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219142

Sigma-Aldrich

5-Bromopyrimidine

97%

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About This Item

Empirical Formula (Hill Notation):
C4H3BrN2
CAS Number:
4595-59-9
Molecular Weight:
158.98
Beilstein:
107326
EC Number:
224-992-1
MDL number:
MFCD00006117
UNSPSC Code:
12352100
PubChem Substance ID:
24853108
NACRES:
NA.22

Quality Level

100

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
03311KV
01514BI
14806JF
13211TB
04215DG

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Sigma-Aldrich

131695

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Sigma-Aldrich

B70202

4-Bromoisoquinoline

The new NHS: restricting GPs' access to x ray services.
J Bahrami et al.
BMJ (Clinical research ed.), 302(6791), 1541-1541 (1991-06-22)
Direct metalation of pyrimidine. Synthesis of some 4-substituted pyrimidines.
Kress TJ.
The Journal of Organic Chemistry, 44(13), 2081-2082 (1979)
Efficient nucleophilic substitution reactions of pyrimidyl and pyrazyl halides with nucleophiles under focused microwave irradiation.
Cherng,Y-J.
Tetrahedron, 58(5), 887-890 (2002)
Xiaofeng Rao et al.
Organic & biomolecular chemistry, 10(39), 7875-7883 (2012-08-15)
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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