2-(2-Bromoethyl)-1,3-dioxolane

• Catalog No.: A11441
• CAS Number: 18742-02-4
• M. F.: C5H9BrO2
• M. W.: 181.02776
• Purity: 95%, stab. with silver

SYNONYMS

• Title: 2-(2-溴乙基)-1,3-二氧戊环烷
• IUPAC name: 2-(2-bromoethyl)-1,3-dioxolane
• IUPAC Traditional name: 2-(2-bromoethyl)-1,3-dioxolane
• Synonyms: 3-Bromopropionaldehyde ethylene acetal; 3-Bromopropanal 1,2-ethanediol acetal

DATABASE IDS

• Beilstein Number: 103516
• CAS Number: 18742-02-4
• MDL Number: MFCD00003216
• EC Number: 242-551-1

PROPERTIES

• Purity: 95%, stab. with silver
• Boiling Point: 68-70°C/8mm
• Density: 1.512
• Flash Point: 65°C(149°F)
• Refractive Index: 1.4790
• GHS Hazard statements: H315-H319-H335-H227
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Light Sensitive
• TSCA Listed: 否

REFERENCES

• For a review of 3-carbon homologating reagents, including many examples of Grignard and organocuprate reactions of these molecules, see: Chem. Rev., 84, 409 (1984).
• Masked ?-formylethyl synthon, compare preceding entry. The derived Grignard, which, unlike the dioxane analogue, is unstable above room temperature, shows similar attenuated reactivity in comparison with simple alkyl Grignard reagents, reacting with acid chlorides to give -ketoaldehydes without carbinol formation, and with enones to give, at low temperatures, predominantly the 1,4-addition product without the need for Cu catalysis:Tetrahedron Lett., 28, 3217 (1987).
• The Grignard undergoes coupling reactions (CuBr₂ + LiCl catalysis) with allylic halides: Tetrahedron Lett., 4549 (1979); J. Org. Chem., 46, 1504 (1981), allylic acetates: J. Am. Chem. Soc., 104, 2269 (1982), and primary alkyl bromides: J. Org. Chem., 48, 1767 (1983).