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

Name
2,8-BIS(TRIFLUOROMETHYL)-4-BROMOQUINOLINE
EINECS 609-183-7
CAS No. 35853-45-3
Article Data15
CAS DataBase
Density 1.72g/cm³
Solubility
Melting Point 62-64 °C(lit.)
Formula C11H4 Br F6 N
Boiling Point 281.6°Cat760mmHg
Molecular Weight 344.054
Flash Point 124.1°C
Transport Information
Appearance
Safety Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39
WGK Germany 3
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols
Synonyms 2,8-Bis(trifluoromethyl)-4-bromoquinoline;4-Bromo-2,8-bis(trifluoromethyl)quinoline;
PSA 12.89000
LogP 5.03490

Synthetic route

: 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%

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

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

Conditions

Conditions	Yield
With phosphorus; bromine In acetic acid at 25℃; for 4h;	80%

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

: 40320-60-3
N-benzhydryl 3-azetidinone

: 260972-91-6
3-(2,8-bis(trifluoromethyl)-4-quinolinyl)-1-diphenylmethyl-3-azetidinol

Conditions

Conditions	Yield
With n-butyllithium In water	100%

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

: 106-45-6
para-thiocresol

: 177092-30-7
2,8-bis(trifluoromethyl)-4-quinolyl p-tolylsulphide

Conditions

Conditions	Yield
With potassium hydroxide In methanol; ethanol at 60℃; for 2h;	95%

: 12093-10-6
ferrocenecarboxaldehyde

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

: [2,8-bis(trifluoromethyl)quinolin-4-yl]ferrocenemethanol

Conditions

Conditions	Yield
Stage #1: (2,8-bis-trifluoromethyl)-4-bromoquinoline With n-butyllithium In diethyl ether; hexane at -78℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: ferrocenecarboxaldehyde In diethyl ether; hexane at -78℃; for 2h; Inert atmosphere; Schlenk technique;	94%

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

: sodium vinyl trifluoroborate

: 1031928-53-6
2,8-bis(trifluoromethyl)-4-vinylquinoline

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 Suzuki Coupling;	94%

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

: 544-92-3
copper(I) cyanide

: 2,8-bis(trifluoromethyl)quinoline-4-carbonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Substitution; Heating;	93%

: 110-85-0
piperazine

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

: 4-(piperazin-1-yl)-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
With potassium carbonate; triethylamine at 135℃; for 4h;	92%

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

: 1241848-96-3
1-acetoxy-1'-(1,3-dioxan-2-yl)ferrocene

: 1381984-20-8
1-(1,3-dioxan-2-yl)-1'-(2,8-bis(trifluoromethyl)quinolin-4-yloxy)-ferrocene

Conditions

Conditions	Yield
Stage #1: 1-acetoxy-1'-(1,3-dioxan-2-yl)ferrocene With sodium methylate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: (2,8-bis-trifluoromethyl)-4-bromoquinoline In N,N-dimethyl-formamide at 150℃; for 6h; Inert atmosphere; Schlenk technique;	92%

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

: 124-38-9
carbon dioxide

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

Conditions

Conditions	Yield
With n-butyllithium In diethyl ether at -35℃; for 0.333333h;	86%

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

: 1258291-33-6
4-azido-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 90℃; for 1h;	85%

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

: 6336-45-4
vinylboronic acid dibutyl ester

: 1031928-53-6
2,8-bis(trifluoromethyl)-4-vinylquinoline

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium hydroxide In water; toluene for 24h; Suzuki-Miyaura coupling; Inert atmosphere; Reflux;	82%
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere; Reflux;	82%
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere; Reflux;	82%

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

: 107-19-7
propargyl alcohol

: 3-(2,8-bis(trifluoromethyl)quinolin-4-yl)prop-2-yn-1-ol

Conditions

Conditions	Yield
Stage #1: propargyl alcohol With triethylamine for 0.0833333h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: (2,8-bis-trifluoromethyl)-4-bromoquinoline With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide for 4h; Reflux;	80%

