340-05-6

Basic information

• Product Name: 1-PHENYL-2,2,2-TRIFLUOROETHANOL
• Synonyms: (±)α-(trifluoromethyl)benzylalcohol;(R,S)-2,2,2-Trifluoro-1-phenyl-ethanol;1-Phenyl-2,2,2-trifluorethanol;Benzenemethanol,α-(trifluoromethyl)-,(±)-;α-(Trifluoromethyl)benzylalcohol;(+/-)-ALPHA-(TRIFLUOROMETHYL)BENZYLALCOHOL;ALPHA-(TRIFLUOROMETHYL)BENZYL ALCOHOL;2,2,2-TRIFLUORO-1-PHENYLETHANOL
• CAS NO: 340-05-6
• Molecular Formula: C₈H₇F₃O
• Molecular Weight: 176.14
• EINECS: 206-429-1
• Product Categories: Benzene series
• Mol File: 340-05-6.mol

Chemical Properties

• Melting Point: 74.3-75.2 °C
• Boiling Point: 64-65 °C5 mm Hg(lit.)
• Flash Point: 184 °F
• Appearance: /liquid
• Density: 1.297 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.462
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.91±0.10(Predicted)
• BRN: 3197623
• CAS DataBase Reference: 1-PHENYL-2,2,2-TRIFLUOROETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-2,2,2-TRIFLUOROETHANOL(340-05-6)
• EPA Substance Registry System: 1-PHENYL-2,2,2-TRIFLUOROETHANOL(340-05-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• HazardClass: IRRITANT
• Hazardous Substances Data: 340-05-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C8H7F3O/c9-8(10,11)7(12)6-4-2-1-3-5-6/h1-5,7,12H

Upstream product

• 434-45-7 2,2,2-Trifluoroacetophenone 
• 17750-24-2 1-propyl-1,4-dihydronicotinamide 
• 952-92-1 1-Benzyl-1,4-dihydronicotinamide 
• 287-92-3 Cyclopentane 
• 79048-93-4 5-Methyl-1-(2',6'-Dichlorobenzyl)-1,4-dihydronicotinamide 
• 91999-49-4 6-Methyl-1-(2',6'-Dichlorobenzyl)-1,4-dihydronicotinamide 
• 91999-48-3 2-Methyl-1-(2',6'-Dichlorobenzyl)-1,4-dihydronicotinamide 
• 13502-54-0 1-(2',6'-Dichlorobenzyl)-1,4-dihydronicotinamide 
• 124898-12-0 trimethyl[(2,2,2-trifluoro-1-phenylethoxy)]silane 
• 75-46-7 trifluoromethan 
• 99838-02-5 tetraoctylammonium (2-pyrrolidonide) 
• 100-52-7 benzaldehyde 
• 75-63-8 Bromotrifluoromethane 
• 2314-97-8 iodotrifluoromethane 

Downstream Products

• 573-78-4 phthalic acid mono-(2,2,2-trifluoro-1-phenyl-ethyl ester) 
• 384-65-6 1-chloro-2,2,2-trifluoroethylbenzene 
• 434-42-4 1,1,1-trifluoro-2-bromo-2-phenylethane 
• 17659-27-7 1-benzoyloxy-1-phenyl-2,2,2-trifluoroethane 
• 125888-88-2 Phosphorochloridic acid 2,2,2-trifluoro-ethyl ester 2,2,2-trifluoro-1-phenyl-ethyl ester 
• 100664-05-9 bis(2,2,2-trifluoroethyl) (α-trifluoromethylbenzyl) phosphate 
• 84877-46-3 2,2,2-trifluoro-1-phenylethyl trifluoromethanesulfonate 
• 93524-65-3 2-(2',5'-difluorophenyl)-1,1,1-trifluoro-2-phenylethane 
• 125888-91-7 Phosphorochloridic acid 2,2,3,3,4,4,5,5,5-nonafluoro-pentyl ester 2,2,2-trifluoro-1-phenyl-ethyl ester 
• 100664-09-3 Phosphoric acid bis-(2,2,3,3,4,4,4-heptafluoro-butyl) ester 2,2,2-trifluoro-1-phenyl-ethyl ester 
• 40121-55-9 1-phenyl-2,2,2-trifluoroethyl α-methoxy-α-(trifluoromethyl)phenylacetate 
• 128816-79-5 (2,2,2-trifluoroethyl)(2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptyl)(α-trifluoromethylbenzyl) phosphate 
• 135311-72-7 (S)-Cyano-fluoro-phenyl-acetic acid 2,2,2-trifluoro-1-phenyl-ethyl ester 
• 135311-72-7 1-phenyl-2,2,2-trifluoroethyl α-cyano-α-fluorophenylacetate 

