase Reference: 1,1,1-TRIFLUORO-2-PHENYL-3-BUTYN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-TRIFLUORO-2-PHENYL-3-BUTYN-2-OL(99727-20-5)
• EPA Substance Registry System: 1,1,1-TRIFLUORO-2-PHENYL-3-BUTYN-2-OL(99727-20-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 99727-20-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H7F3O/c1-2-9(14,10(11,12)13)8-6-4-3-5-7-8/h1,3-7,14H/t9-/m0/s1

Upstream product

• 434-45-7 2,2,2-Trifluoroacetophenone 
• 1066-26-8 sodium acetylide 
• 141946-97-6 (R,S)-1,1,1-trifluoro-2-phenylbut-3-yn-2-yl acetate 
• 141946-97-6 (+)-1,1,1-trifluoro-2-phenylbut-3-yn-2-yl acetate 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 134391-61-0 (E)-1,1,1,5,5,5-hexafluoro-2-phenylpent-3-en-2-ol 
• 1606139-27-8 C₁₉H₁₆F₃NO₃S 
• 1446099-85-9 (E)-4-(dimethyl(phenyl)silyl)-1,1,1-trifluoro-2-phenylbut-3-en-2-ol 
• 180619-98-1 [RhCl(P(CH(CH₃)2)3)2(CH₂CCC(C₆H₅)(CF₃))] 
• 180620-06-8 [RhCl(P(CH(CH₃)2)3)2(CH₂CC(C₆H₅)(CF₃))] 
• 1019336-22-1 C₂₅H₁₈F₃N₃O 
• 1019337-90-6 C₂₄H₁₆F₃N₃O 
• 1019337-32-6 C₂₅H₁₈F₃N₃O 
• 1019337-01-9 C₂₆H₁₇F₃N₄O 
• 1019336-44-7 C₂₆H₂₀F₃N₃O₂ 
• 141946-97-6 (R,S)-1,1,1-trifluoro-2-phenylbut-3-yn-2-yl acetate 
• 17257-71-5 (S)-Mosher acid 

Relevant articles and documents

Dynamic kinetic resolution of a tertiary alcohol

In spite of the tremendous success of dynamic kinetic resolutions for a broad range of compound classes, tertiary alcohols and their corresponding esters have still remained as one of the most challenging substrates for this type of process. This is due t

Catalytic Synthesis of Trifluoromethylated Allenes, Indenes, Chromenes, and Olefins from Propargylic Alcohols in HFIP

A general method to access CF3-substituted allenes from propargylic alcohols under Lewis acid catalysis in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvent is described. By tuning the reaction time and temperature, the obtained allenes rearr

Transition-Metal-Free Radical Hydrotrifluoromethylation of Alkynes

A combination of readily available and bench-stable CF3SO2Na and tBuOOH was efficiently used for hydrotrifluoromethylation of alkynes. An excellent trans-selectivity was demonstrated in the synthesis of alkenes. The developed mild reaction conditions allow the supression of the competing Meyer–Schuster-type rearrangement.

Palladium-Catalyzed Carboamination of Allylic Alcohols Using a Trifluoroacetaldehyde-Derived Tether

The selective palladium-catalyzed carboamination of allylic alcohols is reported on the basis of the use of an easily introduced trifluoroacetaldehyde-derived tether. Aminoalkynylation reactions were realized using alkynyl bromides and commercially available phosphine ligands. For aminoarylations, a new biaryl phosphine ligand, "Fu-XPhos", was introduced to overcome a competitive Heck pathway. The carboamination products were obtained in high yields and diastereoselectivity. The tether could be easily removed to give value-added amino alcohol building blocks.

Construction of Chiral Tri- and Tetra-Arylmethanes Bearing Quaternary Carbon Centers: Copper-Catalyzed Enantioselective Propargylation of Indoles with Propargylic Esters

Copper-catalyzed enantioselective propargylation of indoles with propargylic esters and sequential Huisgen cycloaddition with azides lead to the construction of chiral triarylmethanes, bearing a quaternary carbon center, with high to excellent enantioselectivities. The result described herein can be used in the enantioselective preparation of a tetraarylmethane.

Synthesis of Trifluoromethyl-allenes by Gold-Catalyzed Rearrangement of Propargyl Benzyl Ethers

A new method for the synthesis of trifluoromethyl-allenes from easily accessible α-trifluoromethyl-propargyl benzyl ether derivatives following a gold-catalyzed intramolecular hydride transfer has been developed. Various di- and trisubstituted trifluoromethyl-allenes were obtained in good to excellent yields.

One-Pot Three-Component Synthesis of Vicinal Diamines via In Situ Aminal Formation and Carboamination

A synthesis of vicinal diamines via in situ aminal formation and carboamination of allyl amines is reported. Employing highly electron-poor trifluoromethyl aldimines in their stable hemiaminal form was key to enable both a fast and complete aminal formation as well as the palladium-catalyzed carboamination step. The conditions developed allow the introduction of a wide variety of alkynyl, vinyl, aryl, and hetereoaryl groups with complete regioselectivity and high diastereoselectivity. The reaction exhibits a high functional-group tolerance. Importantly, either nitrogen atom of the imidazolidine products can be selectively deprotected, while removal of the aminal tether can be achieved in a single step under mild conditions to reveal the free diamine. We expect that this work will promote the further use of mixed aminal tethers in organic synthesis.

Kinetic resolution of esters from secondary and tertiary benzylic propargylic alcohols by an improved esterase-variant from Bacillus sp. BP-7

We described in a recent work the rational improvement of an esterase from Bacillus sp. BP7 aimed at investigating the efficiency of several esterase variants for enantiomeric resolution of acetate esters of tertiary alcohols. Variant EstBP7-AGA, bearing two aminoacidic changes in the oxyanion hole, showed an excellent E?>?100 enantioselectivity value towards a complex tertiary alcohol acetate (2-(4-pyridyl)-3-butyn-2-yl acetate) at low reaction temperature (4?°C). We here go further in the investigation of such esterase variant by analyzing the kinetic resolution of benzylic propargylic esters to prove that this enzyme is a powerful tool to obtain enantiomerically pure tertiary as well as secondary alcohols, provided that the structural integrity of the parent benzylic propargylic ester is maintained. Understanding the mode of action and interaction of such esterase variant with the assayed substrates will allow production of interesting pharmaceutical building blocks.

Platinum catalysed hydrosilylation of propargylic alcohols

A facile and user-friendly protocol has been developed for the selective synthesis of E-vinyl silanes derived from propargylic alcohols using a PtCl 2/XPhos catalyst system. The reaction is generally high yielding and provides a single regioiso

Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis

A gene coding for an esterase (EstEH112) was isolated from metagenome originated from Korean intertidal flat sediment. The putative esterase gene encoded a 340 amino acids protein with characteristic residues of lipolytic enzymes such as a conserved pentapeptide (GXSXG), the typical catalytic S-D-H triad, and a GGG(A)X-motif in the oxyanion hole near the active site similar to the hormone sensitive lipase (HSL) family. p-Nitrophenyl butyrate was the best substrate for the enzyme among the other p-nitrophenyl esters investigated. The apparent optimal temperature and pH for EstEH112 was 35°C and at pH 8.0, respectively. EstEH112 efficiently catalyzed the hydrolysis of various large tertiary alcohol esters. These characteristics of EstEH112 make it a potential candidate for application in biocatalysis.