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

Name
2,8-Bis(trifluoromethyl)-4-quinolinol
EINECS 252-762-0
CAS No. 35853-41-9
Article Data9
CAS DataBase
Density 1.506 g/cm³
Solubility
Melting Point 130-134 °C(lit.)
Formula C₁₁H₅F₆NO
Boiling Point 238 °C at 760 mmHg
Molecular Weight 281.157
Flash Point 97.8 °C
Transport Information
Appearance light grey powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2,8-Bis(Trifluoromethyl)-4-quinolinol;2,8-Bis(trifluoromethyl)-4-hydroxyquinoline;4-Hydroxy-2,8-bis(trifluoromethyl)quinoline;
PSA 33.12000
LogP 3.97800

Synthetic route

: 372-31-6
ethyl 4,4,4-trifluoroacetoacetate

: 88-17-5
2-(trifluoromethyl)benzenamine

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

Conditions

Conditions	Yield
With polyphosphoric acid at 150℃; for 3h;	91%
With polyphosphoric acid at 150℃;	77%
With polyphosphoric acid at 20 - 120℃; for 2h; Inert atmosphere;	75%

: mefloquine hydrochloride

A: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

B: 57120-56-6
2,8-bis(trifluoromethyl)-4-quinoline carboxaldehyde

C: 35853-50-0
2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid

D: 2-oxo-8-trifluoromethyl-1,2-dihydro-quinoline-4-carbaldehyde

Conditions

Conditions	Yield
With sodium hydroxide; potassium dihydrogenphosphate; oxygen In methanol; water for 0.583333h; pH=7.4; Kinetics; Quantum yield; Further Variations:; pH-values; Reagents; Solvents; O2 conc., ionic strength, buffer conc., addition of scavengers; Decomposition; Irradiation;

...Expand

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: C11H4(2)HF6NO

Conditions

Conditions	Yield
With water-d2; sulfuric acid-d2 In iso-butanol at 150 - 200℃; for 4h;	99%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 35853-45-3
(2,8-bis-trifluoromethyl)-4-bromoquinoline

Conditions

Conditions	Yield
With phosphorus(V) oxybromide	99%
With phosphorus(V) oxybromide at 120℃; for 5h; Inert atmosphere;	98%
With phosphorus(V) oxybromide at 140℃; Inert atmosphere;	98%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 83012-13-9
2,8-bis-(trifluoromethyl)-4-chloro-quinoline

Conditions

Conditions	Yield
With trichlorophosphate at 80℃; for 4h;	98%
With trichlorophosphate at 110℃; for 2h;	85%
With trichlorophosphate at 80℃; for 4h;	82%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 927-74-2
1-butyn-4-ol

: 1141427-66-8
2,5-bis(trifluoromethyl)-4-(3-butyn-1-yloxy)quinoline

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;	97%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 208465-72-9
methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate

: 1141427-88-4
2-[[[2,8-bis(trifluoromethyl)-4-quinolinyl]oxy]methyl]-4-oxazolecarboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 2,8-bis(trifluoromethyl)quinolin-4-ol With potassium carbonate In acetone for 0.25h; Reflux; Stage #2: methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate With potassium iodide In acetone for 2h; Williamson synthesis; Reflux;	97%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 98-59-9
p-toluenesulfonyl chloride

: 150785-70-9
2,8-bis(trifluoromethyl)quinolin-4-yl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 0℃; pH=11;	96%
With sodium hydroxide In water; acetone at 0℃; pH=11;	96%
With sodium hydroxide In acetone at 5℃; for 0.5h; pH=11;	91%
With sodium hydroxide In acetone at 10℃; for 1h; pH=7.5; Inert atmosphere;	91%

: 113647-42-0, 18668-72-9
3-Bromo-but-1-yne

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 1197932-33-4
4-(1-methylprop-2-ynyloxy)-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
Stage #1: 2,8-bis(trifluoromethyl)quinolin-4-ol With potassium carbonate In acetone for 0.5h; Reflux; Stage #2: 3-Bromo-but-1-yne In acetone for 14h; Reflux;	92%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 6959-47-3
2-chloromethylpyridine hydrochloride

: 123559-29-5
4-(2-pyridylmethoxy)-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; toluene at 110℃; for 20h;	90%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 105-36-2
ethyl bromoacetate

: 934278-64-5
2-[[2,8-bis(trifluoromethyl)-4-quinolinyl]oxy]acetic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: 2,8-bis(trifluoromethyl)quinolin-4-ol With potassium carbonate In acetone for 0.25h; Reflux; Stage #2: ethyl bromoacetate With potassium iodide In acetone for 2h; Williamson synthesis; Reflux;	90%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 590-17-0
cyanomethyl bromide

: 1141427-82-8
2-[[2,8-bis(trifluoromethyl)-4-quinolinyl]oxy]acetonitrile

Conditions

Conditions	Yield
Stage #1: 2,8-bis(trifluoromethyl)quinolin-4-ol With potassium carbonate In acetone for 0.25h; Reflux; Stage #2: cyanomethyl bromide With potassium iodide In acetone for 2h; Williamson synthesis; Reflux;	90%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 105-39-5
chloroacetic acid ethyl ester

: 934278-64-5
2-[[2,8-bis(trifluoromethyl)-4-quinolinyl]oxy]acetic acid ethyl ester

Conditions

Conditions	Yield
With sodium carbonate; potassium iodide at 80℃; for 2h;	89%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 26496-94-6
Ethyl 4-(bromomethyl)benzoate

: 1141427-84-0
4-[[[2,8-bis(trifluoromethyl)-4-quinolinyl]oxy]methyl]benzoic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: 2,8-bis(trifluoromethyl)quinolin-4-ol With potassium carbonate In acetone for 0.25h; Reflux; Stage #2: Ethyl 4-(bromomethyl)benzoate With potassium iodide In acetone for 2h; Williamson synthesis; Reflux;	86%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 108-24-7
acetic anhydride

: C13H7F6NO2

Conditions

Conditions	Yield
In acetone for 3h; Reflux;	85%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

acyl chloride: acyl chloride

: C15H11F6NO3

Conditions

Conditions	Yield
With potassium carbonate In acetone for 3h; Reflux;	84.97%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 41337-81-9
ethyl 6-(hydroxymethyl)pyridine-2-carboxylate

: 1141427-80-6
6-[[[2,8-bis(trifluoromethyl)-4-quinolinyl]oxy]methyl]-2-pyridinecarboxylic acid ethyl ester

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction;	81%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 98-09-9
benzenesulfonyl chloride

: C17H9F6NO3S

Conditions

Conditions	Yield
With potassium carbonate In acetone for 3h; Reflux;	79%

: 2528-00-9
5-Chloromethyl-furan-2-carboxylic acid ethyl ester

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 1141427-85-1
5-[[[2,6-bis(trifluoromethyl)-4-quinolinyl]oxy]methyl]-2-furancarboxylic ethyl ester

Conditions

Conditions	Yield
Stage #1: 2,8-bis(trifluoromethyl)quinolin-4-ol With potassium carbonate In acetone for 0.25h; Reflux; Stage #2: 5-Chloromethyl-furan-2-carboxylic acid ethyl ester With potassium iodide In acetone for 2h; Williamson synthesis; Reflux;	75%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

sulfonyl chloride: sulfonyl chloride

: C12H7F6NO3S

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux;	74.23%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 535-11-5, 41978-69-2
Ethyl 2-bromopropionate

: 934278-65-6
2-(2,8-bis-trifluoromethyl-quinolin-4-yloxy)-propionic acid ethyl ester

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 45℃; for 1h;	74%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 124-63-0
methanesulfonyl chloride

: C12H7F6NO3S

Conditions

Conditions	Yield
With potassium carbonate In acetone for 3h; Reflux;	74%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 138500-85-3
4-bromomethylphenylboronic acid pinacol ester

: 854371-66-7
4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-2,8-bis-trifluoromethyl-quinoline

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	73%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 20782-91-6
2-(bromomethyl)-5-nitrofuran

: 1141427-86-2
4-[(5-nitro)-2-furanylmethoxy]-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
Stage #1: 2,8-bis(trifluoromethyl)quinolin-4-ol With potassium carbonate In acetone for 0.25h; Reflux; Stage #2: 2-(bromomethyl)-5-nitrofuran With potassium iodide In acetone for 2h; Williamson synthesis; Reflux;	71%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

chloroacyl chloride: chloroacyl chloride

amino: amino

: C16H12F6N2O3

Conditions

Conditions	Yield
Stage #1: 2,8-bis(trifluoromethyl)quinolin-4-ol; chloroacyl chloride In acetone for 3h; Reflux; Stage #2: amino With potassium carbonate In ethanol for 3h; Reflux;	67.84%