Relevant articles and documents

Synthesis, Reactivity and Structural Properties of Trifluoromethylphosphoranides

Phosphoranides are interesting hypervalent species which serve as model compounds for intermediates or transition states in nucleophilic substitution reactions at trivalent phosphorus substrates. Herein, the syntheses and properties of stable trifluoromet

Homoleptic cobalt(II) phenoxyimine complexes for hydrosilylation of aldehydes and ketones without base activation of cobalt(II)

Air-stable, easy to prepare, homoleptic cobalt(II) complexes bearing pendant-modified phenoxyimine ligands were synthesized and determined. The complexes exhibited high catalytic performance for reducing aldehydes and ketones via catalytic hydrosilylation, where a hydrosilane and a catalytic amount of the cobalt(II) complex were added under base-free conditions. The reaction proceeded even in the presence of excess water, and excellent functional-group tolerance was observed. Subsequent hydrolysis gave the alcohol in high yields. Moreover, H2O had a critical role in activation of the Co(II) catalyst with hydrosilane. Several additional results also indicated that the cobalt(II) center acts as an active catalyst in the hydrosilylation of aldehydes and ketones.

Trifluoromethyl reagent as well as synthesis method and application thereof

The invention discloses a trifluoromethyl reagent as well as a synthesis method and application thereof, wherein the structural formula of the trifluoromethyl reagent is as shown in formula I in the specification. According to the invention, diphenyl trifluoromethylphosphine and iodomethane are used as raw materials, and are heated in an organic solvent to carry out an addition reaction to prepare the trifluoromethylation reagent. The method is simple and convenient in process, high in yield and capable of realizing 10-gram-level large-scale preparation; more importantly, the trifluoromethylation reagent can be used as a free radical and a nucleophilic reagent to be applied to free radical addition reaction and simple nucleophilic addition reaction to prepare different types of trifluoromethylation products, so that the method has important application value.

Formation of a hydride containing amido-zincate using pinacolborane

Amido-zincates containing hydrides are underexplored yet potentially useful complexes. Attempts to access this type of zincate through combining amido-organo zincates and pinacolborane (HBPin)viaZn-C/H-BPin exchange led instead to preferential formation of amide-BPin and/or [amide-BPin(Y)]?(Y = Ph, amide, H), when the amide is hexamethyldisilazide or 2,2,6,6-tetramethylpiperidide and the hydrocarbyl group was phenyl or ethyl. In contrast, the use of a dipyridylamide (dpa) based arylzinc complex led to Zn-C/H-BPin metathesis being the major outcome. Independent synthesis and full characterisation of two LnLi[(dpa)ZnPh2] (L = THF,n= 3; L = PMDETA,n= 1) complexes,1and3, respectively, enabled reactivity studies that demonstrated that these species display zincate type reactivity (by comparison to the lower reactivity of the neutral complex (Me-dpa)ZnPh2,4, Me-dpa = 2,2′-dipyridyl-N-methylamine). This included1performing the rapid deprotonation of 4-ethynyltoluene and also phenyl transfer to α,α,α-trifluoroacetophenone in contrast to neutral complex4. Complex1reacted with one equivalent of HBPin to give predominantly PhBPin (ca.90%) and a lithium amidophenylzincate containing a hydride unit, complex7-A, as the major zinc containing product. Complex7-Atransfers hydride to an electrophile preferentially over phenyl, indicating it reacts as a hydridozincate. Attempts to react1with >1 equivalent of HBPin or with catecholborane led to more complex outcomes, which included significant borane and dpaZn substituent scrambling, two examples of which were crystallographically characterised. While this work provides proof of principle for Zn-C/H-BPin exchange as a route to form an amido-zincate containing a hydride, amido-organozincates that undergo more selective Zn-C/H-BPin exchange still are required.

