ChemicalBook > CAS DataBase List > 2',2'-DIFLUORO-2'-DEOXYURIDINE

2',2'-DIFLUORO-2'-DEOXYURIDINE

Product Name
2',2'-DIFLUORO-2'-DEOXYURIDINE
CAS No.
114248-23-6
Chemical Name
2',2'-DIFLUORO-2'-DEOXYURIDINE
Synonyms
Gemcitabine impurity C;Gemcitabine Metabolite;2Deoxy-22difluorouridine;2',2'-Difluorodeoxyuridine;1-((2R,4R,5R)-3,3-difluoro;Gemcitabine Dione Impurity;Gemcitabine Impurity C (EP);2',2'-DIFLUORO-2'-DEOXYURIDINE;2'-Deoxy-2',2'-difluorouridine;Uridine,2'-deoxy-2',2'-difluoro-
CBNumber
CB5209925
Molecular Formula
C9H10F2N2O5
Formula Weight
264.18
MOL File
114248-23-6.mol
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2',2'-DIFLUORO-2'-DEOXYURIDINE Property

Melting point:
147-149°C
Density 
1.69±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
solubility 
Methanol (Slightly), Water (Very Slightly, Heated)
form 
Solid
pka
9.39±0.10(Predicted)
color 
White to Off-White
InChI
InChI=1S/C9H10F2N2O5/c10-9(11)6(16)4(3-14)18-7(9)13-2-1-5(15)12-8(13)17/h1-2,4,6-7,14,16H,3H2,(H,12,15,17)/t4-,6-,7-/m1/s1
InChIKey
FIRDBEQIJQERSE-PRMYIZFSSA-N
SMILES
OC[C@H]1O[C@@H](N2C=CC(=O)NC2=O)[C@](F)(F)[C@@H]1O
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Safety

HS Code 
29389090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0001682
Product name
Gemcitabine impurity C
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
25 mg
Price
$236
Updated
2025/07/31
Sigma-Aldrich
Product number
Y0001682
Product name
Gemcitabine impurity C
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0001682
Price
$220
Updated
2024/03/01
TRC
Product number
D445740
Product name
2’,2’-Difluoro-2’-deoxyuridine
Packaging
1mg
Price
$45
Updated
2021/12/16
TRC
Product number
D445740
Product name
2’,2’-Difluoro-2’-deoxyuridine
Packaging
10mg
Price
$245
Updated
2021/12/16
Biosynth Carbosynth
Product number
ND06954
Product name
2'-Deoxy-2',2'-difluorouridine
Packaging
50mg
Price
$350
Updated
2021/12/16
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2',2'-DIFLUORO-2'-DEOXYURIDINE Chemical Properties,Usage,Production

Chemical Properties

Off-White Solid

Uses

A metabolite product of Gemcitabine

Uses

A metabolite of Gemcitabine (G305000) in human plasma.

Definition

ChEBI: 2',2'-Difluorodeoxyuridine is a pyrimidine 2'-deoxyribonucleoside.

Synthesis

122111-03-9

114248-23-6

General procedure for the synthesis of 1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one hydrochloride from 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2,4(1H,3H)-dione As follows: 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one hydrochloride (5 g, 16.7 mmol, 1.0 eq.) was dissolved in 2N aqueous acetic acid (350 ml), sodium nitrite (16.7 g, 14.5 eq.) was added slowly and the reaction mixture The reaction mixture was allowed to stand at room temperature for 48 hours. Subsequently, the pH of the reaction mixture was adjusted to 6-7 with 2N aqueous sodium hydroxide and concentrated under reduced pressure. To the concentrated residue, a solvent mixture of methanol/ethyl acetate (1:5, 360 ml) was added and the insoluble salt was removed by filtration. This operation was repeated several times to remove the salt completely, and finally the filtrate was concentrated under reduced pressure to give 4.22 g of the target product 1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione as a light brown transparent oil in 95% yield.

