63931-21-5

Basic information

• Product Name: 5-Bromo-2,4,6-trichloropyrimidine
• Synonyms: 5-Bromo-2,4,6-trichloropyrimidine
• CAS NO: 63931-21-5
• Molecular Formula: C₄BrCl₃N₂
• Molecular Weight: 262.33
• Mol File: 63931-21-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 286.602 °C at 760 mmHg
• Flash Point: 127.133 °C
• Appearance: /
• Density: 2.051 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -8.56±0.39(Predicted)
• CAS DataBase Reference: 5-Bromo-2,4,6-trichloropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2,4,6-trichloropyrimidine(63931-21-5)
• EPA Substance Registry System: 5-Bromo-2,4,6-trichloropyrimidine(63931-21-5)

Safety Data

• Hazardous Substances Data: 63931-21-5(Hazardous Substances Data)

Usage

Description

5-Bromo-2,4,6-trichloropyrimidine is an organic compound characterized by the presence of a pyrimidine ring with a bromine atom at the 5th position and three chlorine atoms at the 2nd, 4th, and 6th positions. This halogenated pyrimidine derivative exhibits unique chemical properties and reactivity, making it a valuable intermediate in the synthesis of various pyrimidine-based compounds.

Uses

Used in Pharmaceutical Industry:
5-Bromo-2,4,6-trichloropyrimidine is used as a key intermediate in the preparation of pyrimidine derivatives, specifically as Aβ42 inhibitors. These inhibitors are designed to target and reduce the aggregation of amyloid-beta 42 peptides, which are implicated in the pathogenesis of Alzheimer's disease. By inhibiting the formation of toxic Aβ42 aggregates, these pyrimidine-based compounds have the potential to mitigate the progression of neurodegenerative disorders and improve the quality of life for affected individuals.

Synthetic route

4-fluoroaniline (371-40-4) + 5-bromo-2,4,6-trichloropyrimidine (63931-21-5) → 5-bromo-2,6-dichloro-N-(4-fluorophenyl)pyrimidin-4-amine

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 20 - 25℃; for 18h;	90%
With sodium acetate In tetrahydrofuran; water at 20℃; for 18h;	90%

5-bromo-2,4,6-trichloropyrimidine (63931-21-5) + 3,4-difluoroaniline (3863-11-4) → 5-bromo-2,6-dichloro-N-(3,4-difluorophenyl)pyrimidin-4-amine

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 20 - 25℃; for 18h;	86%

3-(trifluoromethyl)-bicyclo[1.1.1]pentan-1-amine hydrochloride (262852-11-9) + 5-bromo-2,4,6-trichloropyrimidine (63931-21-5) → 5-bromo-2,6-dichloro-N-(3-(trifluoromethyl)bicyclo[1.1.1]pentan-1-yl)pyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 25℃; for 7h;	80%

2-chloro-4-fluoroaniline (2106-02-7) + 5-bromo-2,4,6-trichloropyrimidine (63931-21-5) → 5-bromo-2,6-dichloro-N-(2-chloro-4-fluorophenyl)pyrimidin-4-amine

Conditions	Yield
Stage #1: 2-chloro-4-fluoroaniline With lithium hexamethyldisilazane In tetrahydrofuran; ethylbenzene at 0 - 5℃; for 0.25h; Stage #2: 5-bromo-2,4,6-trichloropyrimidine With lithium hexamethyldisilazane In tetrahydrofuran; ethylbenzene at 0 - 25℃; for 18h;	79%

3,3-difluorocyclobutylamine hydrochloride (637031-93-7) + 5-bromo-2,4,6-trichloropyrimidine (63931-21-5) → 5-bromo-2,6-dichloro-N-(3,3-difluorocyclobutyl)pyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 25℃; for 7h;	73%

2,4-difluorophenylamine (367-25-9) + 5-bromo-2,4,6-trichloropyrimidine (63931-21-5) → 5-bromo-2,6-dichloro-N-(2,4-difluorophenyl)pyrimidin-4-amine

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 20 - 25℃; for 18h;	69%

4-fluoro-N-(3-methylbut-3-en-1-yl)aniline + 5-bromo-2,4,6-trichloropyrimidine (63931-21-5) → 5-bromo-2,6-dichloro-N-(4-fluorophenyl)-N-(3-methylbut-3-en-1-yl)pyrimidin-4-amine

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 20 - 25℃; for 18h;	61%

2,3-difluoroanilline (4519-40-8) + 5-bromo-2,4,6-trichloropyrimidine (63931-21-5) → 5-bromo-2,6-dichloro-N-(2,3-difluorophenyl)pyrimidin-4-amine

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 20 - 25℃; for 18h;	42%

3-amino-6-chloropyridine-2<1H>-thione (27467-92-1) + 5-bromo-2,4,6-trichloropyrimidine (63931-21-5) → 2,4,7-trichloro-10H-pyrido[2,3-b]pyrimido[4,5-e][1,4]thiazine (63931-19-1)

Conditions	Yield
With sulfuric acid; sodium sulfite Heating;

5-amino-6-methoxypyridine-2<1H>-thione (42362-14-1) + 5-bromo-2,4,6-trichloropyrimidine (63931-21-5) → 2,4-dichloro-7-methoxy-10H-pyrido[2,3-b]pyrimido[4,5-e][1,4]thiazine (63931-17-9)

Conditions	Yield
With sulfuric acid; sodium sulfite Heating;

Downstream Products

• 63931-19-1 2,4,7-Trichlor-1,3,6-triazaphenothiazin 
• 63931-17-9 2,4-Dichlor-7-methoxy-1,3,6-triazaphenothiazin 
• 2171305-26-1 5-bromo-2,6-dichloro-N-(3,4-difluorophenyl)pyrimidin-4-amine