69304-49-0

Basic information

• Product Name: (E)-5-(2-BROMOVINYL)URACIL
• Synonyms: (e)-5-(2-bromoethenyl)-2,4(1h,3h)-pyrimidinedione;5-(2-bromoethenyl)-4(1(e)-3h)-pyrimidinedione;5-(2-bromovinyl)uracil;bromovinyluracil;bvuracil;(E)-5-(2-BROMOVINYL)URACIL;5-(TRANS-2-BROMOVINYL)URACIL;5-[(E)-2-Bromoethenyl]uracil
• CAS NO: 69304-49-0
• Molecular Formula: C₆H₅BrN₂O₂
• Molecular Weight: 217.02
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Building Blocks;C6 to C8;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 69304-49-0.mol

Chemical Properties

• Melting Point: 189-194 °C (dec.)(lit.)
• Appearance: /
• Density: 1.881
• Refractive Index: 1.685
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 7.54±0.10(Predicted)
• CAS DataBase Reference: (E)-5-(2-BROMOVINYL)URACIL(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-5-(2-BROMOVINYL)URACIL(69304-49-0)
• EPA Substance Registry System: (E)-5-(2-BROMOVINYL)URACIL(69304-49-0)

Safety Data

• WGK Germany: 2
• RTECS: UV9020500
• Hazardous Substances Data: 69304-49-0(Hazardous Substances Data)

Usage

Chemical Properties

Beige Solid

InChI:InChI=1/C6H5BrN2O2/c7-2-1-4-3-8-6(11)9-5(4)10/h1-3H,(H2,8,9,10,11)/b2-1+

Upstream product

• 57412-59-6 (E)-5-(2-carboxyvinyl)uracil 
• 1195-08-0 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde 
• 134700-28-0 E-5-(2-bromovinyl)-2,4-dimethoxypyrimidine 
• 37107-81-6 5-vinyluracil 

Downstream Products

• 62785-91-5 furo[2,3-d]pyrimidin-2(3H)-one 
• 185816-33-5 3-benzoyl-5-(2-bromovinyl)uracil 
• 134700-19-9 (E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine 
• 134700-20-2 α-(E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine 
• 258334-04-2 5-((E)-2-Bromo-vinyl)-1-((1S,7R)-4,4-diphenyl-3,5-dioxa-bicyclo[5.1.0]oct-1-ylmethyl)-1H-pyrimidine-2,4-dione 
• 161105-93-7 L-BVOddU 
• 161105-93-7 D-BVOddU 
• 294867-93-9 1-((2R,3S,4S,5R)-4-Benzyloxy-3-fluoro-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-5-((E)-2-bromo-vinyl)-4-hydroxy-1H-pyrimidin-2-one 
• 294867-95-1 1-((2S,3S,4S,5R)-4-Benzyloxy-3-fluoro-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-5-((E)-2-bromo-vinyl)-4-hydroxy-1H-pyrimidin-2-one 
• 134699-93-7 (E)-5-(2-bromovinyl)-2'-deoxy-4'-thiouridine 
• 191794-49-7 1-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-((E)-2-bromo-vinyl)-1H-pyrimidine-2,4-dione 
• 87782-40-9 Benzoic acid (2R,3R,4S,5R)-5-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-4-fluoro-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 
• 87782-46-5 5(E)-(2-bromovinyl)-1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil 
• 91897-93-7 (E)-5-(2-bromovinyl)-1-((2-hydroxyethoxy)methyl)pyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

Syntheses of 5-(2-radiohaloethyl)- and 5-(2-radiohalovinyl)-2′-deoxyuridines. Novel types of radiotracer for monitoring cancer gene therapy with PET

Syntheses of 5-(2-[18F]fluoroethyl)- (1) 5-(2-[80Br] bromoethyl), (2), undeprotected (E)-5-(2-[18F]fluorovinyl)- (3) and (E)-5-(2-[80Br]bromovinyl),2′-deoxyuridines (4) as the tracers for monitoring cancer gene therapy with positron emission tomography were described. Decay corrected radiochemical yield and synthesis time including labeling and HPLC purification from end of bombardment for 1 was 9.5% and 2 hours, respectively; yield and time for 2 was 16% and 2 hours, respectively. Chemical (approximate to radiochemical) yield and time for synthesis of 3 was 7.5% and 7 minutes, respectively. Radiochemical yield and synthesis time including labeling and HPLC purification of an analytical sample of 4 was 60% and 30 minutes, respectively. Both 2 and 4 received the side reactions during HPLC purification, i.e. ring closure and cleavage of glycosidic bond, respectively. Application of 2 and 4 needed to be confirmed by in vitro or in vivo experiments. Radiochemical yield of 1 could be optimized by employing a modified protocol for preparation of its precursor. The preparation of fluorovinyl counterparts had demonstrated the potential utility of the stannane, 3-tolyl-3′,5′-di-O-acetyl-(E)-5-(2-stannylvinyl)- 2′-deoxyuridine 7. Copyright

