6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine supplier

Name
6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine
EINECS
CAS No. 188416-28-6
Article Data9
CAS DataBase
Density 1.725 g/cm³
Solubility
Melting Point
Formula C₆H₅BrClFN₂
Boiling Point 257.85 °C at 760 mmHg
Molecular Weight 239.475
Flash Point 109.744 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine;
PSA 25.78000
LogP 2.72500

Synthetic route

: 137234-74-3
4-chloro-5-fluoro-6-ethylpyrimidine

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

Conditions

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane at 55℃; for 16h; Temperature;	98%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 12h; Reflux;	95.1%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 12h; Reflux;	95.1%

: 137234-85-6
2,4-dichloro-6-ethyl-5-fluoropyrimidine

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water / 0.5 h / 80 - 90 °C 1.2: pH 1 2.1: 5%-palladium/activated carbon; hydrogen / ethanol / 50 °C / 2585.81 Torr 3.1: triethylamine; trichlorophosphate / dichloromethane / 8 h / 40 °C / Reflux 4.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 12 h / Inert atmosphere; Reflux View Scheme

: 2-chloro-6-ethyl-5-fluoro-4-hydroxypyrimidine ammonium salt

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 5%-palladium/activated carbon; hydrogen / ethanol / 50 °C / 2585.81 Torr 2: triethylamine; trichlorophosphate / dichloromethane / 8 h / 40 °C / Reflux 3: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 12 h / Inert atmosphere; Reflux View Scheme

: 137234-87-8
6-ethyl-5-fluoro-4-hydroxypyrimidine

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; trichlorophosphate / dichloromethane / 8 h / 40 °C / Reflux 2: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 12 h / Inert atmosphere; Reflux View Scheme

: 759-67-1
2-fluoro-3-oxopentanoic acid ethyl ester

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium methylate / methanol / 20 h / 15 °C 2: trichlorophosphate / 3 h / 60 °C 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / 1,2-dichloro-ethane / 15 h / 50 °C View Scheme

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: 188416-35-5
3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Conditions

Conditions	Yield
With lead; samarium diiodide; 1-benzyl-3-(2-pyridylmethyl)-1H-benzimidazolium chloride; iodine; zinc In tetrahydrofuran at -5 - 40℃; for 1.33333h; Inert atmosphere;	87%
With zinc(II) chloride Reformatsky Reaction;
With hydrogenchloride; zinc In tetrahydrofuran; water

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: 188416-20-8
3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride salt

Conditions

Conditions	Yield
Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane; 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone With lead; iodine; zinc In tetrahydrofuran at 5 - 25℃; Reformatsky Reaction; Inert atmosphere; Stage #2: With hydrogenchloride In isopropyl alcohol at 25℃;	48.7%
Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane; 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone With lead; bromine; zinc In tetrahydrofuran; dichloromethane at 15 - 50℃; Inert atmosphere; Stage #2: With hydrogenchloride In isopropyl alcohol; acetone at 20 - 25℃; for 2h; Concentration;
With bromine; zinc(II) chloride; zinc In tetrahydrofuran at 15℃; Temperature; Reagent/catalyst; Inert atmosphere;

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: 3-(6-chloro-5-fluoro-4-pyrimidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol hydrochloride

Conditions

Conditions	Yield
Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane; 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone With lead; chloro-trimethyl-silane; zinc In tetrahydrofuran at 0 - 5℃; for 1.5h; Inert atmosphere; Stage #2: With isopropyl alcohol hydrogen chloride In ethyl acetate at 20℃; for 3h;	57.37%

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 1028563-57-6
1-(2,4-difluorophenyl)-2-(1H-tetrazol-1-yl)ethanone

A: (2S,3R)-3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-tetrazol-1-yl)butan-2-ol

B: (2R,3S)-3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-tetrazol-1-yl)butan-2-ol

Conditions

Conditions	Yield
With iodine; zinc; lead In tetrahydrofuran at 0 - 20℃; for 3.16667h;

...Expand

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: (2R,3S/2S,3R)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride

Conditions

Conditions	Yield
Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane; 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone With lead; iodine; acetic acid; zinc In tetrahydrofuran; water at 0 - 5℃; Inert atmosphere; Stage #2: With hydrogenchloride In water; ethyl acetate; isopropyl alcohol	61.9%
Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane; 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone With lead; iodine; zinc In tetrahydrofuran at 5 - 25℃; Reformatsky Reaction; Inert atmosphere; Stage #2: With hydrogenchloride In isopropyl alcohol at 25℃;	48.7%
Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane; 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone With lead; bromine; zinc In tetrahydrofuran; dichloromethane at 30 - 50℃; Stage #2: With hydrogenchloride In isopropyl alcohol at 20 - 25℃; for 4h; Product distribution / selectivity;

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: (2RS,3SR)-2-(2,4-difluorophenyl)-3-(6-chloro-5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride

Conditions

Conditions	Yield
Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane With pyridine; zinc/copper couple; Cinchonin In tetrahydrofuran at -5℃; for 2h; Inert atmosphere; Stage #2: 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone In tetrahydrofuran at 0 - 5℃; for 12h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.166667h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere;	90%

Yield

Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane With pyridine; zinc/copper couple; Cinchonin In tetrahydrofuran at -5℃; for 2h; Inert atmosphere;
Stage #2: 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone In tetrahydrofuran at 0 - 5℃; for 12h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.166667h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere;

90%

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: (2R,3R/2S,3S)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazole-1-yl)butan-2-ol

Conditions

Conditions	Yield
With iodine In tetrahydrofuran
With iodine In tetrahydrofuran

: 7439-92-1
lead

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: (2R,3R/2S,3S)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazole-1-yl)butan-2-ol

Conditions

Conditions	Yield
With iodine In tetrahydrofuran

...Expand

: 7439-92-1
lead

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 6381-92-6
edetate disodium dihydrate

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: 7440-66-6
zinc

: (2R,3R/2S,3S)-3-(4-Chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; iodine In tetrahydrofuran; water; acetic acid; ethyl acetate; isopropyl alcohol

...Expand

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lead; zinc; bromine / dichloromethane; tetrahydrofuran / 30 - 50 °C 1.2: 4 h / 20 - 25 °C 2.1: sodium hydroxide / water; methanol / 20 - 25 °C / pH 8 - 9 2.2: 55 - 60 °C 2.3: 1 h / 40 - 45 °C 3.1: sodium hydroxide / dichloromethane; water / 15 - 25 °C / pH 10 - 11 View Scheme
Multi-step reaction with 4 steps 1.1: zinc; lead / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 2.1: sodium hydroxide / water; dichloromethane / pH 11 2.2: 25 °C / 775.74 Torr 3.1: methanol; acetone / Reflux 4.1: sodium hydroxide / water; dichloromethane / pH 11 View Scheme
Multi-step reaction with 4 steps 1.1: zinc; lead / tetrahydrofuran / 16 °C / Inert atmosphere; Reflux 2.1: sodium hydroxide / water; dichloromethane / pH 11 2.2: 25 °C / 775.74 Torr 3.1: methanol; acetone / Reflux 4.1: sodium hydroxide / water; dichloromethane / pH 11 View Scheme

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

A: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

B: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane; 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone With zinc(II) chloride; zinc In tetrahydrofuran at -5 - 5℃; for 1h; Stage #2: With ammonium formate; zinc In methanol at 20℃; for 16h; Stage #3: Product distribution / selectivity; Heating / reflux;

...Expand

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: zinc; lead / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 2.1: sodium hydroxide / water; dichloromethane / pH 11 2.2: 25 °C / 775.74 Torr View Scheme
Multi-step reaction with 2 steps 1.1: zinc; lead / tetrahydrofuran / 16 °C / Inert atmosphere; Reflux 2.1: sodium hydroxide / water; dichloromethane / pH 11 2.2: 25 °C / 775.74 Torr View Scheme
Multi-step reaction with 2 steps 1: zinc; lead; iodine; acetic acid / tetrahydrofuran; water / 0 - 5 °C / Inert atmosphere 2: ammonium formate; palladium 10% on activated carbon; water / methanol / 4 h / 60 °C View Scheme

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 1420998-90-8
N-(3-chlorophenyl)-2-(4-piperidylamino)nicotinamide

