Pyridine,2-bromo-5-(trifluoromethoxy)- supplier

Name
2-Bromo-5-trifluoromethoxypyridine
EINECS
CAS No. 888327-36-4
Article Data5
CAS DataBase
Density 1.737 g/cm³
Solubility
Melting Point
Formula C₆H₃BrF₃NO
Boiling Point 194.1 °C at 760 mmHg
Molecular Weight 241.995
Flash Point 71.2 °C
Transport Information
Appearance
Safety 36/37
Risk Codes 43
Molecular Structure
Hazard Symbols
Synonyms Pyridine,2-bromo-5-(trifluoromethoxy);2-BROMO-5-TRIFLUOROMETHOXYPYRIDINE;
PSA 22.12000
LogP 2.74270

Synthetic route

: 1206972-45-3
2-chloro-5-(trifluoromethoxy)pyridine

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

Conditions

Conditions	Yield
With trimethylsilyl bromide In propiononitrile for 24h; Reflux;	81%
With trimethylsilyl bromide In propiononitrile at 100℃; for 72h;	81%

: 55717-45-8
6-bromo-pyridin-3-ol

: 56-23-5
tetrachloromethane

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

Conditions

Conditions	Yield
Stage #1: 6-bromo-pyridin-3-ol; tetrachloromethane With antimony pentafluoride at 150℃; for 8h; Stage #2: With potassium hydroxide In water	2.9%

: 223463-14-7
6-bromopyridin-3-ylboronic acid

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dihydrogen peroxide; acetic acid / tetrahydrofuran / 0 - 20 °C 2: antimony pentafluoride / 8 h / 150 °C View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 407-25-0
trifluoroacetic anhydride

: 2-bromo-5-(trifluoromethoxy)pyridin-1-ium-1-olate

Conditions

Conditions	Yield
With dihydrogen peroxide In dichloromethane; water at 0℃; for 18h;	100%

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 2,2-dimethyl-1-(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-(pyrimidin-5-yl)propan-1-ol

: 2,2-dimethyl-1-(2-methyl-4-(5-(trifluoromethoxy)pyridin-2-yl)phenyl)-1-(pyrimidin-5-yl)propan-1-ol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;	93%

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 667-27-6
Ethyl bromodifluoroacetate

: ethyl 2,2-difluoro-2-(5-(trifluoromethoxy)pyridin-2-yl)acetate

Conditions

Conditions	Yield
With copper In dimethyl sulfoxide at 80℃;	62%

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 124-38-9
carbon dioxide

: 5-(trifluoromethoxy)picolinic acid

Conditions

Conditions	Yield
Stage #1: 2-bromo-5-(trifluoromethoxy)pyridine With n-butyllithium In hexane; toluene at -100 - -78℃; Stage #2: carbon dioxide In hexane; toluene Stage #3: With hydrogenchloride In water pH=4;	60%
Stage #1: 2-bromo-5-(trifluoromethoxy)pyridine With n-butyllithium In hexane; toluene at -78℃; for 2h; Stage #2: carbon dioxide In hexane; toluene Stage #3: With hydrogenchloride In hexane; water; toluene pH=4;	60%

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 1009307-13-4
ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate

: (E)-ethyl 3-(5-(trifluoromethoxy)pyridin-2-yl)acrylate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 110℃; for 0.5h; Microwave irradiation; Sealed tube; Inert atmosphere;	56%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 110℃; for 0.5h; Microwave irradiation;	56%

: 7343-33-1
3-bromo-1H-1,2,4-triazole

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 2-(3-bromo-1H-1,2,4-triazol-1-yl)-5-(trifluoromethoxy)pyridine

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; Microwave irradiation;	31%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; Sealed tube; Microwave irradiation;	31%

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 4068-78-4
methyl 5-chloro-2-hydroxybenzoate

: methyl 5-chloro-2-[[5-(trifluoromethoxy)-2-pyridyl]oxy]benzoate

Conditions

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 19h; Inert atmosphere;	31%

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: tert-butyl 4-[5-(trifluoromethoxy)pyridin-2-yl]piperazine-1-carboxylate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 16h;	28%

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: C14H20N2O3

: C20H22F3N3O4

Conditions

Conditions	Yield
With 15-crown-5; sodium hydride In N,N-dimethyl-formamide; mineral oil at 80℃; for 16h;	19%

: 942070-84-0
5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)oxazole

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 5-(5-(trifluoromethoxy)pyridin-2-yl)oxazole

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran for 16h; Suzuki Coupling; Reflux;	5.1%

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-(2-amino-2-methylcyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride

: N-(2-methyl-2-{[5-(trifluoromethoxy)pyridin-2-yl]amino}cyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 140℃; for 17h; Inert atmosphere;

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-[(1S,2S)-2-aminocyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride

: 2-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethoxy)pyridin-2-yl]amino}cyclopentyl]benzamide

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; for 17h; Sealed tube; Inert atmosphere;

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-[(1S,2S)-2-aminocyclopentyl]-5-chloro-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride

: 5-chloro-2-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethoxy)pyridin-2-yl]amino}cyclopentyl]benzamide

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 120℃; for 0.25h; Inert atmosphere;

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-[(1S,2S)-2-amino-4,4-difluorocyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

: N-[(1S,2S)-4,4-difluoro-2-{[5-(trifluoromethoxy)pyridin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 120℃; for 17h; Inert atmosphere;

