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188416-28-6

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Basic Information
CAS No.: 188416-28-6
Name: 6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine
Article Data: 9
Molecular Structure:
Molecular Structure of 188416-28-6 (6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine)
Formula: C6H5BrClFN2
Molecular Weight: 239.475
Synonyms: 4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine;
Density: 1.725 g/cm3
Boiling Point: 257.85 °C at 760 mmHg
Flash Point: 109.744 °C
PSA: 25.78000
LogP: 2.72500
Related products
Synthetic route
137234-74-3

4-chloro-5-fluoro-6-ethylpyrimidine

188416-28-6

1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;
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Chemistry

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