137500-15-3

Basic information

• Product Name: 5-vinyl-2,4-dichloropyrimidine
• CAS NO: 137500-15-3
• Molecular Weight: 175.017
• Mol File: 137500-15-3.mol

Chemical Properties

• Boiling Point: 266.0±20.0 °C(Predicted)
• Density: 1.392±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 5-vinyl-2,4-dichloropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-vinyl-2,4-dichloropyrimidine(137500-15-3)
• EPA Substance Registry System: 5-vinyl-2,4-dichloropyrimidine(137500-15-3)

Safety Data

• Hazardous Substances Data: 137500-15-3(Hazardous Substances Data)

Upstream product

• 37107-81-6 5-vinyluracil 
• 36082-50-5 2,4-dichloro-5-bromopyrimidine 
• 7486-35-3 tri-n-butyl(vinyl)tin 

Downstream Products

• 1305318-34-6 2,4-dichloro-5-(1-phenylethyl)pyrimidine 

Relevant articles and documents

Synthesis and cytotoxic activity of 5-(1-hydroxy-2-haloethyl)-, 5-oxiranyl- and (E)-5-(2-iodovinyl)-2,4-dichloro (or dimethoxy) pyrimidines

A series of 5-(1-hydroxy-2-haloethyl) 6, 7, 13, 14a, 5-oxiranyl 8, 9 and (E)-5-(2-iodovinyl)-2,4-dichloro(or dimethoxy)pyrimidines 11, 12 were synthesized for evaluation as cytotoxic agents. The nuclear C-2 and C-4 substituents were determinants of activity since the 2,4-dichloro compounds 6, 8 and 11 were more potent (ED50 = 0.2-0.3 μg/ml) than the corresponding 2,4-dimethoxypyrimidine analogues 7, 9 and 12 (ED50 = 4-28 μg/ml), relative to melphalan (ED50 = 0.15 μg/ml), in the in vitro L1210 screen. Within the 2,4-dichloro series of compounds 6, 8, 11, the C-5 substitutent was not a determinant of activity. In contrast, in the 2,4-dimethoxypyrimidine series, the C-5 substituents influenced activity significantly where the relative potency order was oxiranyl 9 > -CH(OH)CH2I 7 > (E)-CH = CHI 12 > CH(OH)CHI2 13, CH(OH)CHBr(I) 14a and CH(Br)CHOH(I) 14b. The most active compound (E)-5-(2-iodovinyl)-2,4-dichloropyrimidine 11 exhibited weak activity in the in vivo P388 screen (% T/C = 116 for a 10 mg/kg ip dose) relative to the reference drug 5-fluorouracil (% T/C = 135 for a 20 mg/kg dose).

Superacid-promoted additions involving vinyl-substituted pyrimidines, quinoxalines, and quinazolines: Mechanisms correlated to charge distributions

The superacid-promoted reactions of vinyl-substituted N-heterocycles have been studied. Diprotonated pyrimidines, quinoxalines, and quinazolines exhibit an unusual regioelectronic effect that controls the type of addition reaction observed. Depending on the ring position of the vinyl substituent, either conjugate addition or Markovnikov addition occurs. The mode of addition has been shown to correlate well to NBO calculated charges.