(+)-5-Iodo-2'-deoxyuridine supplier

Name
(+)-5-Iodo-2'-deoxyuridine
EINECS 200-207-8
CAS No. 54-42-2
Article Data27
CAS DataBase
Density 2.148 g/cm³
Solubility 1.6 g/L (20 ºC)
Melting Point 194 °C(lit.)
Formula C₉H₁₁IN₂O₅
Boiling Point
Molecular Weight 354.101
Flash Point
Transport Information
Appearance crystalline solid
Safety 53-45-36-22
Risk Codes 45-46-61-40
Molecular Structure
Hazard Symbols T,Xn
Synonyms 1-(2-Deoxy-b-D-ribofuranosyl)-5-iodouracil;2'-Deoxy-5-iodouridine;5-Iodo-2'-deoxyuridine;5-Iodo-2'-desoxyuridine;5-Iododeoxyuridine;5-Iodouracil deoxyriboside;5IUDR;Allergan 211;Dendrid;Emanil;Herpe-Gel;Herpesil;Herpidu;Herplex;IDU;IDUR;IUDR;Idexur;Idoxene;Idoxuridin;Idoxuridine;Idu Oculos;Iducher;Idulea;Iduridin;Iododeoxyuridine;Joddeoxiuridin;Kerecid;NSC 39661;Ophthalmadine;SKF 14287;Stoxil;Stoxip;Synmiol;Virudox;
PSA 104.55000
LogP -1.21810

Synthetic route

: 951-78-0
2'-deoxyuridine

: 54-42-2
5-Iodo-2'-deoxyuridine

Conditions

Conditions	Yield
With iodine; silver nitrate In methanol at 40℃; for 3h;	100%
With iodine; silver nitrate In methanol at 40℃; for 3h;	100%
With sodium azide; Iodine monochloride In acetonitrile at 25℃; for 24h; Product distribution; Mechanism; other uracil nucleosides; other halogenation agents; var. temp. and time;	96%

: 1956-30-5
3',5'-O-diacetyl-5-iodo-2'-deoxyuridine

: 54-42-2
5-Iodo-2'-deoxyuridine

Conditions

Conditions	Yield
With sodium methylate In methanol for 1h; Ambient temperature;	90%
With methanol; sodium methylate at 20℃; for 1h;

: 146629-34-7
5-trimethylstannyl-2'-deoxyuridine

: 54-42-2
5-Iodo-2'-deoxyuridine

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; acetic acid; sodium iodide In chloroform for 0.00416667h; Irradiation;

: C23H17Cl2IN2O7

: 54-42-2
5-Iodo-2'-deoxyuridine

Conditions

Conditions	Yield
With ammonia In methanol at 30℃; for 16h;

: 951-78-0
2'-deoxyuridine

: 696-07-1
5-iodouracil

: 54-42-2
5-Iodo-2'-deoxyuridine

Conditions

Conditions	Yield
at 37℃; for 6h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli, ammonium acetate buffer pH 5.8;

: 696-07-1
5-iodouracil

: 50-89-5
thymidine

A: 54-42-2
5-Iodo-2'-deoxyuridine

B: 65-71-4
thymin

Conditions

Conditions	Yield
With thymidine phosphorylase from Escherichia coli In phosphate buffer at 35℃; for 2h; pH=7.0; Title compound not separated from byproducts;	A 88 % Chromat. B n/a

...Expand

: 13030-62-1
3',5'-di-O-acetyl-2'-deoxyuridine

: 54-42-2
5-Iodo-2'-deoxyuridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / LiI, ceric ammonium nitrate (CAN) / acetonitrile / 1 h / 80 °C / other conditions and reagents investigated 2: 90 percent / 0.1 M NaOMe / methanol / 1 h / Ambient temperature View Scheme

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

: 51592-06-4
1,3,4,6-tetrachloro-3α,6α-diphenyl glycoluril

: 54-42-2
5-Iodo-2'-deoxyuridine

Conditions

Conditions	Yield
With sodium iodide In water

: 951-78-0
2'-deoxyuridine

: 696-07-1
5-iodouracil

A: 54-42-2
5-Iodo-2'-deoxyuridine

B: 66-22-8
uracil

Conditions

Conditions	Yield
With thymidine phosphorylase from Escherichia coli (E.C. 2.4.2.4) immobilized on Sepabeads EC-EP In aq. phosphate buffer at 20℃; for 3h; pH=7.5; Reagent/catalyst; Enzymatic reaction;

