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5-Fluorouracil

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Identification
Molecular formula
C4H3FN2O2
CAS number
51-21-8
IUPAC name
5-fluoro-1H-pyrimidine-2,4-dione
State
State

At room temperature, 5-fluorouracil is a solid. Its crystalline nature makes it fairly stable under standard temperature and pressure conditions.

Melting point (Celsius)
282.00
Melting point (Kelvin)
555.15
Boiling point (Celsius)
282.00
Boiling point (Kelvin)
555.15
General information
Molecular weight
130.08g/mol
Molar mass
130.0800g/mol
Density
1.4436g/cm3
Appearence

The compound, 5-fluorouracil, typically appears as a white to practically white crystalline powder. It is odorless and has a slightly bitter taste. The solid form can be visually characterized by its fine, crystalline nature.

Comment on solubility

Solubility of 5-fluoro-1H-pyrimidine-2,4-dione (C4H3FN2O2)

The solubility of 5-fluoro-1H-pyrimidine-2,4-dione showcases interesting characteristics pertinent to its molecular structure. This compound contains a fluorine atom and a pyrimidine ring, both of which play significant roles in influencing its solubility in various solvents.

General Solubility Characteristics

  • Polar Solvents: 5-fluoro-1H-pyrimidine-2,4-dione is generally more soluble in polar solvents, such as water and alcohols, due to its ability to engage in hydrogen bonding.
  • Nonpolar Solvents: The solubility is likely to decrease significantly in nonpolar solvents, as the hydrophobic characteristics of the carbon backbone and the fluorine substituent do not favor interaction with these types of solvents.
  • pH Sensitivity: The solubility may also be pH-dependent. In acidic or basic environments, the ionization of the compound can lead to enhanced solubility due to the increased polarity of the ions formed.

Conclusion

In summary, while the exact solubility information of 5-fluoro-1H-pyrimidine-2,4-dione might vary based on environmental conditions, it can be noted that:

  • It is expected to exhibit good solubility in polar solvents.
  • Its solubility in nonpolar solvents is likely to be quite low.
  • Acidic or basic conditions could potentially increase its solubility through ionization.

Understanding the solubility of this compound is crucial in various applications, especially in pharmaceutical and chemical research, where its interactions in different environments can have significant implications.

Interesting facts

Interesting Facts about 5-Fluoro-1H-pyrimidine-2,4-dione

5-Fluoro-1H-pyrimidine-2,4-dione, a noteworthy compound in the realm of organic chemistry, showcases the dynamic interplay between fluorine substitution and the pyrimidine ring structure. Here are some compelling facts about this intriguing molecule:

  • Pyrimidine Derivative: This compound is a derivative of pyrimidine—a six-membered aromatic ring containing two nitrogen atoms. The presence of both carbon and nitrogen plays a critical role in the compound's reactivity and stability.
  • Fluorine's Influence: The substitution of fluorine at the 5-position of the pyrimidine ring alters its electronic properties, which can enhance biological activity, making it an essential component in medicinal chemistry.
  • Biological Relevance: Compounds related to this structure have been investigated for their potential as pharmacological agents, particularly in the development of anticancer drugs and antiviral therapies.
  • Synthetic Pathways: The synthesis of 5-fluoro-1H-pyrimidine-2,4-dione can involve various methodologies, such as the reaction of an appropriate fluorinated precursor with a urea or ureide compound. This aspect underscores the versatility of organic synthesis techniques.
  • Analytical Techniques: Advanced analytical methods like NMR and mass spectrometry are often employed to characterize this compound, providing insights into its structure and purity.

In summary, 5-fluoro-1H-pyrimidine-2,4-dione is more than just a chemical entity; it is a gateway to exploring new therapeutic avenues and understanding the complexities of aromatic nitrogen-containing compounds. As noted by indomitable chemist, "The beauty of organic chemistry lies in the myriad functionalities that a single molecular framework can offer."


Synonyms
5-Fluorouracil
fluorouracil
51-21-8
5-FU
Fluoroplex
Efudex
Adrucil
Carac
Fluracil
Fluoroblastin
Queroplex
5-fluoropyrimidine-2,4(1H,3H)-dione
Phthoruracil
Carzonal
Kecimeton
Fluril
Fluracilum
Timazin
Arumel
Efudix
Ulup
5-Fluoracil
Fluorouracilum
5-fluoro-1H-pyrimidine-2,4-dione
Fluro Uracil
5 Fluorouracil
5-Fluoruracil
Fluorouracilo
Ftoruracil
Fluri
5-Fluoro-2,4(1H,3H)-pyrimidinedione
Effluderm (free base)
Fluroblastin
5-Fluoropyrimidine-2,4-dione
Efurix
Fluoro-uracile
Fluoro-uracilo
Uracil, 5-fluoro-
Ro 2-9757
5-Faracil
Cinco FU
Fluorouracile
2,4(1H,3H)-Pyrimidinedione, 5-fluoro-
2,4-Dihydroxy-5-fluoropyrimidine
5-fluoro-uracil
5-Fluor-2,4-pyrimidindiol
5-fluoropyrimidine-2,4-diol
2,4-Dioxo-5-fluoropyrimidine
Fluorouricil
NSC-19893
5-Fluoropyrimidin-2,4-diol
5-fluoro uracil
5-Ftouracyl
5-Fluoro-2,4-pyrimidinedione
NSC 19893
Fluorouracil Cream
5-Fluor-2,4-dihydroxypyrimidin
Fluorouracil, 5-
Ro-2-9757
U-8953
Fluorouracilum [INN-Latin]
Fluorouracilo [INN-Spanish]
Fluouracil
CCRIS 2582
Tolak
191047-65-1
Fluoro Uracil
HSDB 3228
5-Fluracil
EINECS 200-085-6
FU
5-Fluor-2,4(1H,3H)-pyrimidindion
UNII-U3P01618RT
5 FU
5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
DTXSID2020634
CHEBI:46345
AI3-25297
U3P01618RT
NSC19893
MFCD00006018
Ro-29757
5FU
CHEMBL185
2,4-Pyrimidinediol, 5-fluoro- (9CI)
DTXCID40634
MLS000069498
191047-64-0
191115-88-5
Phtoruracil
EC 200-085-6
URF
Fluorouracil [USAN:USP:INN:BAN:JAN]
NCGC00015442-02
Effluderm
SMR000038082
Fluorouracile [DCIT]
5-Fluoracil [German]
5-Fluoracyl
5-Fluoruracil [German]
Fluorouracilum (INN-Latin)
Fluorouracilo (INN-Spanish)
FLUOROURACIL (MART.)
FLUOROURACIL [MART.]
1004-03-1
FLUOROURACIL (USP-RS)
FLUOROURACIL [USP-RS]
5-FLUOROURACIL (IARC)
5-FLUOROURACIL [IARC]
Flurablastin
FLUOROURACIL (EP MONOGRAPH)
FLUOROURACIL [EP MONOGRAPH]
FLUOROURACIL (USP MONOGRAPH)
FLUOROURACIL [USP MONOGRAPH]
CAS-51-21-8
Fluoroplex (TN)
5-Fluor-2,4-pyrimidindiol [Czech]
Fluorouracil (USAN:USP:INN:BAN:JAN)
Adrucil (TN)
Carac (TN)
FLUCYTOSINE IMPURITY A (EP IMPURITY)
FLUCYTOSINE IMPURITY A [EP IMPURITY]
5-Fluor-2,4-dihydroxypyrimidin [Czech]
SR-01000075881
5-Fluor-2,4(1H,3H)-pyrimidindion [Czech]
inhibits thymilidate synthetase
AccuSite
2,4-Dioxo-5-fluoropryimidine
5-fluorourasil
5-florouracil
5-fluorouacil
5 Fluorouracilum
5-FU (TN)
1upf
5F-uracil
U 8953
Fluorouracil; 5-Fluoropyrimidine-2,4(1H,3H)-dione; Flucytosine Imp. A (EP); Flucytosine Impurity A
Adrucil (ICN)
2794-13-0
Adrucil (Fluorouracil)
Spectrum_000841
Opera_ID_134
5-Fluorouracil, 99%
Spectrum2_000076
Spectrum3_000434
Spectrum4_000557
Spectrum5_000718
WLN: T6MVMVJ EF
FLUOROURACIL [MI]
Lopac-F-6627
F0151
5-Fluorouracil (5-FU)
FLUOROURACIL [INN]
FLUOROURACIL [JAN]
5-Fluorouracil (Standard)
UPCMLD-DP130
F 6627
FLUOROURACIL [HSDB]
FLUOROURACIL [USAN]
SCHEMBL3646
5-fluorpyrimidin-2,4-diol
FLUOROURACIL [VANDF]
Folfox component fluorouracil
Lopac0_000536
BSPBio_002048
FLUCYTOSINE IMPURITY A
KBioGR_001253
KBioSS_001321
2(1H)-Pyrimidinone, 5-fluoro-4-hydroxy- (9CI)
4(3H)-Pyrimidinone, 5-fluoro-2-hydroxy- (9CI)
MLS002415705
DivK1c_000054
FLUOROURACIL [WHO-DD]
FLUOROURACIL [WHO-IP]
SPECTRUM1500305
SPBio_000291
EMTRICITABINE IMPURITY F
5-fluoro-2,4-dioxo-pyrimidin
