| Identification | Back Directory | [Name]
2,2,3-tribromopropanal | [CAS]
26944-17-2 | [Synonyms]
Propanal, 2,2,3-tribromo-
2,2,3-Tribromopropionaldehyde | [Molecular Formula]
C3H3Br3O | [MDL Number]
MFCD16620398 | [MOL File]
26944-17-2.mol | [Molecular Weight]
294.77 |
| Hazard Information | Back Directory | [Uses]
2,2,3-Tribromopropanal is a versatile reagent that was used for the first time in the 1950s. It is used as a reagent in the Skraup-type synthesis of 3-bromoquinolin-6-ols. 2,2,3-Tribromopropanal is also used in the preparation of quinolinyloxyacetamides, a novel class of tubulin polymerization inhibitors with fungicidal activity. | [Synthesis]
Example 4 Preparation of 2,2,3-tribromopropionaldehyde: Bromine (1.79 mol) was slowly added dropwise to a solution of acrolein (100.0 g, 1.78 mol) dissolved in dichloromethane (150 ml) over a period of 3 hours. The reaction temperature needs to be controlled to be maintained between 40°C and 50°C during the dropwise addition. Subsequently, the reaction mixture was heated to 70 °C and bromine (285.8 g, 1.78 mol) was added slowly dropwise over a period of 4 hours. It was necessary to ensure that the temperature of the solution was maintained between 70 °C and 80 °C during the dropwise addition. Upon completion of the reaction, the mixture was cooled to room temperature and the volatile components were removed by evaporation to afford 2,2,3-tribromopropanal in 99.4% yield. | [References]
[1] Patent: US4489098, 1984, A
[2] Patent: US4489098, 1984, A
[3] Patent: US4489098, 1984, A
[4] Synlett, 2014, vol. 25, # 6, p. 858 - 862
[5] ChemMedChem, 2018, vol. 13, # 12, p. 1160 - 1164 |
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