...Expand

: 13030-62-1
3',5'-di-O-acetyl-2'-deoxyuridine

A: 54-42-2
5-Iodo-2'-deoxyuridine

B: C9H11IN2O5S

C: C18H20I2N4O8S2

D: C18H21IN4O8S2

E: 5580-20-1
2'-deoxy-4-thiouridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: ammonium cerium (IV) nitrate; iodine / acetonitrile / 1 h / 80 °C 2: tetraphosphorus decasulfide / 1,4-dioxane / Reflux 3: sodium hydride / methanol / 0.17 h / 0 - 20 °C 4: aq. phosphate buffer; tert-butyl alcohol / Radiolysis View Scheme

...Expand

: 1956-30-5
3',5'-O-diacetyl-5-iodo-2'-deoxyuridine

A: 54-42-2
5-Iodo-2'-deoxyuridine

B: C9H11IN2O5S

C: C18H20I2N4O8S2

D: C18H21IN4O8S2

E: 5580-20-1
2'-deoxy-4-thiouridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetraphosphorus decasulfide / 1,4-dioxane / Reflux 2: sodium hydride / methanol / 0.17 h / 0 - 20 °C 3: aq. phosphate buffer; tert-butyl alcohol / Radiolysis View Scheme

...Expand

: 1313407-40-7
5-iodo-4-thio-2'-deoxyuridine

A: 54-42-2
5-Iodo-2'-deoxyuridine

B: C9H11IN2O5S

C: C18H20I2N4O8S2

D: C18H21IN4O8S2

E: 5580-20-1
2'-deoxy-4-thiouridine

Conditions

Conditions	Yield
In aq. phosphate buffer; tert-butyl alcohol Radiolysis;

...Expand

: 951-78-0
2'-deoxyuridine

A: 54-42-2
5-Iodo-2'-deoxyuridine

B: C9H11IN2O5S

C: C18H20I2N4O8S2

D: C18H21IN4O8S2

E: 5580-20-1
2'-deoxy-4-thiouridine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / 24 h / 20 °C 2: ammonium cerium (IV) nitrate; iodine / acetonitrile / 1 h / 80 °C 3: tetraphosphorus decasulfide / 1,4-dioxane / Reflux 4: sodium hydride / methanol / 0.17 h / 0 - 20 °C 5: aq. phosphate buffer; tert-butyl alcohol / Radiolysis View Scheme

...Expand

: 696-07-1
5-iodouracil

: 50-89-5
thymidine

: 54-42-2
5-Iodo-2'-deoxyuridine

Conditions

Conditions	Yield
With recobinant purine nucleoside phosphorylase from Escherichia coli In aq. phosphate buffer pH=6.8; Heating; Enzymatic reaction;

: C5H9O7P(2-)*2K(1+)

: 696-07-1
5-iodouracil

: 54-42-2
5-Iodo-2'-deoxyuridine

Conditions

Conditions	Yield
With E-pyrimidine nucleoside phosphorylase-0002 In aq. buffer at 50℃; for 2h; pH=9; Equilibrium constant; Enzymatic reaction;

: 54-42-2
5-Iodo-2'-deoxyuridine

: 292638-85-8
acrylic acid methyl ester

: 86163-17-9
methyl (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate

Conditions

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine In 1,4-dioxane for 14h; Heating;	100%
Stage #1: 5-Iodo-2'-deoxyuridine With C26H32N8O6P2PdS2 In acetonitrile at 80℃; for 0.0833333h; Heck Reaction; Inert atmosphere; Stage #2: acrylic acid methyl ester With triethylamine In acetonitrile at 80℃; for 8h; Heck Reaction; Inert atmosphere;	92%
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 1h;	87%