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 2,2-difluoro-2-(5-(trifluoromethoxy)pyridin-2-yl)ethanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: copper / dimethyl sulfoxide / 80 °C 2: sodium tetrahydroborate; ethanol / 0.5 h / 20 °C View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 2,2-difluoro-2-(5-(trifluoromethoxy)pyridin-2-yl)ethyltrifluoromethanesulfonate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: copper / dimethyl sulfoxide / 80 °C 2: sodium tetrahydroborate; ethanol / 0.5 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-(1-(2,2-difluoro-2-(5-(trifluoromethoxy)pyridin-2-yl)ethyl)piperidin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: copper / dimethyl sulfoxide / 80 °C 2: sodium tetrahydroborate; ethanol / 0.5 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 60 °C View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-(1-(2,2-difluoro-2-(5-(trifluoromethoxy)pyridin-2-yl)ethyl)piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: copper / dimethyl sulfoxide / 80 °C 2: sodium tetrahydroborate; ethanol / 0.5 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 60 °C 5: sodium hydroxide / water; tetrahydrofuran / 3 h / 60 °C View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-(1-(2,2-difluoro-2-(5-(trifluoromethoxy)pyridin-2-yl)ethyl)piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: copper / dimethyl sulfoxide / 80 °C 2: sodium tetrahydroborate; ethanol / 0.5 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 60 °C 5: sodium hydroxide / water; tetrahydrofuran / 3 h / 60 °C 6: hydrogenchloride / methanol / 0.5 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: copper / dimethyl sulfoxide / 80 °C
2: sodium tetrahydroborate; ethanol / 0.5 h / 20 °C
3: N-ethyl-N,N-diisopropylamine / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 60 °C
5: sodium hydroxide / water; tetrahydrofuran / 3 h / 60 °C
6: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-[2-(1-benzylpiperidin-4-yl)ethyl]piperidine-4-carboxamide

: N-[2-(1-benzylpiperidin-4-yl)ethyl]-1-[5-(trifluoromethoxy)pyridin-2-yl]piperidine-4-carboxamide

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃;

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 6-bromo-(3-trifluoromethoxy)pyridine-2-carbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dihydrogen peroxide / dichloromethane; water / 18 h / 0 °C 2: triethylamine / acetonitrile / 40 h / 80 °C View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 1-[5-(trifluoromethoxy)pyridin-2-yl]piperazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 16 h / 80 °C 2: hydrogenchloride / water; 1,4-dioxane / 4 h / 20 °C View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-[5-[(tert-butyldimethylsilyl)oxy]pyridin-2-yl]-4-[5-(trifluoromethoxy)pyridin-2-yl]piperazine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 16 h / 80 °C 2: hydrogenchloride / water; 1,4-dioxane / 4 h / 20 °C 3: triethylamine / dichloromethane / 16 h / 20 °C View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: N-(5-hydroxypyridin-2-yl)-4-[5-(trifluoromethoxy)pyridin-2-yl]piperazine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 16 h / 80 °C 2: hydrogenchloride / water; 1,4-dioxane / 4 h / 20 °C 3: triethylamine / dichloromethane / 16 h / 20 °C 4: hydrogenchloride / water; tetrahydrofuran / 2 h / 20 °C View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 5-(trifluoromethoxy)-2-(3-vinyl-1H-1,2,4-triazol-1-yl)pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 1 h / 100 °C / Sealed tube; Microwave irradiation 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 0.5 h / 90 °C / Sealed tube; Microwave irradiation View Scheme

: 888327-36-4
2-bromo-5-(trifluoromethoxy)pyridine

: 1094073-72-9
4,4-difluoroazepane

: 4,4-difluoro-1-(5-(trifluoromethoxy)pyridin-2-yl)azepane

Conditions

Conditions	Yield
With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; sodium t-butanolate In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;
With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; sodium t-butanolate In tetrahydrofuran at 25 - 60℃; for 12h; Inert atmosphere;

Pyridine,2-bromo-5-(trifluoromethoxy)- Specification

The Pyridine,2-bromo-5-(trifluoromethoxy)-, with CAS registry number 888327-36-4, has the systematic name of 2-Bromo-5-(trifluoromethoxy)pyridine. Its molecular weight is 241.99. And the chemical formula of this chemical is C₆H₃BrF₃NO.

Physical properties of Pyridine,2-bromo-5-(trifluoromethoxy)-: (1)ACD/LogP: 3.18; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.18; (4)ACD/LogD (pH 7.4): 3.18; (5)ACD/BCF (pH 5.5): 152.57; (6)ACD/BCF (pH 7.4): 152.57; (7)ACD/KOC (pH 5.5): 1272.14; (8)ACD/KOC (pH 7.4): 1272.14; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 22.12 Å²; (13)Index of Refraction: 1.474; (14)Molar Refractivity: 39.16 cm³; (15)Molar Volume: 139.2 cm³; (16)Polarizability: 15.52×10^-24cm³; (17)Surface Tension: 32.4 dyne/cm; (18)Density: 1.737 g/cm³; (19)Flash Point: 71.2 °C; (20)Enthalpy of Vaporization: 41.27 kJ/mol; (21)Boiling Point: 194.1 °C at 760 mmHg; (22)Vapour Pressure: 0.627 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(ncc1OC(F)(F)F)Br
(2)InChI: InChI=1/C6H3BrF3NO/c7-5-2-1-4(3-11-5)12-6(8,9)10/h1-3H
(3)InChIKey: RKXYQQVLVNEAFB-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C6H3BrF3NO/c7-5-2-1-4(3-11-5)12-6(8,9)10/h1-3H
(5)Std. InChIKey: RKXYQQVLVNEAFB-UHFFFAOYSA-N

Product Name

2-Bromo-5-trifluoromethoxypyridine

Synthetic route

Pyridine,2-bromo-5-(trifluoromethoxy)- Specification

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