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127852-28-2

  • Product Name:(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
  • Molecular Formula:C10H8F6O
  • Molecular Weight:258.163
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Product Details

pd_meltingpoint:53-58℃

Purity:99%

(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol 127852-28-2 Powder In Medicine with Global USP Fast Delivery

  • Molecular Formula:C10H8F6O
  • Molecular Weight:258.163
  • Vapor Pressure:0.746mmHg at 25°C 
  • Melting Point:53-58℃ 
  • Refractive Index:1.418 
  • Boiling Point:175.8 °C at 760 mmHg 
  • PKA:13.99±0.20(Predicted) 
  • Flash Point:60.1 °C 
  • PSA：20.23000 
  • Density:1.376 g/cm3 
  • LogP:3.77750 

(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol(Cas 127852-28-2) Usage

Preparation

At present, the methods for preparing optically pure (R)-[3,5-bis (trifluoromethyl) phenyl] ethanol include chemical methods and biological methods. Chemical synthesis requires the use of expensive transition metal Ru and other chemical catalysts, complicated steps, harsh reaction conditions, high energy consumption, large pollution, and low yield. Biological law is the use of free enzymes or whole cells for catalytic preparation. It has the characteristics of mild reaction conditions, high catalytic efficiency, and strong specificity.

General Description

(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol is a key intermediate for the synthesis of aprepitant, a potent human neurokinin-1 (NK-1) receptor.

InChI:InChI=1/C10H8F6O/c1-5(17)6-2-7(9(11,12)13)4-8(3-6)10(14,15)16/h2-5,17H,1H3

127852-28-2 Relevant articles

Asymmetric Hydrogenation of 3,5-Bistrifluoromethyl Acetophenone in Pilot Scale with Industrially Viable Ru/Diphosphine-Benzimidazole Complexes

Xu, Liang,Huang, Zhi-Hong,Sandoval, Christian A.,Gu, Lian-Quan,Huang, Zhi-Shu

, p. 1137 - 1141 (2014)

A novel efficient asymmetric hydrogenati...

A convergent approach to the synthesis of aprepitant: a potent human NK-1 receptor antagonist

Elati, Chandrashekar R.,Kolla, Naveenkumar,Gangula, Srinivas,Naredla, Anitha,Vankawala, Pravinchandra J.,Avinigiri, Muttu L.,Chalamala, Subrahmanyeswararao,Sundaram, Venkatraman,Mathad, Vijayavitthal T.,Bhattacharya, Apurba,Bandichhor, Rakeshwar

, p. 8001 - 8004 (2007)

A simple and convergent approach to enan...

Efficient synthesis of (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol, a key intermediate for aprepitant, an NK-1 receptor antagonist

Vankawala, Pravinchandra J.,Kolla, Naveenkumar,Elati, Chandrashekar R.,Sreenivasulu,Kumar, K. Arun,Anjaneyulu, Yerrimilli,Venkatraman, Sundaram,Bhattacharya, Apurba,Mathad, Vijayavitthal T.

, p. 3439 - 3446 (2007)

Enzyme-catalyzed efficient synthesis of ...

Total production of (R)-3,5-bistrifluoromethylphenyl ethanol by asymmetric reduction of 3,5-bis(trifluoromethyl)-acetophenone in the submerged culture of Penicillium expansum isolate

Kurbanoglu, Esabi B.,Zilbeyaz, Kani,Taskin, Mesut,Kurbanoglu, Namudar I.

, p. 2759 - 2763 (2009)

A total of 82 fungal isolates were scree...

Bioreduction of 3,5-bis(trifluoromethyl)acetophenone using ionic liquid as a co-solvent catalyzed by recombinant Escherichia coli cells

Wang, Nengqiang,Li, Jun,Sun, Jing,Huang, Jin,Wang, Pu

, p. 119 - 125 (2015)

We investigated the asymmetric bioreduct...

Microbial and homogenous asymmetric catalysis in the reduction of 1-[3,5-bis(trifluoromethyl)phenyl]ethanone

Gelo-Pujic, Mirjana,Le Guyader, Frederic,Schlama, Thierry

, p. 2000 - 2005 (2006)

Two complementary approaches for the ena...