: 80755-88-0
9-ethynyl-closo-1,7-dodecaborane

: 54-42-2
5-Iodo-2'-deoxyuridine

: 5-[(1,7-dicarba-closo-dodecaboran-9-yl)ethyn-1-yl]-2′-deoxyuridine

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 80℃; Sonogashira Cross-Coupling; Inert atmosphere;	100%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 18162-48-6
tert-butyldimethylsilyl chloride

: 148134-86-5
2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine

Conditions

Conditions	Yield
With 1H-imidazole In pyridine for 33h;	99%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h;	99.8%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 60h;	99%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 54-42-2
5-Iodo-2'-deoxyuridine

: 104375-88-4
2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-iodouridine

Conditions

Conditions	Yield
With pyridine Ambient temperature;	99%
With pyridine; triethylamine at 20℃; for 1h;	98%
With pyridine In triethylamine at 20℃; for 5h;	96%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 108-24-7
acetic anhydride

: 1956-30-5
3',5'-O-diacetyl-5-iodo-2'-deoxyuridine

Conditions

Conditions	Yield
With pyridine at 20℃; for 16.5h;	99%
With pyridine at 20℃;	98%
With pyridine at 25℃; for 20h;	97%

: 14115-48-1
3,3-bis-(trifluoromethyl)-4,4,4-trifluoro-1-butyne

: 54-42-2
5-Iodo-2'-deoxyuridine

: 1032735-58-2
5-(4,4,4-trifluoro-3,3-bis(trifluoromethyl)but-1-ynyl)-2'-deoxyuridine

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 22℃; for 96h; Sonogashira coupling; Inert atmosphere;	98%

: 141-32-2
acrylic acid n-butyl ester

: 54-42-2
5-Iodo-2'-deoxyuridine

: (E)-5-[2-(n-butyloxycarbonyl)vinyl]-2′-deoxyuridine

Conditions

Conditions	Yield
With 3,3′,3″-phosphinetriyltribenzenesulfonate; palladium diacetate; triethylamine In water; acetonitrile at 80℃; for 1.5h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere;	98%
With tri(3-sulfonatophenyl)phosphine trisodium salt; palladium diacetate; triethylamine In water; acetonitrile at 80℃; Heck reaction; Inert atmosphere;	74%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 54-42-2
5-Iodo-2'-deoxyuridine

: 5-methoxycarbonyl-2’-deoxyuridine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 70℃;	98%

...Expand

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

: 54-42-2
5-Iodo-2'-deoxyuridine

: 129507-76-2
5-iodo-3',5'-O-[(tetraisopropyl)disiloxane-1,3-diyl]-2'-deoxyuridine

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 12h;	97%
With pyridine at 20℃;	97%
With pyridine at 20℃;	84%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h; silylation;

: 54-42-2
5-Iodo-2'-deoxyuridine

: 98-80-6
phenylboronic acid

: 76756-28-0
1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-phenylpyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With palladium diacetate; sodium carbonate; triphenylphosphine In water; acetonitrile at 70 - 80℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere;	97%
With palladium diacetate; sodium carbonate; triphenylphosphine In water; acetonitrile at 70 - 80℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere;	97%
With C30H24Cl2N2O10Pd2S2(2-)*2Na(1+); triethylamine In water at 60℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	93%

: 1945-84-2
2-ethynylpyridine

: 54-42-2
5-Iodo-2'-deoxyuridine

: 78824-48-3
5-(2-pyridylethynyl)-2'-deoxyuridine

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	97%

: 592-76-7
1-Heptene

: 54-42-2
5-Iodo-2'-deoxyuridine

: 96962-44-6
5-(hept-1-en-1-yl)-2'-deoxyuridine

Conditions

Conditions	Yield
With tributyl-amine; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 0.333333h; Heck reaction; Microwave irradiation;	97%
With tributyl-amine; palladium diacetate In 1,4-dioxane; N,N-dimethyl-formamide at 100℃; for 0.333333h; Microwave irradiation;	97%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 2-(tri-n-butylstannyl)benzofuran

: 1449768-52-8
5-(benzofuran-2-yl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 90℃; Stille Cross Coupling;	97%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 211510-45-1
but-1-yn-4-yl thiobenzoate

