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303526

Sigma-Aldrich

2-Amino-5-bromopyrimidine

98%

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About This Item

Empirical Formula (Hill Notation):
C4H4BrN3
CAS Number:
Molecular Weight:
174.00
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

mp

241-243 °C (lit.)

functional group

bromo

SMILES string

Nc1ncc(Br)cn1

InChI

1S/C4H4BrN3/c5-3-1-7-4(6)8-2-3/h1-2H,(H2,6,7,8)

InChI key

UHRHPPKWXSNZLR-UHFFFAOYSA-N

General description

Crystal structure of 2-amino-5-bromopyrimidine was studied.

Application

2-Amino-5-bromopyrimidine was employed:
  • in synthesis of pyridine, pyrimidine and pyridinone C-nucleoside phosphoramidites
  • in synthesis of 2-phthalimido-5-bromopyrimidine
  • as intermediate for the preparation of sulfanilamides and amino acids containing the pyrimidine ring system. The products are potential antiviral agents

pictograms

Exclamation markEnvironment

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Self-assembly of 1-and 2-dimensional multicompartmental arrays via the 2-aminopyrimidine H-bonding motif and selective guest inclusion.
Krische MJ, et al.
Tetrahedron, 56(36), 6701-6706 (2000)
Jun Lu et al.
The Journal of organic chemistry, 74(21), 8021-8030 (2009-10-02)
In the structures of the HDV ribozyme a cytosine nucleobase resides at the active site poised to participate directly in catalysis. Defining the functional role of the nucleobase requires nucleoside analogues that perturb the functional groups in a strategic manner.
Journal of Chemical Education, 62, 905-905 (1985)
Structure of 2-amino-5-bromopyrimidine.
Watton HLL, et al.
Acta Crystallographica Section C, Crystal Structure Communications, 44(10), 1857-1858 (1988)

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