3-Bromo-2,6-dichloropyridine supplier

Name
3-Bromo-2,6-dichloropyridine
EINECS
CAS No. 866755-20-6
Density 1.848 g/cm³
Solubility
Melting Point 68-71 °C
Formula C₅H₂BrCl₂N
Boiling Point 254.972 °C at 760 mmHg
Molecular Weight 226.888
Flash Point 108.003 °C
Transport Information UN 2811
Appearance
Safety 26-39-45
Risk Codes 25-37/38-41
Molecular Structure
Hazard Symbols Xi
Synonyms 3-bromo-2,6-dichloropyridine
PSA 12.89000
LogP 3.15090

Synthetic route

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 124-41-4
sodium methylate

: 3 -bromo-6-chloro-2-methoxypyridine

Conditions

Conditions	Yield
With methanol In acetonitrile	93%

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 2516-33-8
Cyclopropylmethanol

: C9H9BrClNO

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 80℃;	80%

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 2042-14-0
4-methyl-5-nitrophenol

: 3-bromo-6-chloro-2-(4-methyl-3-nitrophenoxy)pyridine

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide for 8h; Heating; regioselective reaction;	70%
With caesium carbonate In N,N-dimethyl-formamide for 8h; Heating;	70%

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 80392-79-6
3-bromo-2,6-difluoropyridine

Conditions

Conditions	Yield
With cesium fluoride In dimethyl sulfoxide at 80℃; for 8h;	64%

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 141699-55-0
tert-butyl 3-hydroxyazetidine-1-carboxylate

: tert-butyl 3-((3-bromo-6-chloropyridin-2-yl)oxy)azetidine-1-carboxylate

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; for 16h;	58.23%

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 389890-43-1
tert-butyl (1,3-cis)-N-(3-hydroxycyclobutyl)carbamate

: 1349184-97-9
tert-butyl ((1S,3S)-3-((3-bromo-6-chloropyridin-2-yl)oxy)cyclobutyl)carbamate

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	56%

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 62-53-3
aniline

A: 3-bromo-6-chloro-N-phenylpyridin-2-amine

B: 5-bromo-6-chloro-N-phenylpyridin-2-amine

Conditions

Conditions	Yield
With 1,1'-bis[bis(dimethylamino)phosphino]ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane at 70℃; for 15h; Sealed tube; Inert atmosphere;	A 50% B 27%

...Expand

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 3-bromo-6-chloro-2-hydrazinylpyridine

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol at 80℃; for 18h;	44%

: 109-01-3
1-methyl-piperazine

: 866755-20-6
3-bromo-2, 6-dichloropyridine

A: 1418153-18-0
1-(3-bromo-6-chloropyridin-2-yl)-4-methylpiperazine

B: 1418153-33-9
1-(5-bromo-6-chloropyridin-2-yl)-4-methylpiperazine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 140℃; for 1h; Inert atmosphere;	A 30% B 8%

...Expand

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: C15H12

: C20H13Cl2N

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 60℃; for 5h; Inert atmosphere;	10%

: 866755-20-6
3-bromo-2, 6-dichloropyridine

A: N-benzyl-5-bromo-6-fluoropyridin-2-amine

B: N-benzyl-3-bromo-6-fluoropyridin-2-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: cesium fluoride / dimethyl sulfoxide / 8 h / 80 °C 2: potassium carbonate / dimethyl sulfoxide / 2 h / 20 °C View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 64-17-5
ethanol

A: 1310416-63-7
3-bromo-2,6-diethoxypyridine

B: 3-bromo-2-chloro-6-ethoxypyridine

C: 3-bromo-6-chloro-2-ethoxypyridine

Conditions

Conditions	Yield
With sodium at 70℃; Overall yield = 87 %; Overall yield = 930 mg;

...Expand

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 3-bromo-2-ethoxy-6-((4-methoxybenzyl)oxy)pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium / 70 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 2.2: 80 °C View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 1-(4-(2-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)-3-(4-((3-methyloxetan-3-yl)oxy)-3-(trifluoromethyl)phenyl)urea

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium / 70 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 2.2: 80 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane; water / 0.25 h / 110 °C / Microwave irradiation View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 1-(4-(2-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-3-(4-((3-methyloxetan-3-yl)oxy)-3-(trifluoromethyl)phenyl)urea

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium / 70 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 2.2: 80 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane; water / 0.25 h / 110 °C / Microwave irradiation 4.1: trifluoroacetic acid / dichloromethane / 25 °C 4.2: pH 7 View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: C9H12BrN3O