Steric fixation of bromovinyluracil: Synthesis of furo[2,3-d]pyrimidine nucleosides

A new synthetic proccdure for the preparation of 5,6-dihydrofuro[2,3-d]pyrimidin-2(3H)-one (3) and its deoxyriboside 8 is reported. Compound 3 undergoes nucleophilic reactions with various agents to yield 5-substituted uracil derivatives. The dehydro derivative of 3, furo[2,3-d]pyrimidin-2(3H)-one (18) was synthesized by cyclization of BVU 15, which made us develop a reproducible and high yield method for the synthesis of BV(D)U. Starting from 18, the α-deoxyriboside 20 and the β-riboside 22 were prepared.

Antiviral pyrimidine nucleosides

Pyrimidine 4'-thionucleosides of the formula I STR1 wherein Y is hydroxy or amino, and X is chloro, bromo, iodo, trifluoromethyl, C2-6 alkyl, C2-6 alkenyl, C2-6 haloalkenyl or C2-6 alkynyl and physiologically functional derivatives thereof. These compounds have utility as anti-vital agents.

Preparation of thionucleosides

The invention relates to the preparation of homochiral thiolactones which have application in the synthesis of 3?- and 4?- thionucleosides. Substituents on the thiolactone can be used to influence the configuration of the C-1? position in the final nucleoside. Configuration at the C-4? position is controlled by use of the appropriate homochiral glycidol as starting material in the synthesis of the thiolactone. This process also offers the possibility of introducing substituents diastereoselectively in the C-2? and C-3? positions.

2'Deoxy-5-(2-halogenovinyl)-uridines, pharmaceutical compositions and method of use

The novel substance E-5-(2-bromovinyl)-2'-deoxyuridine and its corresponding iodovinyl derivative are gifted with specific antiviral activities towards herpes simplex virus. They may be synthesized by a condensation reaction followed by separation of anomers.

Synthesis of Some 5-Halogenovinyl Derivatives of Uracil and their Conversion into 2'-Deoxyribonucleosides

Treatment of 5-formyluracil with malonic acid in the presence of piperidine gave (E)-5-(2-carboxyvinyl)uracil which, upon reaction with the appropriate N-halogenosuccinimide, gave (E)-5-(2-bromovinyl)uracil, (E)-5-(2-chlorovinyl)uracil, and (E)-5-(2-iodovinyl)uracil.The last mentioned compound was also obtained by the action of iodine chloride on 5-vinyluracil. 5-(1-Chlorovinyl)uracil upon treatment with bromine gave 5-(2-bromo-1-chlorovinyl)uracil which reacted with sodium methoxide to give 5-bromoethynyluracyl. (E)-5-(2-Bromovinyl)uracil was converted into its trimethylsilyl derivative which was condensed with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride to give the α- and β-anomers of the blocked deoxyribonucleoside.Removal of the p-toluoyl blocking groups with sodium methoxide afforded (E)-5-(2-bromovinyl)-1-(2-deoxy-α-D-erythro-pentofuranosyl)uracil and (E)-5-(2-bromovinyl)-2'-deoxyuridine.A similar series of reactions gave (E)-5-(2-iodovinyl)-2'-deoxyuridine and 5-(2-bromo-1-chlorovinyl)-2'-deoxyuridine. 5-(1-Chlorovinyl)uracil could be condensed similarly with the blocked sugar derivative to give the α- and β-anomers of the blocked deoxyribonucleoside.Attempted removal of the groups with sodium methoxide gave 2'-deoxy-5-ethynyluridine and mild treatment with methanolic ammonia gave the same product and some 2'-deoxy-5-ethynyl-5'-O-(p-toluoyl)uridine. 5-(1-Chlorovinyl)-2'-deoxyuridine was obtained by the addition of HCl to 2'-deoxy-5-ethynyluridine.Aspects of the elimination reactions of 5-(halogenovinyl)uracil derivatives are discussed.