2',2'-Difluoro-2'-deoxyuridine

Modify Date: 2025-08-23 16:43:08

2',2'-Difluoro-2'-deoxyuridine Structure
2',2'-Difluoro-2'-deoxyuridine structure
 Common Name 2',2'-Difluoro-2'-deoxyuridine
CAS Number 114248-23-6 Molecular Weight 264.183
Density 1.7±0.1 g/cm3 Boiling Point N/A
Molecular Formula C9H10F2N2O5 Melting Point 147-149ºC
MSDS N/A Flash Point N/A

 Use of 2',2'-Difluoro-2'-deoxyuridine


2′,2′-Difluorodeoxyuridine (dFdU) is the main metabolite of Gemcitabine (HY-17026). 2′,2′-Difluorodeoxyuridine causes a concentration- and schedule- dependent radiosensitising effect in vitro[1].

 Names

Name 2',2'-Difluoro-2'-deoxyuridine
Synonym More Synonyms

 2',2'-Difluoro-2'-deoxyuridine Biological Activity

Description 2′,2′-Difluorodeoxyuridine (dFdU) is the main metabolite of Gemcitabine (HY-17026). 2′,2′-Difluorodeoxyuridine causes a concentration- and schedule- dependent radiosensitising effect in vitro[1].
Related Catalog
References

[1]. Pauwels B, et al. The radiosensitising effect of difluorodeoxyuridine, a metabolite of gemcitabine, in vitro. Cancer Chemother Pharmacol. 2006 Aug;58(2):219-28.  

 Chemical & Physical Properties

Density 1.7±0.1 g/cm3
Melting Point 147-149ºC
Molecular Formula C9H10F2N2O5
Molecular Weight 264.183
Exact Mass 264.055786
PSA 104.55000
LogP -0.53
Index of Refraction 1.587
InChIKey FIRDBEQIJQERSE-QPPQHZFASA-N
SMILES O=c1ccn(C2OC(CO)C(O)C2(F)F)c(=O)[nH]1
Storage condition -20°C Freezer

 Synthetic Route

2′,2′-Difluoro-2′-deoxyuridine 3′,5′-Dibenzoate structure

2′,2′-Difluoro-...

CAS#:143157-27-1

~94%

2',2'-Difluoro-2'-deoxyuridine Structure

2',2'-Difluoro-...

CAS#:114248-23-6

Literature: ALIOS BIOPHARMA, INC.; Beigelman, Leonid; Wang, Guangyi; Smith, David Bernard; Deval, Jerome; Prhavc, Marija Patent: US2013/165400 A1, 2013 ; Location in patent: Paragraph 0420; 0421 ;
2'-deoxy-2',2'-difluorouridine-3',5'-dibenzoate structure

2'-deoxy-2',2'-...

CAS#:1201895-94-4

~91%

2',2'-Difluoro-2'-deoxyuridine Structure

2',2'-Difluoro-...

CAS#:114248-23-6

Literature: Chou; Heath; Patterson; Poteet; Lakin; Hunt Synthesis, 1992 , # 6 p. 565 - 570
Gemcitabine HCl structure

Gemcitabine HCl

CAS#:122111-03-9

~%

2',2'-Difluoro-2'-deoxyuridine Structure

2',2'-Difluoro-...

CAS#:114248-23-6

Literature: US2013/165400 A1, ;
(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate structure

(2R,3R,5R)-5-(4...

CAS#:1445381-44-1

~%

2',2'-Difluoro-2'-deoxyuridine Structure

2',2'-Difluoro-...

CAS#:114248-23-6

Literature: US2013/165400 A1, ;
gemcitabine structure

gemcitabine

CAS#:103882-84-4

~%

2',2'-Difluoro-2'-deoxyuridine Structure

2',2'-Difluoro-...

CAS#:114248-23-6

Literature: Journal of Organic Chemistry, , vol. 53, # 11 p. 2406 - 2409

 Synonyms

2(1H)-Pyrimidinone, 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)-4-hydroxy-
1-(2-Deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)-4-hydroxy-2(1H)-pyrimidinone
Uridine, 2'-deoxy-2',2'-difluoro-
Gemcitabine impurity C
2',2'-Difluoro-2'-deoxyuridine
2′,2′-difluorodeoxyuridine
2'-Deoxy-2',2'-difluorouridine
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