References

[1] Patent: KR101794970, 2017, B1. Location in patent: Paragraph 0095-0097
[2] Patent: US2013/165400, 2013, A1
[3] Patent: WO2014/209979, 2014, A1
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 4, p. 1862 - 1878
[5] Patent: US2015/105341, 2015, A1

2',2'-DIFLUORO-2'-DEOXYURIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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2',2'-DIFLUORO-2'-DEOXYURIDINE Suppliers

Canada 2 China 130 China Hong Kong 1 France 1 Germany 1 India 5 Switzerland 2 United Kingdom 5 United States 10 Global 157
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View Lastest Price from 2',2'-DIFLUORO-2'-DEOXYURIDINE manufacturers

Shenzhen Nexcon Pharmatechs Ltd.
Product
2',2'-DIFLUORO-2'-DEOXYURIDINE 114248-23-6
Price
US $0.00-0.00/G
Min. Order
1G
Purity
97%
Supply Ability
2000
Release date
2025-05-30
Hong Kong Tiansheng New Material Trading Co., Ltd
Product
2',2'-Difluoro-2'-deoxyuridine 114248-23-6
Price
US $1.99/KG
Min. Order
1KG
Purity
99%
Supply Ability
3tons
Release date
2021-12-08
Career Henan Chemical Co
Product
2',2'-DIFLUORO-2'-DEOXYURIDINE 114248-23-6
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000KG
Release date
2018-08-13

114248-23-6, 2',2'-DIFLUORO-2'-DEOXYURIDINERelated Search:

Uridine Diphosphate Choline UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT Tetrahydrouridine 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione [[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy URIDINE 5'-DIPHOSPHOGLUCOSE DISODIUM SALT 1-(-D-Xylofuranosyl)uracil Uridine Diphosphate Choline (UDPC) Sodium Salt alpha-D-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) 2,4(1H,3H)-Pyrimidinedione, 5-[5-O-[hydroxy(phosphonooxy)phosphinyl]-β-D-ribofuranosyl]- [5-(2,4-dioxo-1H-pyrimidin-5-yl)-3,4-dihydroxy-oxolan-2-yl]methoxyphosphonic acid 2,4(1H,3H)-Pyrimidinedione, 5-[5-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-ribofuranosyl]- Deoxyribonucleoside 2'-Fluoro-2'-deoxyuridine 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil 2',2'-DIFLUORO-2'-DEOXYURIDINE 13C, 15N2 2',2'-DIFLUORO-2'-DEOXYURIDINE 2'',2''-DIFLUORO-2''-DEOXYURIDINE (DFDU)

  • 2',2'-DIFLUORO-2'-DEOXYURIDINE
  • 2'-Deoxy-2',2'-difluoro-D-uridine
  • 2',2'-Difluorodeoxyuridine
  • 2Deoxy-22difluorouridine
  • 2'-deoxy-2',2'-fluorouracil nucleoside
  • 2'-Deoxy-2',2'-difluorouridine ,97%
  • Gemcitabine Metabolite
  • Uridine,2'-deoxy-2',2'-difluoro-
  • Gemcitabine impurity C
  • 1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  • 2',2'-DIFLUORO-2'-DEOXYURIDINE(Gemcitabine impurity)
  • Gemcitabine impurity 6/2',2'-Difluoro-2'-Deoxy Uridine
  • Uridine Impurity 4 (2',2'-Difluoro-2'-Deoxy Uridine）
  • 1-((2R,4R,5R)-3,3-difluoro
  • Gemcitabine Impurity C (EP)
  • Gemcitabine Dione Impurity
  • 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin- 2,4(1H,3H)-dione (2′-deoxy-2′,2′-difluorouridine)
  • 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2,4(1H,3H)-dione (2′-deoxy-2′,2′-difluorouridine) (β-uridine)
  • 1-[(2R,4R,5R)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)-2-tetrahydrofuryl]pyrimidine-2,4(1H,3H)-dione
  • 2'-Deoxy-2',2'-difluorouridine
  • dFdU|||2',2'-Difluoro-2'-deoxyuridine
  • 1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
  • Uridine, 2'-deoxy-2',2'-difluoro-
  • 1-(2-Deoxy-2,2-difluoro-beta-D-erythro-pentofuranosyl)pyrimidin-2,4(1H,3H)-dione (2'-Deoxy-2',2'-dif
  • 2'-deoxy-2',2'-difluorouridine 97%
  • 1-(2-Deoxy-2,2-difluoro-beta-D-erythro-pentofuranosyl)pyrimidin-2,4(1H,3H)-dione (2'-Deoxy-2',2'-difluorouridine)
  • 114248-23-6
  • C9H10F2N2O5
  • Carbohydrates & Derivatives
  • Heterocycles
  • Nucleotides
  • Bases & Related Reagents
  • Metabolites & Impurities