: 6859-99-0
3-hydroxypiperazine

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

: 1092355-84-4
4-(3-hydroxypiperidine-1-yl)-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 2h;	78%

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

: 66507-25-3
ruthenocene carboxylaldheyde

: [2,8-bis(trifluoromethyl)quinolin-4-yl]ruthenocenemethanol

Conditions

Conditions	Yield
Stage #1: (2,8-bis-trifluoromethyl)-4-bromoquinoline With n-butyllithium In diethyl ether; hexane at -78℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: ruthenocene carboxylaldheyde In diethyl ether; hexane at -78℃; for 2h; Inert atmosphere; Schlenk technique;	78%

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

: (E)-2-(6-(4,4,5,5-tetramethylmethyl-1,3,2-dioxaborolan-2-yl)-hex-5-en-1-yl)isoindoline-1,3-dione

: (E)-2-(6-(2,8-bis(trifluoromethyl)quinolin-4-yl)hex-5-en-1-yl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; XPhos In tetrahydrofuran; water for 5h; Suzuki Coupling; Reflux; Inert atmosphere;	77%

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

: C20H26BNO4

: C25H18F6N2O2

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; XPhos In tetrahydrofuran; water Reflux;	77%

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

: 736147-22-1
bis(2,8-bis-trifluoromethyl quinolyl) disulphide

Conditions

Conditions	Yield
With potassium ethyldithiocarbamate In DMF (N,N-dimethyl-formamide) at 20℃; for 10h;	75%
With potassium ethyldithiocarbamate In DMF (N,N-dimethyl-formamide) at 20℃; for 10h;	75%

: 40499-83-0
pyrrolidin-3-ol

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

: 1092355-83-3
4-(3-hydroxypyrrolidin-1-yl)-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 2h;	75%

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

: 7486-35-3
tri-n-butyl(vinyl)tin

: 1031928-53-6
2,8-bis(trifluoromethyl)-4-vinylquinoline

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In acetonitrile at 90℃; for 4h; Stille coupling; Inert atmosphere; Sealed tube;	75%
With tetrabutylammomium bromide; potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 90℃; for 4h; Product distribution / selectivity; Stille Coupling; Inert atmosphere; Sealed tube;	75%
With tetrabutylammomium bromide; potassium carbonate; bis(triphenylphosphine)palladium(II) dichloride In acetonitrile at 90℃; for 4h; Product distribution / selectivity; Stille Coupling reaction; Inert atmosphere;	75%

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

: potassium vinyltrifluoroborate

: 1031928-53-6
2,8-bis(trifluoromethyl)-4-vinylquinoline

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In tetrahydrofuran; water for 24h; Suzuki-Miyaura coupling; Inert atmosphere; Reflux;	71%
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;	71%
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran; water for 24h; Product distribution / selectivity; Stille Coupling reaction; Inert atmosphere; Reflux;	71%

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

: 52898-33-6
N-(5-hexenyl)phthalimide

: C25H19F6N3O2

Conditions

Conditions	Yield
With 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 110℃; Reagent/catalyst;	68%

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

: 52898-33-6
N-(5-hexenyl)phthalimide

: (E)-2-(6-(2,8-bis(trifluoromethyl)quinolin-4-yl)hex-5-en-1-yl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With AD-mix-β; palladium diacetate; triethylamine; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In N,N-dimethyl-formamide at 110℃; Reagent/catalyst; Inert atmosphere;	68%

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

: 98437-24-2
benzofuran-2-boronic acid

: 260972-85-8
4-(2-Benzofuranyl)-2,8-bis(trifluoromethyl)quinoline

Conditions

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water	64%

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

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

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

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78℃;	64%
Stage #1: (2,8-bis-trifluoromethyl)-4-bromoquinoline With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at -78℃; for 3h;	37%
Stage #1: (2,8-bis-trifluoromethyl)-4-bromoquinoline With n-butyllithium In diethyl ether at -78℃; Stage #2: N,N-dimethyl-formamide In diethyl ether at -78℃;	29%
With n-butyllithium at -78℃; Inert atmosphere;
Stage #1: (2,8-bis-trifluoromethyl)-4-bromoquinoline With n-butyllithium at -78℃; Inert atmosphere; Stage #2: N,N-dimethyl-formamide Inert atmosphere;	10 g

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

: 150521-32-7
(S)-1-N-Boc-piperidine-2-al

: 1309854-88-3
(S)-tert-butyl 2-((R)-(2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: (2,8-bis-trifluoromethyl)-4-bromoquinoline With n-butyllithium In diethyl ether at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: (S)-1-N-Boc-piperidine-2-al In diethyl ether at -78℃; for 0.333333h; Inert atmosphere; Schlenk technique; stereoselective reaction;	58%

: 1-phenyl-6-tributylstannyl-3,4-dihydropyrrolo[1,2-a]pyrazine

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

: 1-phenyl-6-(2,8-bis(trifluoromethyl)quinolin-4-yl)-3,4-dihydropyrrolo[1,2-a]pyrazine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In tetrahydrofuran for 20h; Stille coupling; Heating;	56%

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

: 2450-71-7
Propargylamine

: 1257629-75-6
N-(2-propyn-1-yl)-[2,8-bis(trifluoromethyl)]-4-quinolinylamine

Conditions

Conditions	Yield
In 1,4-dioxane Reflux;	45%

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

: 155269-97-9
4-allyl-1-benzoylpiperidine

: 155269-98-0
1-benzoyl-4-<(E)-3-<2,8-bis(trifluoromethyl)-4-quinolinyl>allyl>piperidine

Conditions

Conditions	Yield
With palladium diacetate; copper(l) iodide; tributyl-amine; triphenyl-o-tolylphosphine In N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃; for 20h;	42%

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

: (S,S,p-S)-(-)-1-acetoxy-2-(4-methoxymethyl-1,3-dioxan-2-yl)ferrocene

: (2S,4S)-1-(2,8-bis(trifluoromethyl)quinolin-4-yloxy)-2-(4-methoxymethyl-1,3-dioxan-2-yl)ferrocene

Conditions

Conditions	Yield
Stage #1: (S,S,p-S)-(-)-1-acetoxy-2-(4-methoxymethyl-1,3-dioxan-2-yl)ferrocene With sodium methylate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Stage #2: (2,8-bis-trifluoromethyl)-4-bromoquinoline In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	32%

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

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

The 2,8-Bis(trifluoromethyl)-4-bromoquinoline, with its CAS NO 35853-45-3, is a kind of yellow solid. It has synonyms of 2,8-Bis(trifluoromethyl)-4-bromoquinoline and 4-Bromo-2,8-bis(trifluoromethyl)quinoline. 2,8-Bis(trifluoromethyl)-4-bromoquinoline should be stored in shady and cool warehouse and mainly used as pharmaceutical intermediate.

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

(1) Polar Surface Area: 12.89 Å2 (2) Index of Refraction: 1.51 (3) Molar Refractivity: 59.83 cm3
(4) Molar Volume: 199.9 cm3 (5) Polarizability: 23.72 ×10-24 cm3 (6) Surface Tension: 30.5 dyne/cm
(7) Density: 1.72 g/cm3 (8) Flash Point: 124.1 °C (9) Enthalpy of Vaporization: 49.95 kJ/mol
(10) Boiling Point: 281.6 °C at 760 mmHg (11) Vapour Pressure: 0.00603 mmHg at 25°C

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

IUPAC Name: 4-bromo-2,8-bis(trifluoromethyl)quinoline

InChI: InChI=1S/C11H4BrF6N/c12-7-4-8(11(16,17)18)19-9-5(7)2-1-3-6(9)10(13,
14)15/h1-4H

InChIKey: DXALAFAFIXJDOS-UHFFFAOYSA-N

Canonical SMILES : C1=CC2=C(C(=C1)C(F)(F)F)N=C(C=C2Br)C(F)(F)F

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

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

Product Name

2,8-BIS(TRIFLUOROMETHYL)-4-BROMOQUINOLINE

Synthetic route

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

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Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
WGK Germany	3