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / acetonitrile / 80 °C 2: hydrazine hydrate / 90 °C View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: C10H10BrN3O2

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / acetonitrile / 80 °C 2: hydrazine hydrate / 90 °C 3: acetonitrile / 4 h / 60 °C View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 5-(cyclopropylmethoxy)-6-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / acetonitrile / 80 °C 2: hydrazine hydrate / 90 °C 3: acetonitrile / 4 h / 60 °C 4: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.83 h / 140 °C / Microwave irradiation View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: N-(2-fluoro-6-methoxybenzyl)-8-(5-methyl-1,3,4-oxadiazol-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: hydrazine hydrate / ethanol / 18 h / 80 °C 2.1: 1.5 h / 110 °C 3.1: ethanol / 8 h / 85 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile / 18 h / 90 °C / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / 12 h / 85 °C / 11400.8 Torr 6.1: lithium hydroxide monohydrate; water / methanol; tetrahydrofuran / 2 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine; isopropyl chloroformate / dichloromethane / 1 h / 20 °C 7.2: 18 h / 20 °C 8.1: trichlorophosphate / 3 h / 110 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: hydrazine hydrate / ethanol / 18 h / 80 °C
2.1: 1.5 h / 110 °C
3.1: ethanol / 8 h / 85 °C
4.1: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile / 18 h / 90 °C / Inert atmosphere
5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / 12 h / 85 °C / 11400.8 Torr
6.1: lithium hydroxide monohydrate; water / methanol; tetrahydrofuran / 2 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine; isopropyl chloroformate / dichloromethane / 1 h / 20 °C
7.2: 18 h / 20 °C
8.1: trichlorophosphate / 3 h / 110 °C
View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 8-(5-ethyl-1,2,4-oxadiazol-3-yl)-N-(2-fluoro-6-methoxybenzyl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: hydrazine hydrate / ethanol / 18 h / 80 °C 2: 1.5 h / 110 °C 3: ethanol / 8 h / 85 °C 4: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile / 18 h / 90 °C / Inert atmosphere 5: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 120 °C 6: hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine / ethanol / 18 h / 90 °C 7: toluene / 18 h / 125 °C 8: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: hydrazine hydrate / ethanol / 18 h / 80 °C
2: 1.5 h / 110 °C
3: ethanol / 8 h / 85 °C
4: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile / 18 h / 90 °C / Inert atmosphere
5: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 120 °C
6: hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine / ethanol / 18 h / 90 °C
7: toluene / 18 h / 125 °C
8: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C
View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: N-(2-fluoro-6-methoxybenzyl)-8-(3-methyl-1,2,4-oxadiazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: hydrazine hydrate / ethanol / 18 h / 80 °C 2.1: 1.5 h / 110 °C 3.1: ethanol / 8 h / 85 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile / 18 h / 90 °C / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / 12 h / 85 °C / 11400.8 Torr 6.1: lithium hydroxide monohydrate; water / methanol; tetrahydrofuran / 2 h / 20 °C 7.1: 1,1'-carbonyldiimidazole / dichloromethane / 2 h / 20 °C 7.2: 18 h / 20 °C 8.1: tetrabutyl ammonium fluoride / acetonitrile / 2 h / 20 °C 9.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: hydrazine hydrate / ethanol / 18 h / 80 °C
2.1: 1.5 h / 110 °C
3.1: ethanol / 8 h / 85 °C
4.1: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile / 18 h / 90 °C / Inert atmosphere
5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / 12 h / 85 °C / 11400.8 Torr
6.1: lithium hydroxide monohydrate; water / methanol; tetrahydrofuran / 2 h / 20 °C
7.1: 1,1'-carbonyldiimidazole / dichloromethane / 2 h / 20 °C
7.2: 18 h / 20 °C
8.1: tetrabutyl ammonium fluoride / acetonitrile / 2 h / 20 °C
9.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C
View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 8-(2,4-dimethylpyrimidin-5-yl)-6-fluoro-N-(2-fluoro-6-methoxybenzyl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrazine hydrate / ethanol / 18 h / 80 °C 2: 1.5 h / 110 °C 3: ethanol / 8 h / 85 °C 4: Selectfluor / methanol; acetonitrile / 0.25 h / 20 °C 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / water; 1,4-dioxane / 0.67 h / 110 °C / Sealed tube; Inert atmosphere View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: N-(2,3-difluoro-6-methoxybenzyl)-8-(4-((dimethylamino)methyl)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 18 h / 80 °C 2: 1.5 h / 110 °C 3: sodium hydrogencarbonate / water; 1,4-dioxane / 16 h / 95 °C / Inert atmosphere 4: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate; XPhos / 1,4-dioxane / 2 h / 120 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 4 steps
1: hydrazine hydrate / ethanol / 18 h / 80 °C
2: 1.5 h / 110 °C
3: sodium hydrogencarbonate / water; 1,4-dioxane / 16 h / 95 °C / Inert atmosphere
4: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate; XPhos / 1,4-dioxane / 2 h / 120 °C / Inert atmosphere
View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: N-(2-fluoro-6-methoxybenzyl)-8-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 18 h / 80 °C 2: 1.5 h / 110 °C 3: ethanol / 8 h / 85 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / water; 1,4-dioxane / 1 h / 90 °C / Inert atmosphere View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: N-(2-fluoro-6-methoxybenzyl)-8-(2-methylpyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 18 h / 80 °C 2: 1.5 h / 110 °C 3: ethanol / 8 h / 85 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 5 h / 120 °C / Inert atmosphere; Sealed tube View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 8-(2,4-dimethylpyrimidin-5-yl)-N-(2-fluoro-6-methoxybenzyl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 18 h / 80 °C 2: 1.5 h / 110 °C 3: ethanol / 8 h / 85 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / water; 1,4-dioxane / 1 h / 110 °C / Inert atmosphere View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: N-(2-fluoro-6-methoxybenzyl)-8-(2-isobutyl-4-methylpyrimidin-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 18 h / 80 °C 2: 1.5 h / 110 °C 3: ethanol / 8 h / 85 °C 4: sodium hydrogencarbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 8-bromo-5-chloro-[1,2,4]triazolo[4,3-a]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 18 h / 80 °C 2: 1.5 h / 110 °C View Scheme

