3',5'-Bis(trifluoromethyl)acetophenone Chemical Properties

Boiling point:

95-98 °C (15 mmHg)

Density 

1.422 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4221(lit.)

Flash point:

180 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow

Specific Gravity

1.422

BRN 

2384789

InChI

InChI=1S/C10H6F6O/c1-5(17)6-2-7(9(11,12)13)4-8(3-6)10(14,15)16/h2-4H,1H3

InChIKey

MCYCSIKSZLARBD-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)C

CAS DataBase Reference

30071-93-3(CAS DataBase Reference)

NIST Chemistry Reference

3',5'-Bis(trifluoromethyl)acetophenone(30071-93-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39-36

RIDADR 

3439

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29147000

MSDS

• Language:English Provider:3',5'-Bis(trifluoromethyl)acetophenone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3',5'-Bis(trifluoromethyl)acetophenone Usage And Synthesis

Uses

3',5'-Bis(Trifluoromethyl)acetophenone is a reactant that has been used in the preparation of pyrazole carboxamide derivatives with antibacterial and antifungal activity.

Chemical Properties

CLEAR PALE YELLOW LIQUID

Uses

3'',5''-Bis(Trifluoromethyl)acetophenone is a reactant that has been used in the preparation of pyrazole carboxamide derivatives with antibacterial and antifungal activity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 68, p. 3695, 2003 DOI: 10.1021/jo026903n

Synthesis

General procedure for the synthesis of 3,5-bis(trifluoromethyl)acetophenone from (R)-1-[3,5-bis(trifluoromethyl)-phenyl]ethanol: BTC (0.41 g, 1.39 mmol) was dissolved in anhydrous dichloromethane (5 mL) under the protection of nitrogen and cooled to -15 °C in an ice-salt bath. At this temperature, a solution of (R)-1-[3,5-bis(trifluoromethyl)-phenyl]ethanol (1.24 g, 4.17 mmol) in anhydrous dichloromethane (5 mL) was slowly added dropwise for 0.5 hours. After continued stirring for 0.5 h, an anhydrous dichloromethane (5 mL) solution of benzyl alcohol (0.3 g, 2.78 mmol) was added dropwise for 0.5 h at the same temperature. After stirring for 0.5 h, triethylamine (0.84 g, 8.34 mmol) was slowly added while making sure that the reaction temperature was kept below -15 °C. Upon completion of the reaction, 10% aqueous hydrochloric acid was added dropwise under ice bath conditions until the pH of the reaction mixture reached 2. The organic layer was separated by extracting the mixture with hexane or petroleum ether (10 mL x 2). After concentration of the organic layer, it was purified by fast chromatography (silica gel; hexane) to afford the target product 3,5-bis(trifluoromethyl)acetophenone (0.27 g, 92% yield). The aqueous layer can be used to recover by-product V and excess (R)-1-[3,5-bis(trifluoromethyl)-phenyl]ethanol.

References

[1] Synthetic Communications, 2016, vol. 46, # 10, p. 885 - 892
[2] Patent: WO2004/94358, 2004, A1. Location in patent: Page 4-5
[3] Patent: WO2004/94358, 2004, A1. Location in patent: Page 5
[4] European Journal of Organic Chemistry, 2018, vol. 2018, # 23, p. 3031 - 3035

3',5'-Bis(trifluoromethyl)acetophenone(30071-93-3)Related Product Information

• Chalcone
• 4-Fluoroacetophenone
• Acetophenone
• 4'-Methylacetophenone
• 3'-Methylacetophenone
• Trifluoroacetophenone
• 2-(Trifluoromethyl)benzoic acid
• 3-(Trifluoromethyl)benzaldehyde
• Trifluoromethanesulfonic acid
• 2-Aminobenzotrifluoride
• 4'-(Trifluoromethyl)acetophenone
• 3',5'-BIS(TRIFLUOROMETHYL)-2-BROMOACETOPHENONE
• ETHYL 3-[3,5-DI(TRIFLUOROMETHYL)PHENYL]-3-OXOPROPANOATE
• 2-[3,5-BIS(TRIFLUOROMETHYL)BENZOYL]BENZOIC ACID
• 3,5-BIS(TRIFLUOROMETHYL)BENZOPHENONE
• 3,3',5,5'-TETRAKIS(TRIFLUOROMETHYL)BENZOPHENONE
• 3',5'-BIS(TRIFLUOROMETHYL)PROPIOPHENONE
• Trifluoromethyl