2-(Trifluoromethyl)phenothiazine Chemical Properties

Melting point:

188-190 °C(lit.)

Boiling point:

361.1±42.0 °C(Predicted)

Density 

1.3491 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

-2.60±0.20(Predicted)

form 

Solid

color 

Pale Yellow to Light Green

BRN 

226580

InChI

InChI=1S/C13H8F3NS/c14-13(15,16)8-5-6-12-10(7-8)17-9-3-1-2-4-11(9)18-12/h1-7,17H

InChIKey

RKGYJVASTMCSHZ-UHFFFAOYSA-N

SMILES

C1=C2C(SC3=C(N2)C=CC=C3)=CC=C1C(F)(F)F

CAS DataBase Reference

92-30-8(CAS DataBase Reference)

NIST Chemistry Reference

10H-phenothiazine, 2-(trifluoromethyl)-(92-30-8)

EPA Substance Registry System

10H-Phenothiazine, 2-(trifluoromethyl)- (92-30-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-22

Safety Statements 

36-37/39-26

WGK Germany 

3

RTECS 

SP5620000

Hazard Note 

Irritant

TSCA 

T

HS Code 

29349990

MSDS

• Language:English Provider:2-(Trifluoromethyl)phenothiazine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-(Trifluoromethyl)phenothiazine Usage And Synthesis

Chemical Properties

YELLOW TO GREEN POWDER

Uses

2-(Trifluoromethyl)phenothiazine is used in the synthesis of antitubercolosis pharmaceuticals as well as antiproliferatives.

Definition

ChEBI: 2-(trifluoromethyl)-10H-phenothiazine is a member of phenothiazines.

Synthesis

GENERAL STEPS: To an oven-dried 25 mL milled-neck test tube fitted with a stirrer, S-(2-acetamidophenyl) thioacetate (0.5 mmol), 3-iodo-4-chlorobenzotrifluoride (0.6 mmol), Cs2CO3 (2.0 mmol), and DMF (3 mL) were added sequentially. The test tube was sealed with a rubber septum, evacuated and replaced with argon for three cycles. The reaction mixture was stirred at 130 °C for 10 hours. Upon completion of the reaction, it was cooled to room temperature, the reaction was quenched with deionized water (20 mL) and extracted with ethyl acetate (20 mL x 3). The organic phases were combined, dried with anhydrous MgSO4 and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography using gradient elution (eluent: petroleum ether/ethyl acetate) to afford the target compound 2-trifluoromethyl phenothiazine.

References

[1] Synthetic Communications, 2017, vol. 47, # 7, p. 710 - 715

2-(Trifluoromethyl)phenothiazine(92-30-8)Related Product Information

• (Trifluoromethyl)trimethylsilane
• Phenothiazine
• 3-Trifluoromethylphenol
• Trifluoromethanesulfonic acid
• Trifluoromethanesulfonic anhydride
• 4-Bromobenzotrifluoride
• 4-(Trifluoromethyl)benzaldehyde
• 3-（trifluoromethyl) Cinnamaldehyde
• 3-(Trifluoromethyl)benzaldehyde
• FLUPHENAZINE HYDROCHLORIDE
• 10-(3-(4-Methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)phenothiazine
• Oxaflumazine
• 10-(3-(2-Hydroxyethyl)piperazinopropyl)-2-(trifluoromethyl)phenothiazine
• Fluphenazine decanoate
• Ciclofenazine
• Flutiazin
• 10-[3-(4-METHYL-1-PIPERAZINYL)PROPYL]-2-TRIFLUOROMETHYL-PHENOTHIAZINE DIHYDROCHLORIDE
• triflupromazine