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About This Item
Empirical Formula (Hill Notation):
C4H3BrN2
CAS Number:
Molecular Weight:
158.98
Beilstein:
107326
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
97%
form
solid
mp
67-73 °C (lit.)
functional group
bromo
SMILES string
Brc1cncnc1
InChI
1S/C4H3BrN2/c5-4-1-6-3-7-2-4/h1-3H
InChI key
GYCPLYCTMDTEPU-UHFFFAOYSA-N
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General description
Rapid nucleophilic displacement reactions of 5-bromopyrimidine with nucleophiles under microwave irradiation has been studied. 5-Bromopyrimidine undergoes direct metallation with lithuium diisopropylamide to yield 4-lithio-5-bromopyrimidine.
Application
5-Bromopyrimidine was used in the synthesis of:
- N-heteroaryl substituted 9-arylcarbazolyl derivatives via palladium-catalyzed aerobic and ligand-free Suzuki reaction
- (5-(phenylethynyl)pyrimidine) via microwave assisted organic synthesis (MAOS) Sonogashira protocol
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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A palladium-catalyzed aerobic and ligand-free Suzuki reaction in aqueous ethanol has been developed for the synthesis of N-heteroaryl substituted 9-arylcarbazolyl derivatives. A number of N-heteroaryl halides, namely 2-halogenated pyridines, 2-bromoquinoline, 5-bromopyrimidine and 2-chloropyrazine, were coupled with 4-(9H-carbazol-9-yl)phenylboronic acid (CPBA) or
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