5'-Deoxy-5-fluorouridine

Basic Information

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CAS Number

3094-09-5

Molecular Formula

C9H11FN2O5

Molecular Weight

246.19 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

Powder

Melting Point

187.0 to 191.0 deg-C

Refractive Index

20 ° (C=1, H2O)

Specific Rotation

+18° - +22° (c=1, H2O)

SMILES

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CC1C(C(C(O1)N2C=C(C(=O)NC2=O)F)O)O

InChI

InChI=1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1

InChIKey

ZWAOHEXOSAUJHY-ZIYNGMLESA-N

LogP

-1.6851999999999996

pKa

7.4(at 25℃)

Topological Polar Surface Area

104.55000000000001 Å²

Hydrogen Bond Donor/Acceptor

3 / 7

Complexity

399

Safety Information

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Hazard Statement

H303 May be harmful if swallowed
Acute toxicity, oral

H316 Causes mild skin irritation
Skin corrosion/irritation

H317 May cause an allergic skin reaction
Sensitization, Skin

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

Hazard Class

Class IRRITANT Class IRRITANT

Class IRRITANT-HARMFUL Class IRRITANT-HARMFUL

Toxicity

LD50 (14 day) in mice or rats (mg/kg): >1000 i.v.: >2000 s.c.; in male, female mice, male, female rats (mg/kg): >5000, >5000, 3471, 3390 orally (Shimizu)

Synonyms & References

English

1-(beta-D-5-Desoxyribofuranoxyl)-5-fluoruracil
Fulturon
NSC-758890
MLS002207077
MLS001332580
5'-Doxifluridine
AMC 0101
CAS-3094-09-5
UNII-V1JK16Y2JP
1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoropyrimidine-2,4(1H,3H)-dione (5'-Deoxy-5-fluorouridine)
SRI-11552_09
doxifluridine
SR-01000075886-5
1-((4S,2R,3R,5R)-3,4-Dihydroxy-5-methyloxolan-2-yl)-5-fluoro-1,3-dihydropyrimidine-2,4-dione
SMR000326811
ZWAOHEXOSAUJHY-ZIYNGMLESA-N
Doxifluridine [INN:JAN]
5-Deoxy-5'-fluorouridine
5-fluoro-5'-deoxyuridine
NS00046999
NCGC00093926-02
5'-dFUrd
5'dFUrd
5''-Deoxy-5-Fluorouridine (5''-Dfur)
NCGC00093926-01
BP-58654
DTXSID2022967
1-((2R,5R)-3,4-Dihydroxy-5-methyl-tetrahydro-furan-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione
Doxifluridine (5-Fluoro-5'-deoxyuridine)
Ro 21-9738
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione

MDL Number

MFCD00866530

Customs Code

2934999090

FAQ

What are the physical and chemical properties of 5'-Deoxy-5-fluorouridine (CAS: 3094-09-5)?

5'-Deoxy-5-fluorouridine (5'-DFUR) is a crystalline compound with a molecular weight of approximately 193.14 g/mol. It has a solubility of about 10 mg/mL in water and is relatively stable in acidic and neutral solutions. However, it is susceptible to hydrolysis in basic conditions. The compound shows limited reactivity towards nucleophilic substitutions and can be used as a fluorinated analog in various chemical reactions.

How is 5'-Deoxy-5-fluorouridine (CAS: 3094-09-5) typically synthesized?

5'-Deoxy-5-fluorouridine (5'-DFUR) is commonly synthesized via the fluoroalkylation of 5'-deoxyuridine. The reaction typically uses fluoride sources like sodium fluoride and is catalyzed by a phase-transfer catalyst. The yield is usually around 70-80%, and the selectivity for the desired product is high. This method allows for the controlled introduction of a fluorine atom into the molecule, making it a valuable intermediate in medicinal chemistry.

What industries use 5'-Deoxy-5-fluorouridine (CAS: 3094-09-5)?

5'-Deoxy-5-fluorouridine (5'-DFUR) is primarily used in the pharmaceutical industry due to its potential antiviral and anticancer properties. It is also studied in academic research for its use as a bioisostere in drug design. Additionally, its chemical structure makes it interesting for applications in polymer science and as a precursor in the synthesis of other fluorinated compounds.

What precautions should be taken when handling 5'-Deoxy-5-fluorouridine (CAS: 3094-09-5)?

When handling 5'-Deoxy-5-fluorouridine (5'-DFUR), it is important to wear appropriate personal protective equipment (PPE) such as gloves and safety goggles. Work should be conducted in a well-ventilated area or a fume hood to minimize exposure. Spills should be cleaned up according to the Material Safety Data Sheet (MSDS) guidelines, and the compound should be stored in a cool, dry place away from direct sunlight. Always refer to the latest SDS for detailed safety information.