ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Quinoline compounds 2,8-Bis(trifluoromethyl)-4-quinolinol

2,8-Bis(trifluoromethyl)-4-quinolinol

Product Name2,8-Bis(trifluoromethyl)-4-quinolinol
CAS35853-41-9
MFC11H5F6NO
MW281.15
EINECS252-762-0
MOL File35853-41-9.mol

Chemical Properties

Melting point	130-134 °C(lit.)
Boiling point	305.9±37.0 °C(Predicted)
Density	1.4837 (estimate)
storage temp.	Inert atmosphere,Room Temperature
form	Liquid
pka	5.84±0.40(Predicted)
color	Clear colorless to slightly yellow
InChI	InChI=1S/C11H5F6NO/c12-10(13,14)6-3-1-2-5-7(19)4-8(11(15,16)17)18-9(5)6/h1-4H,(H,18,19)
InChIKey	JIWHKBAFGFPZKM-UHFFFAOYSA-N
SMILES	N1C2C(=CC=CC=2C(F)(F)F)C(O)=CC=1C(F)(F)F
CAS DataBase Reference	35853-41-9(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
RIDADR	2811
WGK Germany	3
HazardClass	IRRITANT
HS Code	29334900

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

light grey powder

Uses

2,8-Bis(trifluoromethyl)-4-quinolinol is a simplified quinine derivative that exhibits the highest antifungal activity among its series and serves as a lead compound for further structural modification[6]. This compound acts as a starting material for synthesizing quinoline derivatives with various substitutions at the 4-OH position, including specific series such as compounds 4g–i[7-8]. It reacts with methyl chloroacetate in DMF using K2CO3 to form intermediates, and undergoes conversion to yield 4-bromo-2,8-bis(trifluoromethyl)quinoline[6].

Synthesis

372-31-6

88-17-5

35853-41-9

2-(Trifluoromethyl)aniline (0.54 mL, 4.3 mmol) and ethyl 4,4,4-trifluoro-3-oxobutanoate (0.62 mL, 4.3 mmol) were mixed in a round-bottomed flask fitted with a large oval stir bar. Subsequently, polyphosphoric acid (4.0 g) was added to the reaction system. The reaction mixture was stirred at 120 °C for 3 h under nitrogen protection. Upon completion of the reaction, the reaction was quenched with ice water (50 mL) to give a golden-brown sticky substance. Extraction was carried out with dichloromethane (2 x 20 mL) and the organic layers were combined and dried over anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure to give a beige solid product that did not require further purification (0.27 g, 23% yield).

References

[1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 8, p. 3374 - 3383
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2012, vol. 51, # 9, p. 1411 - 1416,6
[3] Monatshefte fur Chemie, 2008, vol. 139, # 2, p. 179 - 181
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5466 - 5469
[5] CrystEngComm, 2018, vol. 20, # 16, p. 2316 - 2323
[6] Chen, Y.-J., Ma, K.-Y., Du, S.-S., Zhang, Z.-J., Wu, T.-L., Sun, Y., Liu, Y.-Q., Yin, X.-D., Zhou, R., Yan, Y.-F., Wang, R.-X., He, Y.-H., Chu, Q.-R., Tang, C. (2021). Antifungal Exploration of Quinoline Derivatives against Phytopathogenic Fungi Inspired by Quinine Alkaloids. Journal of Agricultural and Food Chemistry, 69(41), 12156–12170. https://doi.org/10.1021/acs.jafc.1c05677
[7] Qin, L.-L., Yang, L., Zhang, Z.-J., Zhang, L.-J., Zhang, W., Jin, Y.-R., Luo, X.-F., Li, F.-P., Zhang, S.-Y., Bian, Q., Mou, G.-L., Dai, T.-L., Ma, L., Liu, Y.-Q. (2024). Design, Synthesis, and Biological Evaluation of Novel Quinoline Derivatives against Phytopathogenic Bacteria Inspired from Natural Quinine Alkaloids. Journal of Agricultural and Food Chemistry. https://doi.org/10.1021/acs.jafc.4c05509
[8] Bhagat, S., Arfeen, M., Das, G., Ramkumar, M., Khan, S. I., Tekwani, B. L., Bharatam, P. V. (2019). Design, synthesis and biological evaluation of 4-aminoquinoline-guanylthiourea derivatives as antimalarial agents. Bioorganic Chemistry, 91, 103094. https://doi.org/10.1016/j.bioorg.2019.103094

2,8-Bis(trifluoromethyl)-4-quinolinol

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