(S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol Chemical Properties

Melting point:

53.0 to 57.0 °C

Boiling point:

175.8±35.0 °C(Predicted)

Density 

1.376±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

13.99±0.20(Predicted)

color 

White to Off-White

λmax

254nm(lit.)

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/t5-/s3

InChIKey

MMSCIQKQJVBPIR-GQMHJJTINA-N

SMILES

C1(C(F)(F)F)C=C(C=C(C(F)(F)F)C=1)[C@@H](O)C |&1:14,r|

CAS DataBase Reference

225920-05-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

Hazard Note 

Irritant

HS Code 

29062990

(S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol Usage And Synthesis

Chemical Properties

White solid

Uses

Aprepitant intermediate.

Synthesis

General procedure: under argon protection, the ruthenium complex Ru(OTf)[(S,S)-iso-BuSO2dpen] (p-cymene) (1.4 mg, 0.002 mmol), potassium formate (1.0 g, 12 mmol), and 3,5-bis(trifluoromethyl)acetophenone (2.56 g, 10 mmol, substrate to catalyst ratio 5000:1) were added to a 20 mL glass Schlenk reaction tube. Subsequently, methanol (6 mL) was added and the reaction was stirred at 50 °C for 24 hours. Upon completion of the reaction, (S)-1-[3,5-bis(trifluoromethyl)phenyl]ethanol was obtained in 100% yield with an enantiomeric excess (ee) value of 87.7%.

References

[1] Patent: US2011/282077, 2011, A1. Location in patent: Page/Page column 8
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7329 - 7332
[3] Tetrahedron Asymmetry, 2006, vol. 17, # 4, p. 554 - 559
[4] Patent: CN108059579, 2018, A. Location in patent: Paragraph 0057-0061
[5] Tetrahedron, 2004, vol. 60, # 3, p. 789 - 797

(S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol(225920-05-8)Related Product Information

• PHENYL VALERATE
• Methyltriphenylphosphonium bromide
• 2,2,2-TRIFLUOROETHANOL-D3
• Trimethylphenylammonium chloride
• N-Methyldiethanolamine
• Ethyl acetate
• Chlorodimethylphenylsilane
• Phenethyl alcohol
• 2-Methylaminoethanol
• PHENYL RESIN
• 3,3',5,5'-TETRAKIS(TRIFLUOROMETHYL)BENZHYDROL
• 2-[3,5-Bis(trifluoromethyl)phenyl]propan-2-ol
• Phenylacetic acid
• (1R)-1-[3,7-BIS(TRIFLUOROMETHYL)PHENYL]ETHANOL,1-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]ETHANOL
• (R)-1-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]ETHANOL,(1R)-1-[3,6-BIS(TRIFLUOROMETHYL)PHENYL]ETHANOL
• (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine
• (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether
• 2-(3,5-bis(trifluoromethyl)phenyl)ethanol