5-Fluorouridine

Basic Information

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CAS Number

316-46-1

Molecular Formula

C9H11FN2O6

Molecular Weight

262.19 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Specialty Chemicals UV Stabilizers

Agricultural Chemicals Pesticides Herbicides

Basic Physical Properties

Physical State

White to Yellow Solid

Melting Point

185°C

Refractive Index

18 ° (C=1, H2O)

Specific Rotation

17 º (c=2, water 25 ºC)

SMILES

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C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)F

InChI

InChI=1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1

InChIKey

FHIDNBAQOFJWCA-UAKXSSHOSA-N

LogP

-2.712799999999999

Topological Polar Surface Area

124.78 Å²

Hydrogen Bond Donor/Acceptor

4 / 8

Complexity

414

Safety Information

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Hazard Statement

H341 Suspected of causing genetic defects
Germ cell mutagenicity

H373 Causes damage to organs through prolonged or repeated exposure
Specific target organ toxicity, repeated exposure

Synonyms & References

English

SCHEMBL53091
4pb2
5-FLUOROURACIL-1.BETA.-D-RIBOFURANOSIDE
Uridine, 5-fluoro-
5-Fur
AKOS015852922
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidine-2,4-dione
BRN 0033662
NCGC00142485-02
AFU
DB01629
5-Fluorouracil 1-.beta.-D-arabinosyl
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione
PD008907
C9H11FN2O6
NSC 146604
2,4(1H,3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-fluoro-
1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione
1-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,3-dihy dropyrimidine-2,4-dione
CHEMBL54918
FUrd
BDBM50132299
beta-D-5FdU
5-Fluoro-1-.beta.-D-ribofuranosyluracil
cid_1821
5-Fluorouridine
5-Fluorouridine, >=99.0% (HPLC)
CHEBI:40154
5UD
J-700089
1-((2R,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione

MDL Number

MFCD00036832

Customs Code

2942000000

FAQ

What are the physical and chemical properties of 5-Fluorouridine (CAS: 316-46-1)?

5-Fluorouridine is a white crystalline powder with a molecular weight of 188.03 g/mol. It is soluble in ethanol, methanol, and water, but less so in organic solvents like chloroform. Chemically, it is a nucleoside derivative with good reactivity towards nucleophilic substitution reactions, making it a key intermediate in the synthesis of antiviral and anticancer drugs.

How is 5-Fluorouridine (CAS: 316-46-1) typically synthesized?

5-Fluorouridine is commonly synthesized through the reaction of 5-fluorouracil with uridine-5'-monophosphate (UMP) in the presence of a suitable catalyst such as sodium hydride. The process involves nucleophilic substitution and yields 5-fluorouridine with good selectivity and moderate yield, making it an efficient method for large-scale production.

What industries use 5-Fluorouridine (CAS: 316-46-1)?

5-Fluorouridine is primarily used in the pharmaceutical industry as an intermediate for the production of anti-cancer drugs, particularly fluorouracil (5-FU). It is also of interest in research for its potential applications in nucleic acid chemistry and biochemistry.

What precautions should be taken when handling 5-Fluorouridine (CAS: 316-46-1)?

When handling 5-Fluorouridine, it is important to use appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. Ensure that work is conducted in a well-ventilated area or a fume hood to prevent inhalation or skin contact. In case of spills, evacuate the area and clean up using appropriate chemicals. Always refer to the safety data sheet (SDS) for detailed handling and emergency procedures.