2'-Deoxy-2'-fluorocytidine supplier

Name
4-Amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
EINECS 233-515-6
CAS No. 10212-20-1
Article Data30
CAS DataBase
Density 1.82 g/cm³
Solubility
Melting Point 167 °C
Formula C₉H₁₂FN₃O₄
Boiling Point 500.1 °C at 760 mmHg
Molecular Weight 245.21
Flash Point 256.2 °C
Transport Information
Appearance White or almost white crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms UNII-LCY080JPY9;4-Amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;2'-Fluoro-2'-deoxy-b-D-ribofuranosylcytosine;2'-Fluoro-2'-deoxycytidine;NSC 529432;
PSA 110.60000
LogP -1.00460

Synthetic route

: 157024-78-7
9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>cytosine

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
With ethanol; pyridinium p-toluenesulfonate for 24h; Heating;	66%

: 3',5'-Di-O-benzoyl-2'-desoxy-2'-fluorcytidin

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
With ammonium hydroxide at 50℃;	56%

: Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-tetrahydro-furan-3-yl ester

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
With N,N-dimethyl-ethanamine In methanol at 50℃; for 24h; Yield given;

: 31698-14-3
cyclocitidine

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
With potassium fluoride

: 10212-13-2
3’,5’-O-acetyl-2’-deoxy-2’-fluorouridine

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: (PhO)2POCl, Et3N / acetonitrile / 1.5 h / Ambient temperature 2: 32percent aq. NH3 / dioxane / 0.33 h 3: EtNMe2 / methanol / 24 h / 50 °C View Scheme

: 56287-17-3, 69123-94-0, 784-71-4
2'-deoxy-2'-fluorouridine

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / pyridine / 2 h / Ambient temperature 2: (PhO)2POCl, Et3N / acetonitrile / 1.5 h / Ambient temperature 3: 32percent aq. NH3 / dioxane / 0.33 h 4: EtNMe2 / methanol / 24 h / 50 °C View Scheme

: 196928-90-2
Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-4-fluoro-5-[4-(3-nitro-[1,2,4]triazol-1-yl)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 32percent aq. NH3 / dioxane / 0.33 h 2: EtNMe2 / methanol / 24 h / 50 °C View Scheme

: 3736-77-4
2,2'-Anhydrouridine

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / p-TsOH / dimethylformamide / 2.5 h / 0 °C 2: 25.1 g / 1 N aq. NaOH / methanol / 1.5 h / Ambient temperature 3: 57 percent / diethylaminosulfur trifluoride (DAST), pyridine / CH2Cl2 / 3 h / Heating 4: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d 5: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating View Scheme

Yield

Multi-step reaction with 5 steps
1: 87 percent / p-TsOH / dimethylformamide / 2.5 h / 0 °C
2: 25.1 g / 1 N aq. NaOH / methanol / 1.5 h / Ambient temperature
3: 57 percent / diethylaminosulfur trifluoride (DAST), pyridine / CH2Cl2 / 3 h / Heating
4: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d
5: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating
View Scheme

: 351523-07-4
3',5'-di-O-(tetrahydropyran-2-yl)-2,2'-O-cyclouridine

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 25.1 g / 1 N aq. NaOH / methanol / 1.5 h / Ambient temperature 2: 57 percent / diethylaminosulfur trifluoride (DAST), pyridine / CH2Cl2 / 3 h / Heating 3: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d 4: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating View Scheme

Yield

Multi-step reaction with 4 steps
1: 25.1 g / 1 N aq. NaOH / methanol / 1.5 h / Ambient temperature
2: 57 percent / diethylaminosulfur trifluoride (DAST), pyridine / CH2Cl2 / 3 h / Heating
3: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d
4: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating
View Scheme

: 157024-75-4
9-<3,5-di-O-(tetrahydropyran-2-yl)-β-D-arabinofuranosyl>uracil

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 57 percent / diethylaminosulfur trifluoride (DAST), pyridine / CH2Cl2 / 3 h / Heating 2: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d 3: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating View Scheme

: 157024-77-6
9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>uracil

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) 4-chlorophenyl phosphorodichloridate, 1,2,4-triazole, pyridine, 2.) conc. NH4OH / 1.) RT, 2 d, 2.) dioxane, RT, 1 d 2: 66 percent / pyridinium p-toluenesulfonate (PPTS), C2H5OH / 24 h / Heating View Scheme

: 3',5'-Di-o-benzoyl-2'-desoxy-2'-fluoruridin

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 73 percent / p-Cl-C6H4-OP(O)Cl2 2: 82 percent / conc. aq. NH3 / dioxane / 1 h 3: 56 percent / conc. NH3 / 50 °C View Scheme

: 128963-08-6
4-Tetrazolo-3',5'-di-O-benzoyl-2'-fluor-1(2H)-pyrimidinon

: 10212-20-1
2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / conc. aq. NH3 / dioxane / 1 h 2: 56 percent / conc. NH3 / 50 °C View Scheme

: 93-97-0
benzoic acid anhydride

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 146954-76-9
N4-benzoyl-2-deoxy-2-fluorocytidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	100%
In N,N-dimethyl-formamide at 20℃;	100%
In N,N-dimethyl-formamide	92%

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 5-bromo-2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
With pyridine; bromine In tetrachloromethane at 20℃; for 0.416667h;	84%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 1246253-27-9
2'-deoxy-2'-fluoro-5'-O-TBDMS-cytidine

Conditions

Conditions	Yield
With pyridine at 20℃;	82%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h; regioselective reaction;	77%
With pyridine at 20℃; for 16h; Cooling with ice;
With pyridine

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 80791-93-1
5-iodo-2'-deoxy-2'-(R)-fluoro-cytidine

Conditions

Conditions	Yield
With iodine; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl-formamide at 20℃; for 7h;	67%
With Iodine monochloride In methanol at 50℃; for 4h;	39%
With iodine; iodic acid; acetic acid In tetrachloromethane; water at 45℃; for 4h; Iodination;

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 2'-deoxy-2'-fluoro-N4-hydroxycytidine

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In water at 55℃; for 16h; pH=5; Inert atmosphere;	47%
With hydroxylamine hydrochloride In water at 55℃; for 16h; pH=5; Sealed tube; Inert atmosphere;	91 mg

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 5-chloro-2'-deoxy-2'-fluorocytidine

Conditions

Conditions	Yield
With benzoyl chloride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl-formamide at 20℃; for 0.5h;	24%

: 75-36-5
acetyl chloride

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-tetrahydro-furan-3-yl ester; hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride at 90 - 95℃; for 0.5h;

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 1904-98-9
2,6-diaminopurine

: 134444-47-6
2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine

Conditions

Conditions	Yield
With E. coli BMT-4D Substitution;

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: N-{3-[4-Amino-1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HIO3; I2; AcOH / CCl4; H2O / 4 h / 45 °C 2: CuI; (Ph3P)4P; Et3N / dimethylformamide / 16 h View Scheme

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 78842-13-4
2'-deoxy-2'-fluoroguanosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: E. coli BMT-4D/1A 2: ADase View Scheme

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 146954-77-0
N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-fluoro-2'-deoxycytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / dimethylformamide 2: 87 percent / Et3N / pyridine View Scheme

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 161442-19-9
N4-benzoyl-2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(β-cyanoethyl N,N-diisopropylphosphoramidite)

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / dimethylformamide 2: 87 percent / Et3N / pyridine 3: 90 percent / (i-Pr)2EtN / CH2Cl2 View Scheme

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 83966-99-8
3',5'-di-O-acetyl-2'-deoxy-2'-fluoro-5-iodocytosine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) HCl / 0.5 h / 90 - 95 °C 2: I2, HIO3, AcOH / H2O; CCl4 / 24 h / 50 - 55 °C View Scheme

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 146954-76-9
N4-benzoyl-2-deoxy-2-fluorocytidine

: 10212-20-1
2'-deoxy-2'-fluorocytidine

: 58479-61-1
tert-butylchlorodiphenylsilane

: C25H30FN3O4Si

Conditions

Conditions	Yield
With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 50℃; for 12h;

2'-Deoxy-2'-fluorocytidine Specification

The 2'-Deoxy-2'-fluorocytidine, with the CAS registry number 10212-20-1, is also known as 2'-Fluoro-2'-deoxycytidine. It belongs to the product categories of Biochemistry; Nucleosides and Their Analogs; Nucleosides, Nucleotides & Related Reagents. This chemical's molecular formula is C₉H₁₂FN₃O₄ and molecular weight is 245.21. Its IUPAC name is called . The product should be sealed and stored in cool, dry place.

Physical properties of 2'-Deoxy-2'-fluorocytidine: (1)ACD/LogP: -1.26; (2)ACD/LogD (pH 5.5): -1.26; (3)ACD/LogD (pH 7.4): -1.26; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 4.9; (7)ACD/KOC (pH 7.4): 4.91; (8)#H bond acceptors: 7; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.697; (12)Molar Refractivity: 51.66 cm³; (13)Molar Volume: 134 cm³; (14)Surface Tension: 71.3 dyne/cm; (15)Density: 1.82 g/cm³; (16)Flash Point: 256.2 °C; (17)Enthalpy of Vaporization: 88.51 kJ/mol; (18)Boiling Point: 500.1 °C at 760 mmHg; (19)Vapour Pressure: 4.27E-12 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)F
(2)Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)F
(3)InChI: InChI=1S/C9H12FN3O4/c10-6-7(15)4(3-14)17-8(6)13-2-1-5(11)12-9(13)16/h1-2,4,6-8,14-15H,3H2,(H2,11,12,16)/t4-,6-,7-,8-/m1/s1
(4)InChIKey: NVZFZMCNALTPBY-XVFCMESISA-N

Product Name

4-Amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

Synthetic route

2'-Deoxy-2'-fluorocytidine Specification

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