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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

219142-VAR:
219142-5G:
219142-100G:
219142-BULK:
219142-25G:

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Certificates of Analysis (COA)

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

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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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