5-fluoro-pyrimidine-2,4-diol
GTPL4789
UPCMLD-DP130:001
Fluorouracil (JP18/USP/INN)
HMS500C16
KBio1_000054
KBio2_001321
KBio2_003889
KBio2_006457
KBio3_001268
5-Fluoro-2,3H)-pyrimidinedione
5-FLUOROURACIL [WHO-IP]
L01BC02
2,4-Pyrimidinedione, 5-fluoro-
NINDS_000054
BCPP000428
FLUOROURACIL [ORANGE BOOK]
HMS1920O18
HMS2090I04
HMS2091F19
HMS3259O03
HMS3261L13
HMS3654K22
HMS3715H03
HMS3865L03
Pharmakon1600-01500305
5-Fluorouracil, analytical standard
BCP02083
TCA94195
2,3H)-Pyrimidinedione, 5-fluoro-
5-Fluorouracil - Bio-X trade mark
Fluorouracil (5-Fluoracil, 5-FU)
Fluorouracil (5-Fluoracil; 5-FU)
Tox21_110150
Tox21_202335
Tox21_300112
Tox21_500536
BDBM50340677
CCG-39879
DL-399
HY-90006R
NSC757036
NSC816997
s1209
STK297802
STL367375
FLUOROURACILUM [WHO-IP LATIN]
AKOS000119162
AKOS003237897
AKOS008044307
Tox21_110150_1
BCP9000239
CS-0993
DB00544
FF05372
KS-5129
LP00536
NC00454
NSC-757036
NSC-816997
SDCCGSBI-0050519.P005
FLUCYTOSINE IMPURITY A [WHO-IP]
IDI1_000054
NCGC00015442-01
NCGC00015442-03
NCGC00015442-04
NCGC00015442-05
NCGC00015442-06
NCGC00015442-07
NCGC00015442-08
NCGC00015442-09
NCGC00015442-10
NCGC00015442-11
NCGC00015442-12
NCGC00015442-15
NCGC00015442-16
NCGC00015442-24
NCGC00015442-30
NCGC00091349-01
NCGC00091349-02
NCGC00091349-03
NCGC00091349-04
NCGC00091349-05
NCGC00091349-07
NCGC00091349-08
NCGC00254023-01
NCGC00259884-01
NCGC00261221-01
5-Fluoro-2,4(1H, 3H)-pyrimidinedione
5-Fluoropyrimidine-2,4-(1H,3H)-dione
AC-11201
BF166014
EMTRICITABINE IMPURITY F [WHO-IP]
HY-90006
NCI60_001652
SRI-10792-04
SRI-10792-05
SRI-10792-06
SRI-10792_07
SRI-10792_08
5-Fluoro-1H-pyrimidine-2,4-dione(5FU)
5-Fluorouracil, >=99% (HPLC), powder
SBI-0050519.P004
2(1H)-Pyrimidinone, 5-fluoro-4-hydroxy-
4(3H)-Pyrimidinone, 5-fluoro-2-hydroxy-
5-Fluoro-1H-pyrimidine-2,4-dione(5-FU)
DB-051923
DB-065735
DB-268958
DB-272209
DB-297613
pyrimidine-2,4(1H,3H)-dione, 5-fluoro-
5-Fluoro-1H-pyrimidine-2,4-dione (5-FU)
EU-0100536
NS00000337
SW199617-3
5-Fluoro-1H-pyrimidine-2,4-dione(5-FUra)
5-FLUOROPYRIMIDIN-2,4(1H,3H)-DIONE
EN300-33909
Fluorouracil, meets USP testing specifications
C07649
D00584
5-Fluorouracil, Vetec(TM) reagent grade, >=99%
Q238512
W-60379
(5-fluorouracil)5-Fluoro-1H-pyrimidine-2,4-dione
5-Fluoro-1H-pyrimidine-2,4-dione(5-fluoro uracil)
SR-01000075881-1
SR-01000075881-3
SR-01000075881-5
5-Fluoro-1H-pyrimidine-2,4-dione (5-Fluorouracil)
BRD-K24844714-001-02-1
BRD-K24844714-001-24-5
BRD-K24844714-001-25-2
5-FLUOROPYRIMIDIN-2,4(1H,3H)-DIONE [WHO-IP]
Z275128052
5-Fluoro-1H-pyrimidine-2,4-dione(5-fluorouracil)(5-FU)
5-Fluorouracil, certified reference material, TraceCERT(R)
Fluorouracil, British Pharmacopoeia (BP) Reference Standard
Fluorouracil, European Pharmacopoeia (EP) Reference Standard
Fluorouracil, United States Pharmacopeia (USP) Reference Standard
pyrimidine antimetabolite: inhibits nucleic acid replication; tetratogen
2,4-Dihydroxy-5-fluoropyrimidine;5-FU;5-Fluoro-2,4(1H,3H)-pyrimidinedione
5FU;5-FU;2,4-Dihydroxy-5-fluoropyrimidine;5-Fluoro-2,4(1H,3H)-pyrimidinedione
Fluorouracil, Pharmaceutical Secondary Standard; Certified Reference Material
InChI=1/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9
200-085-6