...Expand

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 140-10-3
(E)-3-phenylacrylic acid

: C20H11F6NO2

Conditions

Conditions	Yield
Stage #1: (E)-3-phenylacrylic acid With thionyl chloride at 80℃; for 4h; Stage #2: 2,8-bis(trifluoromethyl)quinolin-4-ol With triethylamine at 20℃; for 3.6h; Cooling with ice;	67%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 100960-16-5
4-(chloromethyl)thiazole-2-carboxylic acid-ethyl ester

: 5-[[[2,8-bis(trifluoromethyl)-4-quinolinyl]oxy]methyl]-2-thiazolecarboxylic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: 2,8-bis(trifluoromethyl)quinolin-4-ol With potassium carbonate In acetone for 0.25h; Reflux; Stage #2: 4-(chloromethyl)thiazole-2-carboxylic acid-ethyl ester With potassium iodide In acetone for 2h; Williamson synthesis; Reflux;	58%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

iodoalkane: iodoalkane

: 1239667-01-6
4-methoxy-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
With potassium carbonate at 30℃; for 12h;	52.68%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 358-23-6
trifluoromethylsulfonic anhydride

: 2,8-bis(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate

Conditions

Conditions	Yield
With lithium hydroxide In water; toluene at 0 - 20℃;	50%
With lithium hydroxide In water; toluene at 0 - 20℃; for 3h;	50%
With lithium hydroxide In water; toluene at 0 - 20℃; for 3h;	50%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 349120-86-1
2-bromo-N-(3,5-dimethylphenyl)acetamide

: 2-((2,8-bis(trifluoromethyl )quinolin-4-yl)oxy)-N-(3,5-dimethylphenyl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	50%

: 35853-41-9
2,8-bis(trifluoromethyl)quinolin-4-ol

: 74-88-4
methyl iodide

: 1239667-01-6
4-methoxy-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 20h;	50%
With potassium carbonate In acetone for 12h; Reflux;

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

1. Introduction of 2,8-Bis(trifluoromethyl)-4-quinolinol

The 2,8-Bis(trifluoromethyl)-4-quinolinol, with its CAS NO 35853-41-9, is a kind of light grey powder. It has synonyms of 2,8-Bis(Trifluoromethyl)-4-quinolinol;2,8-Bis(trifluoromethyl)-4-hydroxyquinoline and 4-Hydroxy-2,8-bis(trifluoromethyl)quinoline. 2,8-Bis(trifluoromethyl)-4-quinolinol should be stored in shady and cool warehouse.

2. Properties of 2,8-Bis(trifluoromethyl)-4-quinolinol

(1) XLogP3-AA 3.3 (2) H-Bond Donor 1 (3) H-Bond Acceptor 8
(4) Tautomer Count 3 (5) Exact Mass 281.027533 (6) MonoIsotopic Mass 281.027533
(7) Topological Polar Surface Area 29.1 (8) Heavy Atom Count 19
(9) Complexity 410 (10) Covalently-Bonded Unit Count 1 (11) Feature 3D Acceptor Count 1
(12) Feature 3D Donor Count 1 (13) Feature 3D Cation Count 1 (14) Feature 3D Ring Count 2
(15) Effective Rotor Count 2 (16) Conformer Sampling RMSD 0.6 (17) CID Conformer Count 1

3. Structure descriptors of 2,8-Bis(trifluoromethyl)-4-quinolinol

IUPAC Name: 2,8-bis(trifluoromethyl)-1H-quinolin-4-one

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

Canonical SMILES : C1=CC2=C(C(=C1)C(F)(F)F)NC(=CC2=O)C(F)(F)F

4.Safety information of 2,8-Bis(trifluoromethyl)-4-quinolinol

Hazard Codes Irritant Xi
Risk Statements 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S37/39: Wear suitable gloves and eye/face protection
WGK Germany 3
Hazard Note Irritant

5.Toxicity data of 2,8-Bis(trifluoromethyl)-4-quinolinol

RTECS#: CAS# 35853-41-9: None listed
LD50/LC50: RTECS: Not available.
Carcinogenicity: 2,8-BIS(TRIFLUOROMETHYL)-4-QUINOLINOL, 99% - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Other: The toxicological properties have not been fully investigated

Product Name

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

Synthetic route

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

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