: 647852-33-3
5-(4-benzoylthio-1-butynyl)-2'-deoxyuridine

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 22 - 24℃;	96%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 75-36-5
acetyl chloride

: 1956-30-5
3',5'-O-diacetyl-5-iodo-2'-deoxyuridine

Conditions

Conditions	Yield
With acetic anhydride; acetic acid 1.) 0 deg C, 1 h, 2.) RT, 24 h;	95%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 77-78-1
dimethyl sulfate

: 35695-25-1
5-iodo-3-methyl-2′-deoxyuridine

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.166667h;	95%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 422284-33-1
3-methyl-N-(prop-2-yn-1-yl)butanamide

: 5-[3-(3-methylbutyrylamino)prop-1-ynyl]-2'-deoxyuridine

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 20℃; for 4h;	95%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 829-85-6
diphenylphosphane

: 939057-19-9
5-diphenylphosphine-2'-deoxyuridine

Conditions

Conditions	Yield
With triethylamine; palladium diacetate In N,N-dimethyl-formamide at 60℃; for 0.5h;	95%

: 10365-98-7
3-methoxyphenylboronic acid

: 54-42-2
5-Iodo-2'-deoxyuridine

: 92510-79-7
5-(3-methoxyphenyl)-2'-deoxyuridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In water; N,N-dimethyl-formamide at 60℃; Suzuki cross-coupling; Inert atmosphere;	95%
With [Pd(phthalimidate)2(1,3,5-triaza-7-phosphaadamantane)2]; triethylamine In water at 20 - 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;

: 772-38-3
4-tert-Butylphenylacetylene

: 54-42-2
5-Iodo-2'-deoxyuridine

: 596107-17-4
5-((4-tert-butylphenyl)ethynyl)-2'-deoxyuridine

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 40℃; for 25h; Sonogashira coupling;	94%
With copper(l) iodide; tetra-(n-butyl)ammonium iodide; triphenylphosphine; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Sonogashira coupling;	76%
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide

: 54-42-2
5-Iodo-2'-deoxyuridine

: 118486-94-5
2-(tributylstannyl)furan

: 92233-50-6
5-furan-2-yl-1-(β-D-2-deoxyribofuranos-1-yl)uracil

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 90℃; for 2h; Stille coupling;	94%
bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 90℃; for 2h; Stille coupling;	94%
With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane	94%
With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 90℃; Stille Cross Coupling;

: 54-42-2
5-Iodo-2'-deoxyuridine

: 78-27-3
1-Ethynyl-1-cyclohexanol

: 936332-87-5
5-((1-hydroxycyclohexyl)ethynyl)-2'-deoxyuridine

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 50℃; for 7h; Sonogashira coupling;	94%
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide

: 16419-60-6
2-Methylphenylboronic acid

: 54-42-2
5-Iodo-2'-deoxyuridine

: 1373213-45-6
5-(2-methylphenyl)-2'-deoxyuridine

Conditions

Conditions	Yield
With sodium tetrachloropalladate; trisodium tris(3-sulfophenyl)phosphine; potassium hydroxide In water at 100℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;	94%
With sodium tetrachloropalladate(II); potassium hydroxide In water at 100℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Microwave irradiation;	30%
With sodium tetrachloropalladate(II); potassium hydroxide In water at 100℃; for 24h; Concentration; Time; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry;	22%

: 98437-24-2
benzofuran-2-boronic acid

: 54-42-2
5-Iodo-2'-deoxyuridine

: 1449768-52-8
5-(benzofuran-2-yl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With [Pd(succinimidate)2(1,3,5-triaza-7-phosphaadamantane)2]; triethylamine In water at 80℃; for 0.0833333h; Catalytic behavior; Concentration; Suzuki-Miyaura Coupling; Microwave irradiation; Inert atmosphere;	94%
With C30H24Cl2N2O10Pd2S2(2-)*2Na(1+); triethylamine In water at 60℃; for 3h; Solvent; Reagent/catalyst; Temperature; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	89%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 123-62-6
propionic acid anhydride

: 4833-05-0
3′,5′-bis-O-propionyl-5-iodo-2′-deoxyuridine

Conditions

Conditions	Yield
With pyridine at 60℃; for 8h; Inert atmosphere;	93%
With pyridine	85%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 7486-35-3
tri-n-butyl(vinyl)tin

