Name: 2'-Deoxyuridine
SKU: 951-78-0

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Basic Information

Molecular Structure:
CAS No.:	951-78-0
Name:	2'-Deoxyuridine

Formula:	C₉H₁₂N₂O₅
Molecular Weight:	228.205
Synonyms:	1-(2-Deoxy-b-D-erythro-pentofuranosyl)uracil;2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-b-D-erythro-pentofuranosyl)-;2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-b-D-ribofuranosyl)-;2'-Desoxyuridine;Deoxyribose uracil;Deoxyuridine;NSC 23615;Uracildeoxyriboside;1-(2-Deoxy-b-D-ribofuranosyl)uracil;1-(2-Deoxy-D-erythro-pentofuranosyl)uracil;Uridine, 2'-deoxy-;
EINECS:	213-455-7
Density:	1.533 g/cm³
Melting Point:	167-169 °C(lit.)
Boiling Point:	370.01°C (rough estimate)
Solubility:	300 g/L at 20°C in water
Appearance:	White crystalline powder
Hazard Symbols:	Xn
Risk Codes:	36/37/38
Safety:	22-24/25-37/39
PSA:	104.55000
LogP:	-1.82270

Synthetic route

: 14270-73-6
O5'-trityl-2'-deoxy-uridine

: 951-78-0
2'-deoxyuridine

Conditions

Conditions	Yield
With silica gel; trifluoroacetic acid In methanol; chloroform	100%

: 951-77-9
2'-Deoxycytidine

: 951-78-0
2'-deoxyuridine

Conditions

Conditions	Yield
With cytidine deaminase enzyme In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7; Enzymatic reaction;	99%
With acetic acid; sodium nitrite
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration, decomposition to nonchromophoric products;

: 130197-82-9
4-O-(2,4,6-Trimethylphenyl)-2'-deoxyuridine

A: 951-78-0
2'-deoxyuridine

B: 951-77-9
2'-Deoxycytidine

Conditions

Conditions	Yield
With ammonium hydroxide at 65℃; for 2h;	A n/a B 98%

: 59-14-3
5-bromo-2'-deoxyuridine

: 951-78-0
2'-deoxyuridine

Conditions

Conditions	Yield
With triethylamine In methanol; water at 4℃; for 12h; Irradiation; sensitizer: methylene blue;	96%
Multi-step reaction with 3 steps 1: 99.7 percent / p-toluenesulfonic acid / tetrahydrofuran / 2 h / Ambient temperature 2: n-BuLi, MeI / tetrahydrofuran; hexane / -78 °C 3: 1N HCl / methanol / 0.08 h / Heating View Scheme
Multi-step reaction with 2 steps 1: (NH4)2SO4 / Heating 2: 1) PdCl3, Ph3P, 2) NH4Cl, H2O / 1) THF, reflux, 12 h, 2) MeOH, reflux, 3 h View Scheme
With sodium tetrahydroborate; Naphthalene-1,8-diselenol In aq. phosphate buffer at 37℃; pH=7; Reagent/catalyst;
With sodium tetrahydroborate; C10H8Te In aq. phosphate buffer at 37℃; pH=7; Kinetics; Reagent/catalyst;

: 64911-18-8
3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine

: 951-78-0
2'-deoxyuridine

Conditions

Conditions	Yield
With K 10 clay In methanol; water at 75℃; for 12h;	94%

: 98495-56-8
3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine

: 951-78-0
2'-deoxyuridine

Conditions

Conditions	Yield
With K 10 clay In methanol; water at 75℃; for 60h;	90%
With tetrabutyl ammonium fluoride Yield given;

: 66-22-8
uracil

: 7-methyl-2′-deoxyguanosine hydroiodide

: 951-78-0
2'-deoxyuridine

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; Escherichia coli thymidine phosphorylase; Escherichia coli purine nucleoside phosphorylase In aq. buffer at 20℃; for 20h; pH=7.5; Enzymatic reaction;	80%

: 629-45-8
dibutyl disulfide

: 65505-76-2
C5-chloromercuri-2'-deoxyuridine

A: 951-78-0
2'-deoxyuridine

B: 21740-34-1
5-(1-Thiapentyl)-2'-deoxyuridine

Conditions

Conditions	Yield
With lithium tetrachloropalladate(II) In methanol for 16h; Ambient temperature;	A n/a B 73%
With lithium tetrachloropalladate(II) In methanol for 16h; Ambient temperature; other organic disulfides;	A n/a B 73%

...Expand

: 1140622-65-6
3'-O-acetyl-5'-O-t-butyldimethylsilyl-2'-deoxyuridine

: 100-51-6
benzyl alcohol

A: 53172-91-1
(benzyloxy)(tert-butyl)dimethylsilane

B: 951-78-0
2'-deoxyuridine

C: 66-22-8
uracil

D: 23197-88-8
3'-O-acetyl-2'-deoxyuridine

Conditions

Conditions	Yield
With copper(II) sulfate In xylene for 2h; Heating;	A n/a B n/a C n/a D 72%

...Expand

: 58-96-8
uridine

: 951-78-0
2'-deoxyuridine

Conditions

Conditions	Yield
Multistep reaction;	60%
Multi-step reaction with 4 steps 1: 90 percent / pyridine / 2 h / Ambient temperature 2: 4-(dimethylamino)pyridine / acetonitrile / 6 h / Ambient temperature 3: tri-n-butylstannane, α,α'-azoisobutyronitrile / toluene / 3 h / 75 °C 4: tetra-n-butylammonium fluoride View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide; bis(phenyl) carbonate / N,N-dimethyl-formamide / 12 h / 140 °C 2: hydrogenchloride / N,N-dimethyl-formamide / 14 h / 40 °C 3: sodium hydroxide; nickel; hydrogen / methanol / 20 h / 40 °C View Scheme

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 2'-Deoxyuridine, with the CAS registry number 951-78-0 and EINECS registry number 213-455-7, has the IUPAC name of 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione. It is a kind of white crystalline powder which is also air sensitive. The molecular formula of the chemical is C₉H₁₂N₂O₅. What's more, while dealing with this chemical, you should not breathe dust and then try to avoid contacting with skin and eyes.

The physical properties of 2'-Deoxyuridine are as followings: (1)ACD/LogP: -1.70; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.7; (4)ACD/LogD (pH 7.4): -1.74; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.82; (8)ACD/KOC (pH 7.4): 2.58; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 68.31 Å²; (13)Index of Refraction: 1.603; (14)Molar Refractivity: 51.14 cm³; (15)Molar Volume: 148.8 cm³; (16)Polarizability: 20.27×10^-24cm³; (17)Surface Tension: 71.1 dyne/cm; (18)Density: 1.533 g/cm³.

Uses of 2'-Deoxyuridine: It is always used as an uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease. And it is also used as intermediates.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Do not breathe dust and avoid contacting with skin and eyes; Wear suitable gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C/1NC(=O)N(\C=C\1)C2O[C@@H]([C@@H](O)C2)CO
(2)InChI: InChI=1/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8?/m0/s1
(3)InChIKey: MXHRCPNRJAMMIM-FWHJPCMOBR

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Consensus Reports

Specification