Identification of ketone reductase ChKRED20 from the genome of Chryseobacterium sp. CA49 for highly efficient anti-Prelog reduction of 3,5-bis(trifluoromethyl)acetophenone

Liu, Yan,Tang, Tuo-Xian,Pei, Xiao-Qiong,Zhang, Chao,Wu, Zhong-Liu

, p. 1 - 8 (2014)

A strain of Chryseobacterium sp. CA49 wa...

Scalable, efficient process for the synthesis of (R)-3,5- bistrifluoromethylphenyl ethanol via catalytic asymmetric transfer hydrogenation and isolation as a DABCO inclusion complex

Hansen, Karl B.,Chilenski, Jennifer R.,Desmond, Richard,Devine, Paul N.,Grabowski, Edward J. J.,Heid, Richard,Kubryk, Michele,Mathre, David J.,Varsolona, Richard

, p. 3581 - 3587 (2003)

(R)-3,5-Bistrifluoromethylphenyl ethanol...

Effective synthesis of (S)-3,5-bistrifluoromethylphenyl ethanol by asymmetric enzymatic reduction

Pollard, David,Truppo, Matthew,Pollard, Jennifer,Chen, Cheng-yi,Moore, Jeffrey

, p. 554 - 559 (2006)

The synthesis of (S)-3,5-bistrifluoromet...

P/S ligands derived from carbohydrates in Rh-catalyzed hydrosilylation of ketones

Khiar, Noureddine,Leal, Manuel Pernia,Navas, Raquel,Moya, Juan Francisco,Perez, Maria Victoria Garcia,Fernandez, Inmaculada

, p. 355 - 360 (2012)

Reported is the synthesis of a number of...

Influence of cofactor regeneration strategies on preparative-scale, asymmetric carbonyl reductions by engineered escherichia coli

Dascier, Dimitri,Kambourakis, Spiros,Hua, Ling,David Rozzell,Stewart, Jon D.

, p. 793 - 800 (2014)

This study was designed to determine whe...

Purification and characterization of a new carbonyl reductase from Leifsonia xyli HS0904 involved in stereoselective reduction of 3,5-bis(trifluoromethyl) acetophenone

Wang, Nengqiang,Huang, Jin,Luo, Hongdou,Wang, Pu,Li, Jun

, p. 1 - 6 (2013)

Leifsonia xyli HS0904 can stereoselectiv...

High-yielding metalloenzymatic dynamic kinetic resolution of fluorinated aryl alcohols

Bogár, Krisztián,B?ckvall, Jan-E.

, p. 5471 - 5474 (2007)

Dynamic kinetic resolution (DKR) of vari...

From imine to amine: An unexpected left turn.: Cis -β Iron(II) PNNP′ precatalysts for the asymmetric transfer hydrogenation of acetophenone

Demmans, Karl Z.,Seo, Chris S. G.,Lough, Alan J.,Morris, Robert H.

, p. 6531 - 6541 (2017)

A novel PNN ligand bearing an orthopheny...

Half-sandwich ruthenium catalyst bearing an enantiopure primary amine tethered to an N-heterocyclic carbene for ketone hydrogenation

Wan, Kai Y.,Sung, Molly M. H.,Lough, Alan J.,Morris, Robert H.

, p. 6827 - 6842 (2017)

By using a copper transmetalation reagen...

Enzymatic preparation of optically pure t-butyl 6-chloro-(3R,5S)-dihydroxyhexanoate by a novel alcohol dehydrogenase discovered from Klebsiella oxytoca

Xu, Tingting,Wang, Can,Zhu, Shaozhou,Zheng, Guojun

, p. 72 - 79 (2017)

Alcohol dehydrogenases can catalyze the ...

Enantioselective ketone hydrogenation: From R&D to pilot scale with industrially viable Ru/phosphine-oxazoline complexes

Naud, Frederic,Spindler, Felix,Rueggeberg, Carsten J.,Schmidt, Andreas T.,Blaser, Hans-Ulrich

, p. 519 - 523 (2007)

The development of a pilot process for t...