: 1420999-05-8
2-{1-[1-(6-chloro-5-fluoropyrimidin-4-yl)ethyl]piperidin-4-ylamino}-N-(3-chlorophenyl)pyridine-3-carboxamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	48%

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: 3-(6-chloro-5-fluoro-4-pyrimidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol hydrochloride

: 3-(6-chloro-5-fluoro-4-pyrimidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol hydrochloride

C: C22H18ClF4N7O

Conditions

Conditions	Yield
With lead; zinc In tetrahydrofuran at 16℃; Reagent/catalyst; Temperature; Inert atmosphere; Reflux;	A 47.5 %Chromat. B 24 %Chromat. C 9.2 %Chromat.

...Expand

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 188416-34-4, 137234-71-0
(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: zinc; lead / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 2.1: sodium hydroxide / water; dichloromethane / pH 11 2.2: 25 °C / 775.74 Torr 3.1: methanol; acetone / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: zinc; lead / tetrahydrofuran / 16 °C / Inert atmosphere; Reflux 2.1: sodium hydroxide / water; dichloromethane / pH 11 2.2: 25 °C / 775.74 Torr 3.1: methanol; acetone / Reflux View Scheme

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: 3-(6-chloro-5-fluoro-4-pyrimidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol hydrochloride

: 3-(6-chloro-5-fluoro-4-pyrimidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol hydrochloride

Conditions

Conditions	Yield
With lead; zinc In tetrahydrofuran for 1h; Reagent/catalyst; Temperature; Inert atmosphere; Reflux; Overall yield = 65 %; Overall yield = 7.89 g;	A n/a B n/a

...Expand

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: voriconazole L-camphorsulfate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lead; zinc; bromine / dichloromethane; tetrahydrofuran / 30 - 50 °C 1.2: 4 h / 20 - 25 °C 2.1: sodium hydroxide / water; methanol / 20 - 25 °C / pH 8 - 9 2.2: 55 - 60 °C 2.3: 1 h / 40 - 45 °C View Scheme

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: (2RS,3SR)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: zinc/copper couple; pyridine; Cinchonin / tetrahydrofuran / 2 h / -5 °C / Inert atmosphere 1.2: 12 h / 0 - 5 °C / Inert atmosphere 1.3: 0.17 h / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen; sodium carbonate / ethanol / 20 - 25 °C / 760.05 Torr View Scheme

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: voriconazole L-camphor sulfonate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: zinc/copper couple; pyridine; Cinchonin / tetrahydrofuran / 2 h / -5 °C / Inert atmosphere 1.2: 12 h / 0 - 5 °C / Inert atmosphere 1.3: 0.17 h / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen; sodium carbonate / ethanol / 20 - 25 °C / 760.05 Torr 3.1: methanol; acetone / Reflux View Scheme

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: iodine; zinc; lead; samarium diiodide; 1-benzyl-3-(2-pyridylmethyl)-1H-benzimidazolium chloride / tetrahydrofuran / 1.33 h / -5 - 40 °C / Inert atmosphere 2.1: sodium acetate; 5%-palladium/activated carbon; hydrogen / methanol / 25 °C / 760.05 Torr 2.2: 2 h / Reflux View Scheme

6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine Chemical Properties

Product Name: 6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine
Synonyms of 6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine (CAS NO.188416-28-6): 4-Chloro-5-fluoro-6-(1-bromoethyl)-pyrimidine
CAS NO: 188416-28-6
Molecular Formula of 6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine (CAS NO.188416-28-6): C₆H₅BrClFN₂
Molecular Weight: 239.4727
Molecular Structure:

H bond acceptors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 25.78 Å²
Index of Refraction: 1.556
Molar Refractivity: 44.608 cm³
Molar Volume: 138.789 cm³
Surface Tension: 48.341 dyne/cm
Density of 6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine (CAS NO.188416-28-6): 1.725 g/cm³
Flash Point: 109.744 °C
Enthalpy of Vaporization: 47.542 kJ/mol
Boiling Point: 257.85 °C at 760 mmHg
Vapour Pressure: 0.023 mmHg at 25°C

Product Name

6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine

Synthetic route

6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine Chemical Properties

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