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150649

Sigma-Aldrich

5-Bromocytosine

99%

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Synonym(s):
4-Amino-5-bromo-2-hydroxypyrimidine
Empirical Formula (Hill Notation):
C4H4BrN3O
CAS Number:
2240-25-7
Molecular Weight:
190.00
Beilstein:
127286
EC Number:
218-806-8
MDL number:
MFCD00056025
UNSPSC Code:
12352100
PubChem Substance ID:
24849050
NACRES:
NA.22

Assay

99%

form

solid

mp

240-243 °C (dec.) (lit.)

SMILES string

NC1=NC(=O)NC=C1Br

InChI

1S/C4H4BrN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)

InChI key

QFVKLKDEXOWFSL-UHFFFAOYSA-N

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General description

5-Bromocytosine derivative (β isomer) is a potent anti-HIV agent.

Application

5-Bromocytosine was used in the synthesis of five cross-link products- C[5-N6]A, C[5-2]A, C[5-8]A, A[2-5]C, and A[8-5]C, under both aerobic and anaerobic conditions.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H317,H318,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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L S Jeong et al.
Journal of medicinal chemistry, 36(18), 2627-2638 (1993-09-03)
The beta-D-(2S,5R)- and alpha-D-(2S,5S)-1,3-oxathiolanylpyrimidine and -purine nucleosides with natural nucleoside configuration were synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells. The key intermediate 14, which was utilized for the synthesis of various nucleosides, was synthesized from
M Ortiz-Lombardía et al.
Nature structural biology, 6(10), 913-917 (1999-10-03)
DNA recombination is a universal biological event responsible both for the generation of genetic diversity and for the maintenance of genome integrity. A four-way DNA junction, also termed Holliday junction, is the key intermediate in nearly all recombination processes. This
Rodrigo Varas et al.
Brain research, 1072(1), 72-78 (2006-01-13)
Petrosal ganglion neurons are depolarized and fire action potentials in response to acetylcholine and nicotine. However, little is known about the subtype(s) of nicotinic acetylcholine receptors involved, although alpha4 and alpha7 subunits have been identified in petrosal ganglion neurons. Cytisine
Kristin A Seiberling et al.
International forum of allergy & rhinology, 2(1), 80-84 (2012-02-09)
One theory for the pathogenesis of chronic rhinosinusitis with nasal polyps (CRSwNP) involves aberration in the expression of genes that maintain the sinonasal innate immune system. We propose that the alteration in gene expression seen in CRSwNP is a result
C M Nunn
Journal of biomolecular structure & dynamics, 14(1), 49-55 (1996-08-01)
The crystal structure of the DNA decamer d(AGGBrCATGCCT) has been determined to a resolution of 2.0 A and R factor of 19.6%. Crystals of d(AGGBrCATGCCT) were grown in the presence of cobalt hexammine but no cobalt hexammine ions are bound
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