Inversion of enantioselectivity in the platinum-catalyzed hydrogenation of substituted acetophenones

Hess, Reto,Vargas, Angelo,Mallat, Tamas,Buergi, Thomas,Baiker, Alfons

, p. 117 - 128 (2004)

The enantioselective hydrogenation of ri...

Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity

Du, Tian,Wang, Biwen,Wang, Chao,Xiao, Jianliang,Tang, Weijun

supporting information, p. 1241 - 1244 (2020/10/02)

A chiral cobalt pincer complex, when com...

A Cobalt(II) Complex Bearing the Amine(imine)diphosphine PN(H)NP Ligand for Asymmetric Transfer Hydrogenation of Ketones

Huo, Shangfei,Chen, Hong,Zuo, Weiwei

supporting information, p. 37 - 42 (2020/10/21)

Novel chiral cobalt complex a containing...

Effectiveness and Mechanism of the Ene(amido) Group in Activating Iron for the Catalytic Asymmetric Transfer Hydrogenation of Ketones

Xue, Qingquan,Wu, Rongliang,Wang, Di,Zhu, Meifang,Zuo, Weiwei

supporting information, p. 134 - 147 (2021/02/05)

I-interacting ligands of the diphosphino...

Mechanochemical, Water-Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst

Kolcsár, Vanessza Judit,Sz?ll?si, Gy?rgy

, (2022/01/04)

Asymmetric catalytic reactions are among...

127852-28-2 Process route

vinyl acetate
108-05-4,9003-20-7

vinyl acetate

1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol
68120-60-5,127852-28-2,368-63-8

1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol

(R)-O-acetyl-1-(3,5-bis(trifluoromethyl)phenyl)ethanol
534613-13-3

(R)-O-acetyl-1-(3,5-bis(trifluoromethyl)phenyl)ethanol

(S)-3,5-bis(trifluoromethyl)-1-phenylethanol
225920-05-8

(S)-3,5-bis(trifluoromethyl)-1-phenylethanol

(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol
368-63-8,68120-60-5,127852-28-2

(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol

Conditions
Conditions Yield
With Novozyme-435 lipase; In tetrahydrofuran; at 20 ℃; for 72h; Resolution of racemate; Enzymatic reaction;
40%
89 % ee
Candida antartica lipase B; In various solvent(s); at 40 ℃; for 2h; under 67505.4 Torr;
 
Isopropenyl acetate
108-22-5

Isopropenyl acetate

1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol
68120-60-5,127852-28-2,368-63-8

1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol

(R)-O-acetyl-1-(3,5-bis(trifluoromethyl)phenyl)ethanol
534613-13-3

(R)-O-acetyl-1-(3,5-bis(trifluoromethyl)phenyl)ethanol

(S)-3,5-bis(trifluoromethyl)-1-phenylethanol
225920-05-8

(S)-3,5-bis(trifluoromethyl)-1-phenylethanol

(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol
368-63-8,68120-60-5,127852-28-2

(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol

Conditions
Conditions Yield
With Novozyme-435 lipase; In tetrahydrofuran; at 20 ℃; for 72h; Resolution of racemate; Enzymatic reaction;
38%
86 % ee

127852-28-2 Upstream products

  • 30071-93-3
    30071-93-3

    3,5-bis(trifluoromethyl)phenyl methyl ketone

  • 112981-69-8
    112981-69-8

    3,5-bis(trifluoromethyl)phenylmagnesium bromide

  • 75-07-0
    75-07-0

    acetaldehyde

  • 68120-60-5
    68120-60-5

    1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol

127852-28-2 Downstream products

  • 349-59-7
    349-59-7

    3,5-bis(trifluoromethyl)styrene

  • 30071-93-3
    30071-93-3

    3,5-bis(trifluoromethyl)phenyl methyl ketone

  • 225920-05-8
    225920-05-8

    (S)-3,5-bis(trifluoromethyl)-1-phenylethanol

  • 368-63-8
    368-63-8

    (R)-[3,5-bis(trifluoromethyl)phenyl]ethanol

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