4-(TRIFLUOROMETHYL)CYCLOHEXANOL Chemical Properties

Boiling point:

78 °C

Density 

1.23

refractive index 

1.4070 to 1.4110

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

pka

14.88±0.40(Predicted)

color 

Colorless to Almost colorless

Water Solubility 

Sparingly soluble in water.(0.26 g/L) (25°C),

InChI

InChI=1S/C7H11F3O/c8-7(9,10)5-1-3-6(11)4-2-5/h5-6,11H,1-4H2

InChIKey

VJUJYNJEPPWWHS-UHFFFAOYSA-N

SMILES

C1(O)CCC(C(F)(F)F)CC1

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36

RIDADR 

1993

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2906190090

4-(TRIFLUOROMETHYL)CYCLOHEXANOL Usage And Synthesis

Uses

It is used as pharmaceutical intermediate. Benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor.

Synthesis

Step A: Synthesis of 4-(trifluoromethyl)cyclohexanol; 4-hydroxytrifluorotoluene (5 g, 30.8 mmol) was placed in a high-pressure hydrogenation reactor, dissolved in acetic acid (15 ml) and platinum oxide (PtO, 500 mg) was added as a catalyst. The reactor was pressurized using hydrogen (50 psi) and the reaction was carried out at room temperature for 16 hours. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad to remove the catalyst, and the pH was adjusted by adding 1N sodium hydroxide solution to the filtrate, followed by extraction with diethyl ether. The organic phase was dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure at room temperature to afford the target product 4-(trifluoromethyl)cyclohexanol (4.5 g, 87% yield). Mass spectrometry analysis showed [M + H]+ peak of 169, corresponding to the molecular ion peak (M + 1).

References

[1] Patent: WO2008/7930, 2008, A1. Location in patent: Page/Page column 27
[2] , 1970, vol. 6, # 10, p. 2063 - 2067
[3] Zhurnal Organicheskoi Khimii, 1970, vol. 6, # 10, p. 2055 - 2060

4-(TRIFLUOROMETHYL)CYCLOHEXANOL(30129-18-1)Related Product Information

• Cyclohexanamine, 3-(trifluoromethyl)-
• 4-(Trifluoromethyl)cyclohexanecarboxylic acid
• 4-(TRIFLUOROMETHYL)CYCLOHEXANONE
• CIS-4-(TRIFLUOROMETHYL)CYCLOHEXANECARBOXYLIC ACID
• 3-(trifluoromethyl)cyclohexane-1-carboxylic acid
• 2-(trifluoromethyl)cyclohexane-1-carboxylic acid
• 4-(TRIFLUOROMETHYL)CYCLOHEXANAMINE
• 3-(TRIFLUOROMETHYL)CYCLOHEXANOL
• 4-(TRIFLUOROMETHYL)CYCLOHEXANOL
• METHYLCYCLOHEXANOL
• trans-4-(Trifluoromethyl)cyclohexanol
• cis-4-(Trifluoromethyl)cyclohexanol
• 2-(TRIFLUOROMETHYL)CYCLOHEXANOL
• 3,5-BIS(TRIFLUOROMETHYL)CYCLOHEXANOL
• 1-(Trifluoromethyl)cyclohexanol
• 2-(2-METHOXYETHOXY)-5-(TRIFLUOROMETHYL)CYCLOHEXANAMINE
• 2-PROPOXY-5-(TRIFLUOROMETHYL)CYCLOHEXANAMINE
• 2-(2,2,2-TRIFLUOROETHOXY)-5-(TRIFLUOROMETHYL)CYCLOHEXANAMINE