: 55520-67-7
5-vinyl-2'-deoxyuridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 12h; Inert atmosphere; Reflux;	92%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Inert atmosphere; Reflux;	50%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Heating;	47%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 1066-54-2
trimethylsilylacetylene

: 151362-01-5
1-(2-deoxy-β-D-ribofuranosyl)-5-[2-(trimethylsilyl)ethynyl]uracil

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 55℃; for 24h; Sonogashira coupling;	92%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 50℃; for 3.5h; Schlenk technique; Inert atmosphere;	85%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile for 3.5h; Inert atmosphere; Heating;	82%

: 1765-93-1
4-fluoroboronic acid

: 54-42-2
5-Iodo-2'-deoxyuridine

: 5-(4'-fluorophenyl)-2'-deoxyuridine

Conditions

Conditions	Yield
With palladium diacetate; sodium carbonate; tris-(m-sulfonatophenyl)phosphine In water; acetonitrile at 80℃; Suzuki coupling;	92%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In water; N,N-dimethyl-formamide at 60℃; Suzuki cross-coupling; Inert atmosphere;	78%
With palladium diacetate; sodium carbonate; triphenylphosphine In water at 120℃; for 0.166667h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; Microwave irradiation;	74%
With [Pd(phthalimidate)2(1,3,5-triaza-7-phosphaadamantane)2]; triethylamine In water at 20 - 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;

: 10602-06-9
methyl 3-ethynylbenzoate

: 54-42-2
5-Iodo-2'-deoxyuridine

: 3-[3-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-2,3-dihydro-furo[2,3-d]pyrimidin-6-yl]-benzoic acid methyl ester

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 55℃; for 12h;	92%

(+)-5-Iodo-2'-deoxyuridine Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

(+)-5-Iodo-2'-deoxyuridine Specification

The Uridine,2'-deoxy-5-iodo-, with the CAS registry number 54-42-2 and EINECS registry number 200-207-8, has the IUPAC name of 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione. It is a kind of crystalline solid which is sensitive to air and light, and it is always used as antiviral. The molecular formula of the chemical is C₉H₁₁IN₂O₅.

The physical properties of Uridine,2'-deoxy-5-iodo- are as followings: (1)ACD/LogP: -0.59; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1; (4)ACD/LogD (pH 7.4): -1; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12; (8)ACD/KOC (pH 7.4): 6; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 99.1 Å²; (13)Index of Refraction: 1.715; (14)Molar Refractivity: 64.752 cm³; (15)Molar Volume: 164.874 cm³; (16)Polarizability: 25.67×10^-24cm³; (17)Surface Tension: 87.47 dyne/cm; (18)Density: 2.148 g/cm³.

Preparation: You can start with propiolic alcohol by oxidation and esterification, then it reacts with 2-amino-oxazoline nucleoside. By a series of acylation, bromination, catalytic hydrogenation and hydrolysis, you can get the product.

You should be cautious while dealing with this chemical. It may cause cancer and heritable genetic damage. Therefore, you had better take the following instructions: Do not breathe dust; Avoid exposure - obtain special instruction before use; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible); Wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: I\C1=C\N(C(=O)NC1=O)C2C[C@H](O)[C@@H](CO)O2
(2)InChI: InChI=1/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7?/m0/s1
(3)InChIKey: XQFRJNBWHJMXHO-GFCOJPQKBD

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	1gm/kg (1000mg/kg)	JNCI, Journal of the National Cancer Institute. Vol. 62, Pg. 911, 1979.
mouse	LD50	oral	> 10gm/kg (10000mg/kg)	Drugs in Japan Vol. -, Pg. 153, 1995.
rat	LD50	intraperitoneal	4gm/kg (4000mg/kg)	Advances in Teratology. Vol. 3, Pg. 181, 1968.

Product Name

(+)-5-Iodo-2'-deoxyuridine

Synthetic route

(+)-5-Iodo-2'-deoxyuridine Consensus Reports

(+)-5-Iodo-2'-deoxyuridine Specification

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