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
• Article Data: 6

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

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

Downstream Products

• 66-22-8 uracil 
• 69304-47-8 (E)-5-(2-bromovinyl)-2'-deoxyuridine 
• 1202696-97-6 1-benzyl-5-((E)-2-bromovinyl)pyrimidine-2,4(1H,3H)dione 
• 1006598-32-8 1-(3',5'-di-O-benzoyl-2',2'-difluoro-α-D-pentofuranos-1'-yl)-5-(E)-bromovinyluracil 
• 1006598-31-7 1-(3',5'-di-O-benzoyl-2',2'-difluoro-β-D-pentofuranos-1'-yl)-5-(E)-bromovinyluracil 
• 164013-29-0 1-[(1'S,2'R)-1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl-5-[(E)-2-bromoethenyl]-2,4(1H,3H)-pyrimidinedione 
• 73446-75-0 (E)-5-(2-bromovinyl)-1-<2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>uracil 
• 73446-74-9 (E)-5-(2-bromovinyl)-2'-deoxy-3',5'-di-O-(p-toluoyl)uridine 
• 91897-93-7 (E)-5-(2-bromovinyl)-1-((2-hydroxyethoxy)methyl)pyrimidine-2,4(1H,3H)-dione 
• 87782-46-5 5(E)-(2-bromovinyl)-1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil 
• 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 
• 134699-93-7 (E)-5-(2-bromovinyl)-2'-deoxy-4'-thiouridine 
• 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 
• 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 

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

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.

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.