(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol

Base Information

• Chemical Name: (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
• CAS No.: 127852-28-2
• Molecular Formula: C₁₀H₈F₆O
• Molecular Weight: 258.163
• Hs Code.: 29062990
• European Community (EC) Number: 603-245-7
• UNII: 26EP435WQ9
• DSSTox Substance ID: DTXSID80381243
• Nikkaji Number: J1.427.078G
• Wikidata: Q72447321
• Mol file: 127852-28-2.mol

Synonyms:127852-28-2;(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol;(r)-1-(3,5-bis(trifluoromethyl)phenyl)ethanol;(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethanol;(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethanol;(r)-1-[3,5-bis(trifluoromethyl)phenyl]ethan-1-ol;(r)-1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol;(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethan-1-ol;MFCD03093010;Benzenemethanol, alpha-methyl-3,5-bis(trifluoromethyl)-, (alphaR)-;(R)-1-(3,5-Bis-trifluoromethylphenyl)ethanol;SCHEMBL265045;AMY369;DTXSID80381243;26EP435WQ9;BCP27255;CS-D0702;AKOS005063416;AKOS010366354;AC-6709;AS-19515;(1R)-3,5-bis(trifluoromethyl)phenylethanol;B4131;(r)-[3,5-bis(trifluoromethyl)phenyl] ethanol;(r)-1-[3,5-bis(trifluoromethyl)-phenyl]ethanol;(r)-1-[bis-3,5-(trifluoromethyl)phenyl]ethanol;EN300-1268241;(r)-1-[3,5-bis(trifluoro-methyl)-phenyl]ethanol;AS-813/43495601;1-[3,5-Bis(trifluoromethyl)phenyl]ethanol, (R)-;J-502134;(+)-(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol;(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethyl Alcohol;benzenemethanol, alpha-methyl-3,5-bis(trifluoromethyl);(R)-3,5-Bis(trifluoromethyl)-alpha-methylbenzyl Alcohol;(alphaR)-alpha-Methyl-3,5-bis(trifluoromethyl)benzenemethanol;benzenemethanol, a-methyl-3,5-bis(trifluoromethyl)-, (ar)-;(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol, >=98.0% (GC);alpha-Methyl-3,5-bis(trifluoromethyl)benzenemethanol, (alphaR)-

Chemical Property of (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol

Chemical Property:

• 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
• Storage Temp.: -20°C Freezer
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 258.04793385
• Heavy Atom Count: 17
• Complexity: 237

Purity/Quality:

99% ^*data from raw suppliers

(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-52/53-22
• Safety Statements: 26-36/37/39-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O
• Isomeric SMILES: C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O
• Uses: (R)-[3,5-bis (trifluoromethyl) phenyl] ethanol is an important chiral intermediate for the synthesis of novel chemotherapeutic and antiemetic drugs NK-1 receptor antagonists. Antidepressants have good potential efficacy in treating a range of central and peripheral nervous system depressions. (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol is an intermediate in the synthesis of Aprepitant (A729800), a novel selective neurokinin-1 (NK-1) receptor antagonist. In vitro studies using human liver microsomes indicate that Aprepitant is metabolised primarily by CYP3A4 with minor metabolism by CYP1A2 and CYP2C19, and no metabolism by CYP2D6, CYP2C9, or CYP2E1. Antiemetic.

Technology Process of (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol

There total 30 articles about (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3,5-bis(trifluoromethyl)phenyl methyl ketone (30071-93-3) → (R)-[3,5-bis(trifluoromethyl)phenyl]ethanol (368-63-8,68120-60-5,127852-28-2)

Guidance literature:

With C₅₁H₅₇ClFeN₂OP₂⁽¹⁺⁾*BF₄^(1-); potassium tert-butylate; isopropyl alcohol; at 28 ℃; for 0.00277778h; Reagent/catalyst; enantioselective reaction; Catalytic behavior;

DOI:10.1126/science.1244466

Reference yield: 99.8%

3,5-bis(trifluoromethyl)phenyl methyl ketone (30071-93-3) → (S)-3,5-bis(trifluoromethyl)-1-phenylethanol (225920-05-8) + (R)-[3,5-bis(trifluoromethyl)phenyl]ethanol (368-63-8,68120-60-5,127852-28-2)