: 866755-20-6
3-bromo-2, 6-dichloropyridine

: 8-bromo-N-(2-fluoro-6-methoxybenzyl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / ethanol / 18 h / 80 °C 2: 1.5 h / 110 °C 3: ethanol / 8 h / 85 °C View Scheme

3-Bromo-2,6-dichloropyridine Specification

The IUPAC name of 3-Bromo-2,6-dichloropyridine is 3-bromo-2,6-dichloropyridine. With the CAS registry number 866755-20-6, it is also named as Pyridine,3-bromo-2,6-dichloro-. The product's category is Heterocyclic Compounds. Besides, it is cream-coloured powder, which should be stored in a sealed, cool, dry place. In addition, its molecular formula is C₅H₂BrCl₂N and molecular weight is 226.89.

The other characteristics of 3-Bromo-2,6-dichloropyridine can be summarized as: (1)ACD/LogP: 3.05; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.05; (4)ACD/LogD (pH 7.4): 3.05; (5)ACD/BCF (pH 5.5): 122.503; (6)ACD/BCF (pH 7.4): 122.503; (7)ACD/KOC (pH 5.5): 1087.188; (8)ACD/KOC (pH 7.4): 1087.188; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 12.89 Å²; (13)Index of Refraction: 1.597; (14)Molar Refractivity: 41.824 cm³; (15)Molar Volume: 122.743 cm³; (16)Polarizability: 16.58×10^-24cm³; (17)Surface Tension: 48.344 dyne/cm; (18)Density: 1.848 g/cm³; (19)Flash Point: 108.003 °C; (20)Melting Point: 68-71 °C; (21)Enthalpy of Vaporization: 47.252 kJ/mol; (22)Boiling Point: 254.972 °C at 760 mmHg; (23)Vapour Pressure: 0.027 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: c1cc(nc(c1Br)Cl)Cl
(2)InChI: InChI=1/C5H2BrCl2N/c6-3-1-2-4(7)9-5(3)8/h1-2H
(3)InChIKey: PZHASTRIYXMWKM-UHFFFAOYAJ
(4)Std. InChI: InChI=1S/C5H2BrCl2N/c6-3-1-2-4(7)9-5(3)8/h1-2H
(5)Std. InChIKey: PZHASTRIYXMWKM-UHFFFAOYSA-N

Product Name

3-Bromo-2,6-dichloropyridine

Synthetic route

3-Bromo-2,6-dichloropyridine Specification

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