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

Base Information

• Chemical Name: 4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine
• CAS No.: 188416-28-6
• Molecular Formula: C6H5BrClFN2
• Molecular Weight: 239.475
• Hs Code.: 2933599590
• European Community (EC) Number: 811-268-0
• DSSTox Substance ID: DTXSID90940340
• Mol file: 188416-28-6.mol

Synonyms:188416-28-6;4-(1-bromoethyl)-6-chloro-5-fluoropyrimidine;6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine;6-(1-Bromo-ethyl)-4-chloro-5-fluoropyrimidine;188416-30-0;4-chloro-5-fluoro-6-(1-bromoethyl)-pyrimidine;C6H5BrClFN2;SCHEMBL824165;DTXSID90940340;AAESVRBYUDTWKH-UHFFFAOYSA-N;BCP04244;MFCD08458246;AKOS015892507;AC-9024;AM84648;CS-0001499;FT-0651931;A24992;F19199;Pyrimidine,4-(1-bromoethyl)-6-chloro-5-fluoro-;J-517977;Pyrimidine, 4-(1-bromoethyl)-6-chloro-5-fluoro-;4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine

Chemical Property of 4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine

Chemical Property:

• Vapor Pressure: 0.023mmHg at 25°C
• Refractive Index: 1.556
• Boiling Point: 257.85 °C at 760 mmHg
• PKA: -2.62±0.35(Predicted)
• Flash Point: 109.744 °C
• PSA: 25.78000
• Density: 1.725 g/cm³
• LogP: 2.72500
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 237.93087
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=C(C(=NC=N1)Cl)F)Br

Technology Process of 4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine

There total 6 articles about 4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-chloro-6-ethyl-5-fluoropyrimidine (137234-74-3) → 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane (188416-28-6)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In dichloromethane; at 55 ℃; for 16h; Temperature;

Reference yield:

2,4-dichloro-6-ethyl-5-fluoropyrimidine (137234-85-6) → 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane (188416-28-6)

Guidance literature:

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

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); 5%-palladium/activated carbon; hydrogen; triethylamine; sodium hydroxide; trichlorophosphate; In ethanol; dichloromethane; water;

DOI:10.1021/op0000879

Reference yield:

2-chloro-6-ethyl-5-fluoro-4-hydroxypyrimidine ammonium salt → 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane (188416-28-6)

Guidance literature:

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

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); 5%-palladium/activated carbon; hydrogen; triethylamine; trichlorophosphate; In ethanol; dichloromethane;

DOI:10.1021/op0000879

upstream raw materials:

4-chloro-6-ethyl-5-fluoropyrimidine

2,4-dichloro-6-ethyl-5-fluoropyrimidine

6-ethyl-5-fluoro-4-hydroxypyrimidine

2-fluoro-3-oxopentanoic acid ethyl ester

Downstream raw materials:

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

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate

voriconazole

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

Refernces

• 1、 -. "A 4 - (1-bromo-ethyl) - 5-fluoro-6-chloro-pyrimidine synthesis method". Paragraph 0023; 0033; 0040; 0041. . Retrieved 2017/02/23.
• 2、 -. "Novel Compound Having Angiogenesis Inhibitory Activity, Method for Preparing Same, and Pharmaceutical Composition Comprising Same". Paragraph 0204; 0205. . Retrieved 2014/09/29.