Guidance literature:

With C₄₃H₅₆FeN₃P₂⁽¹⁺⁾*BF₄^(1-); sodium triethylborohydride; In tetrahydrofuran; toluene; at 50 ℃; for 0.5h; Reagent/catalyst; Time; Catalytic behavior; Glovebox;

DOI:10.1021/jacs.8b12506

Reference yield: 99.2%

(R)-O-acetyl-1-(3,5-bis(trifluoromethyl)phenyl)ethanol (534613-13-3) → (R)-[3,5-bis(trifluoromethyl)phenyl]ethanol (368-63-8,68120-60-5,127852-28-2)

Guidance literature:

With lithium hydroxide; In methanol; for 10h; Reflux;

upstream raw materials:

3,5-bis(trifluoromethyl)phenylmagnesium bromide

acetaldehyde

3,5-bis(trifluoromethyl)phenyl methyl ketone

(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl-2,2,2-trichloroethanimidoate

Downstream raw materials:

3,5-bis(trifluoromethyl)phenyl methyl ketone

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

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

(R)-1-(1-(bromomethoxy)ethyl)-3,5-bis(trifluoromethyl)benzene

Refernces

• 1、 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. "A convergent approach to the synthesis of aprepitant: a potent human NK-1 receptor antagonist". . p. 8001 - 8004. Retrieved 2007.
• 2、 Kurbanoglu, Esabi B.,Zilbeyaz, Kani,Taskin, Mesut,Kurbanoglu, Namudar I.. "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". . p. 2759 - 2763. Retrieved 2009.
• 3、 Gelo-Pujic, Mirjana,Le Guyader, Frederic,Schlama, Thierry. "Microbial and homogenous asymmetric catalysis in the reduction of 1-[3,5-bis(trifluoromethyl)phenyl]ethanone". . p. 2000 - 2005. Retrieved 2006.
• 4、 Hansen, Karl B.,Chilenski, Jennifer R.,Desmond, Richard,Devine, Paul N.,Grabowski, Edward J. J.,Heid, Richard,Kubryk, Michele,Mathre, David J.,Varsolona, Richard. "Scalable, efficient process for the synthesis of (R)-3,5- bistrifluoromethylphenyl ethanol via catalytic asymmetric transfer hydrogenation and isolation as a DABCO inclusion complex". . p. 3581 - 3587. Retrieved 2003.
• 5、 Khiar, Noureddine,Leal, Manuel Pernia,Navas, Raquel,Moya, Juan Francisco,Perez, Maria Victoria Garcia,Fernandez, Inmaculada. "P/S ligands derived from carbohydrates in Rh-catalyzed hydrosilylation of ketones". . p. 355 - 360. Retrieved 2012.
• 6、 Wang, Nengqiang,Huang, Jin,Luo, Hongdou,Wang, Pu,Li, Jun. "Purification and characterization of a new carbonyl reductase from Leifsonia xyli HS0904 involved in stereoselective reduction of 3,5-bis(trifluoromethyl) acetophenone". . p. 1 - 6. Retrieved 2013.
• 7、 Demmans, Karl Z.,Seo, Chris S. G.,Lough, Alan J.,Morris, Robert H.. "From imine to amine: An unexpected left turn.: Cis -β Iron(II) PNNP′ precatalysts for the asymmetric transfer hydrogenation of acetophenone". . p. 6531 - 6541. Retrieved 2017.
• 8、 Xu, Tingting,Wang, Can,Zhu, Shaozhou,Zheng, Guojun. "Enzymatic preparation of optically pure t-butyl 6-chloro-(3R,5S)-dihydroxyhexanoate by a novel alcohol dehydrogenase discovered from Klebsiella oxytoca". . p. 72 - 79. Retrieved 2017.
• 9、 Hess, Reto,Vargas, Angelo,Mallat, Tamas,Buergi, Thomas,Baiker, Alfons. "Inversion of enantioselectivity in the platinum-catalyzed hydrogenation of substituted acetophenones". . p. 117 - 128. Retrieved 2004.
• 10、 Topf, Christoph,Vielhaber, Thomas. "Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol". . . Retrieved 2021/07/10.