One-Pot Successive Turbo Grignard Reactions for the Facile Synthesis of α-Aryl-α-Trifluoromethyl Alcohols

A novel straightforward one-pot methodology for two successive turbo Grignard reagent (iPrMgCl·LiCl) reactions, was developed for a facile synthesis of α-aryl-α-trifluoromethyl alcohols, motifs of value in pharmaceutical chemistry. The method displayed broad functional group tolerance, including reducible groups. Dual roles of iPrMgCl·LiCl were exploited in the tandem reaction with commercially available iodoarenes or iodoheteroarenes and 2,2,2-trifluoroethyl trifluoroacetate. The process encompasses three successive reactions in a one-pot process: the iPrMgCl·LiCl-mediated iodine/magnesium-exchange reaction of iodoarenes or iodoheteroarenes; nucleophilic addition of various generated aryl or heteroarylmagnesium reagents to 2,2,2-trifluoroethyl trifluoroacetate; and the reduction of in-situ generated aryl trifluoromethyl ketones with iPrMgCl·LiCl, to produce the corresponding α-aryl or α-heteroaryl-α-trifluoromethyl alcohols bearing various substituents, including reducible functional groups in good to excellent yields.

Potassium Fluoride-Catalyzed Hydroboration of Aldehydes and Ketones: Facile Reduction to Primary and Secondary Alcohols

A catalytic hydroboration of various ketones and aldehydes can be achieved in the presence of inexpensive and commercially available inorganic salts containing fluoride anion. As a result, the reduction of carbonyl moieties to the corresponding primary and secondary alcohols can be achieved at room temperature under mild conditions.

Synthesis of Unsymmetric Triarylmethanes Bearing CF 3-Substituted All-Carbon Quaternary Stereocenters: 1,6-Arylation of δ-Trifluo romethyl Substituted para -Quinone Methides

Pre-synthesized δ-CF 3-δ-aryl-disubstituted para -quinone methides bearing δ-substituents were identified as isolable and storable substrates for 1,6-arylation reactions. A broad range of electron-rich arenes and heteroarenes participated in the arylation process, furnishing a wide array of unsymmetrical CF 3-substituted triarylmethanes in high efficiency. The mild and expeditious protocol exhibited broad scopes of both arene and para -quinone methide components.

Structural Elucidation of Silver(I) Amides and Their Application as Catalysts in the Hydrosilylation and Hydroboration of Carbonyls

This study details the isolation and characterisation of three novel silver(I) amides in solution and solid-state, [Ag(Cy3P)(HMDS)] 2, [Ag(Cy3P){N(TMS)(Dipp)}] 3 and [Ag(Cy3P)2(NPh2)] 4. Their catalytic abilities have proved successful in hydroboration and hydrosilylation reactions with a full investigation performed with complex 2. Both protocols proceed under mild conditions, displaying exceptional functional-group tolerance and chemoselectivity, in excellent conversions at competitive reaction times. This work reveals the first catalytic hydroboration of aldehydes and ketones performed by a silver(I) catalyst.

Gas/Liquid-Phase Micro-Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N-Sulfinylimines

A micro-flow nucleophilic trifluoromethylation of carbonyl compounds using gaseous fluoroform was developed. This method also allows the first micro-flow transformation of N-sulfinylimines into trifluoromethyl amines with excellent diastereoselectivity. To demonstrate the synthetic utility of this micro-flow synthesis, the formal micro-flow synthesis of Efavirenz is described.

Design of Manganese Phenol Pi-complexes as Shvo-type Catalysts for Transfer Hydrogenation of Ketones

Catalytic hydrogenation is one of the most important reactions both in academic research and industry. We explored ability of the manganese pi-complexes to act as Shvo-type catalysts for transfer hydrogenation of ketones. DFT calculations suggested that the transfer of hydrogen atoms from the hypothetical intermediate [(C6Me3H2OH)Mn(CO)2H] to acetone has low activation barrier of 10.9 kcal mol?1. Experimentally a number of ketones with various functional groups (OMe, NH2, Cl, CF3, pyridyl) were successfully reduced in isopropanol at 90 °C in the presence of the complex [(C6Me3H2OH)Mn(CO)3]BF4 (1 mol %) and tBuOK (75 mol %). However, further investigation revealed that the reduction was mainly promoted by base rather than the manganese complex.