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Sigma-Aldrich

5-Bromocytosine

99%

Synonym(s):

4-Amino-5-bromo-2-hydroxypyrimidine

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About This Item

Empirical Formula (Hill Notation):
C4H4BrN3O
CAS Number:
2240-25-7
Molecular Weight:
190.00
Beilstein/REAXYS Number:
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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
L Yang et al.
Biophysical chemistry, 76(1), 25-34 (1999-02-24)
Three triple-helical hairpin DNAs with substitution of 5-bromocytosine for cytosine in different strands have been investigated by molecular mechanics and Raman spectroscopy. The stability of the three substituted triplexes were compared with the corresponding unsubstituted triplex DNA by the molecular
D B Tippin et al.
Journal of molecular biology, 267(5), 1171-1185 (1997-04-18)
The A-DNA decamer d(CCGGGCCm5CGG) crystallizes in the presence of spermine in three polymorphic forms and with one duplex in the asymmetric unit: hexagonal (P6(1)), unit cell of 55.0 A x 55.0 A x 45.9 A; orthorhombic (P2(1)2(1)2(1)), unit cell of
M Liu et al.
Journal of biomolecular structure & dynamics, 15(5), 895-903 (1998-06-10)
Three triplex DNAs containing 5-bromocytosine[BrC] were studied by vibrational spectroscopy and molecular modelling. Firstly, three oligodeoxypyrimidines of 5'-(TC)3-T4-(BrCT)3 [CBrC], 5'-(TBrC)3-T4-(CT)3 [BrCC] and 5'-(TBrC)3-T4-(BrCT)3 [BrCBrC] were synthesized and then reacted with an oligodeoxypurine of 5'-(AG)3 at pH=4.5 in phosphate buffer respectively
Yu Zeng et al.
Journal of the American Chemical Society, 126(21), 6552-6553 (2004-05-27)
Pyrex-filtered UV light irradiation of d(BrCG) and 5-bromocytosine-containing duplex DNA leads to facile formation of a cross-link lesion between the C5 carbon atom of cytosine and the C8 carbon atom of its adjacent guanine. A similar cross-link lesion has been
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