150649
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:
Molecular Weight:
190.00
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
218-806-8
Beilstein/REAXYS Number:
127286
MDL number:
Assay:
99%
Form:
solid
InChI key
QFVKLKDEXOWFSL-UHFFFAOYSA-N
InChI
1S/C4H4BrN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
SMILES string
NC1=NC(=O)NC=C1Br
assay
99%
form
solid
mp
240-243 °C (dec.) (lit.)
functional group
bromo
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.
signalword
Danger
hcodes
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
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
Kiyohiko Kawai et al.
Journal of the American Chemical Society, 126(40), 12843-12846 (2004-10-08)
A series of naphthalimide (NI)- and 5-bromocytosine ((br)C)-modified oligodeoxynucleotides (ODNs) were prepared, and their lifetimes of the charge-separated states during the photosensitized one-electron oxidation of DNA were measured. Various lifetimes of the charge-separated states were observed depending on the sequence
Haizheng Hong et al.
Journal of the American Chemical Society, 127(40), 13969-13977 (2005-10-06)
Here, we showed that Pyrex-filtered UV light irradiation of d((Br)CA) gave rise to three types of intrastrand cross-link products, that is, d(C[5-N6]A), d(C[5-2]A), and d(C[5-8]A), where the C5 carbon atom of cytosine is covalently bonded to the N6 nitrogen atom
B Lakatos et al.
FEMS microbiology letters, 171(2), 161-165 (1999-03-17)
The transport of radioactively labelled uracil into submerged mycelium of T. viride was measured by means of a membrane filtration technique. It was found to be time-dependent (up to 90 min) and concentration-dependent (up to 8 mmol l-1). Its concentration
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
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