3-(3-(Trifluoromethyl)phenyl)propan-1-ol Chemical Properties

Boiling point:

68-71℃/0.4mm

Density 

1.10

refractive index 

1.4620 to 1.4660

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

15.04±0.10(Predicted)

form 

Liquid

color 

Colorless

InChI

InChI=1S/C10H11F3O/c11-10(12,13)9-5-1-3-8(7-9)4-2-6-14/h1,3,5,7,14H,2,4,6H2

InChIKey

QWXKQVIMGVVIBX-UHFFFAOYSA-N

SMILES

C1(CCCO)=CC=CC(C(F)(F)F)=C1

Safety Information

HS Code 

2906290090

3-(3-(Trifluoromethyl)phenyl)propan-1-ol Usage And Synthesis

Chemical Properties

Brown Oil

Uses

3-(Trifluoromethyl)benzenepropanol-d4 is an intermediate in the synthesis of Cinacalcet-d4 Hydrochloride (C441803), a labeled analogue of Cinacalcet Hydrochloride (C441800), the (R) enantiomer of Cinacalcet which is used in clinical trial in secondary hyperparathyroidism.

Definition

ChEBI: 3-[3-(trifluoromethyl)phenyl]propan-1-ol is an organofluorine compound that is 3-phenylpropan-1-ol bearing a trifluoromethyl group at position 3 on the phenyl ring. It is an organofluorine compound and a member of propan-1-ols.

Synthesis

To a solution of 14.5 g (72.5 mmol) of purified 3-(3-trifluoromethylphenyl)propargyl alcohol in 50 mL of 2-propanol was added 0.38 g of 10% Pd/C (Selcat Q6). The reaction mixture was subjected to hydrogenation at a temperature of 42-45°C and a pressure of 5 bar until all feedstocks were completely converted (about 5 hours). Upon completion of the reaction, it was filtered to remove the catalyst and the catalyst was washed with a small amount of 2-propanol. Subsequently, the filtrate was concentrated by evaporation under reduced pressure. The crude product obtained (14.5 g, 100.0%) was purified by distillation under reduced pressure, resulting in 10.5 g (yield: 72.1%) of the target product 3-(3-trifluoromethylphenyl)propanol as an almost colorless oil (boiling point: 58-60 °C/1.1-1.5 mbar).

References

[1] Organic Letters, 2019, vol. 21, # 1, p. 65 - 69
[2] Patent: US2010/267988, 2010, A1. Location in patent: Page/Page column 4
[3] Patent: EP2327684, 2011, A1. Location in patent: Page/Page column 6
[4] Patent: US2011/124917, 2011, A1. Location in patent: Page/Page column 3

3-(3-(Trifluoromethyl)phenyl)propan-1-ol(78573-45-2)Related Product Information

• 3-(3-Trifluoromethylphenyl)propionic acid
• 3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONALDEHYDE
• Cinacalcet Impurity B
• 4-(TRIFLUOROMETHYL)HYDROCINNAMIC ACID
• Cinacalcet Impurity 38 HCl
• (E)-m-(trifluoromethyl)cinnamic acid
• 1-NAPHTHALEN-2-YL-ETHYLAMINE
• Cinacalcet IMpurity 7
• (R)-1-(Naphthalen-2-yl)ethanamine hydrochloride
• (1R)-1-(5-methylnaphthalen-1-yl)ethan-1-amine
• Cinacalcet IMpurity 3
• Cinacalcet Impurity 46
• 3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL
• Methanesulfonic acid 3-(3-trifluoroMethylphenyl)propyl ester
• cinacalcet iMpurity 4
• N-(1-(naphthalen-1-yl)ethyl)forMaMide
• Cinacalcet impurity C
• Cinacalcet Impurity 45