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5-Bromouridine

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Identification
Molecular formula
C9H11BrN2O6
CAS number
957-75-5
IUPAC name
5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
State
State
At room temperature, 5-Bromouridine is typically in a solid state, specifically a powder. It is stable under recommended storage conditions, which are generally cool and dry environments to prevent any degradation due to moisture or excessive heat.
Melting point (Celsius)
215.00
Melting point (Kelvin)
488.15
Boiling point (Celsius)
471.15
Boiling point (Kelvin)
744.30
General information
Molecular weight
321.09g/mol
Molar mass
321.0390g/mol
Density
0.5800g/cm3
Appearence

5-Bromouridine appears as a white to almost white crystalline powder. It is usually odorless and has a slightly bitter taste.

Comment on solubility

Solubility of 5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

The solubility of the compound C9H11BrN2O6, also known as 5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione, can be characterized by several key factors:

  • Polarity: The presence of multiple hydroxyl groups (-OH) contributes to the overall polarity of the molecule, making it more soluble in polar solvents like water.
  • Hydrogen Bonding: The ability of hydroxyl groups to form hydrogen bonds enhances solubility in aqueous environments, promoting better interaction with water molecules.
  • Structural Considerations: The cyclic structure of the tetrahydrofuran moiety may influence solubility. Compounds with rigid structures may show decreased solubility compared to flexible analogs.

In general, one might expect the compound to have moderate to good solubility in polar solvents, while demonstrating limited solubility in nonpolar solvents due to the hydrophilic nature imparted by its functional groups. **Understanding the solubility profile** is crucial for applications such as drug formulation and bioavailability assessments. Thus, careful analysis in relevant solvents is recommended to predict its behavior in various chemical environments.

Interesting facts

Interesting Facts About 5-Bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

This compound is a fascinating example of a pyrimidine derivative which incorporates both halogen (bromine) and carbohydrate-like structures in its molecular design. Such combinations make it of great interest in various fields of research, especially in medicinal chemistry.

Key Features

  • Structural Complexity: The presence of a bromine atom on the pyrimidine ring introduces unique reactivity profiles that can be harnessed in synthetic organic chemistry.
  • Bioactivity: Compounds like this one often demonstrate biological activity that may be useful in pharmaceuticals, especially in antibiotic and antiviral applications.
  • Stereochemistry: The stereochemical configuration with specific chiral centers as indicated in its name, provides insights into its potential interactions with biological targets, which often depend on three-dimensional orientation.

5-Bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione serves as an illustrative case in studying the integration of heterocyclic compounds with sugar analogues, forging pathways for discovering new therapeutic agents.

As a scientist, one might reflect on the importance of such compounds, stating, "The intersection of heterocycles and carbohydrate chemistry opens a realm of possibilities for innovation in drug development." This compound exemplifies not only the inherent complexity found in molecular chemistry but also the potential it holds for advancing health sciences.

Synonyms
5-BROMO-2'-DEOXYURIDINE
59-14-3
Broxuridine
Bromodeoxyuridine
5-Bromodeoxyuridine
5-BrdU
BRDU
BUDR
5-Bromouracil deoxyriboside
Broxuridina
5-Bromodesoxyuridine
Bromouracil deoxyriboside
5-Bromo-2-deoxyuridine
Broxuridinum
5-Bdu
5-Bromouracil-2-deoxyriboside
Broxuridine [INN]
Uridine, 5-bromo-2'-deoxy-
NSC-38297
C9H11BrN2O5
Broxuridinum [INN-Latin]
Broxuridina [INN-Spanish]
Bromoouridine
Radibud
Brudr
CCRIS 818
HSDB 7477
Broxuridine [INN:JAN]
CHEBI:472552
EINECS 200-415-9
MFCD00006529
5-Budr
5-Bromo-dURD
BRN 0030395
5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
DTXSID7033105
G34N38R2N1
5-Bromo-2'-deoxyuridine (BRDU)
BROXURIDINE [MI]
BROXURIDINE [JAN]
5-Bromo-1-(2-deoxy-beta-D-ribofuranosyl)uracil
BROXURIDINE [HSDB]
5-bromo-2'-deoxy uridine
BROXURIDINE [MART.]
BROXURIDINE [WHO-DD]
CHEMBL222280
DTXCID5013105
NSC 38297
4-24-00-01234 (Beilstein Handbook Reference)
5-Bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
brdurd
NCGC00090770-05
Broxuridinum (INN-Latin)
Broxuridina (INN-Spanish)
BROXURIDINE (MART.)
BDU
CAS-59-14-3
5 Bromodeoxyuridine
SMR001227189
2'-deoxy-5-bromouridine
Deoxyriboside, Bromouracil
5 Bromo 2' deoxyuridine
5-bromo-2'-desoxyuridine
(+)-5-Bromo-2'-deoxyuridine
Broxine
Neomark
UNII-G34N38R2N1
5-bromo-1-(4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
5-bromo-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
5-Bromo-2'-deoxyuridine(BRDU)
5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
5-brom-2'-desoxyuridin
Broxuridine (JAN/INN)
Maybridge4_003385
Epitope ID:138105
cid_6035
5-Bromo-2 inverted exclamation marka-deoxyuridine
Lopac0_000212
SCHEMBL27755
MLS001055406
MLS002153366
5-Bromo-2'-deoxyuridine, 97%
Uridine, 5-bromo-2'-deoxy-()
HMS1619B05
HMS3039G15
HMS3260L05
BCP21681
5-BROMO-2''-DEOXY URIDINE
Tox21_111016
Tox21_200106
Tox21_500212
BDBM50207303
HB0979
HG1160
STL530083
AKOS001715166
AKOS016015753
AKOS037495737
Tox21_111016_1
CCG-204307
DB12028
LP00212
NB06315
SDCCGSBI-0050200.P002
BrdU (5-Bromo-2′-deoxyuridine)
NCGC00090770-01
NCGC00090770-02
NCGC00090770-03
NCGC00090770-04
NCGC00090770-06
NCGC00090770-07
NCGC00090770-08
NCGC00090770-09
NCGC00090770-14
NCGC00175901-01
NCGC00257660-01
NCGC00260897-01
1-[(4S,2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-bromo-1,3-dihydropyrim idine-2,4-dione
5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
AS-11762
BP-58665
HY-15910
5-Bromo-2'-deoxyuridine, >=99% (HPLC)
B1575
EU-0100212
NS00034095
5-Bromo-2'-deoxyuridine, BioUltra, >=99%
B 5002
D01763
EN300-7376709
Q419861
SR-01000075718
SR-01000075718-1
2'-Deoxy-5-bromouridine;5-Bromo-2'-deoxy-D-uridine
BRD-K79095980-001-09-6
Br-dU; 5-Bromo-1-(2-deoxy-beta-D-ribofuranosyl)uracil
Carbobenzoxy-valyl-alanyl-aspartyl-[O-methyl]-fluoromethylketone
(+)-5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]- pyrimidine-2,4-dione
5-bromo-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-4-hydroxypyrimidin-2(1H)-one
200-415-9
5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyridine-2,4(1H,3H)-dione
5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione