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18742-02-4 - 2-(2-Bromoethyl)-1,3-dioxolane, 95%, stab. with silver - 3-Bromopropanal 1,2-ethanediol acetal - 3-Bromopropionaldehyde ethylene acetal - A11441 - Alfa Aesar

A11441 2-(2-Bromoethyl)-1,3-dioxolane, 95%, stab. with silver

CAS-Nummer
18742-02-4
Synonyme
3-Bromopropanal 1,2-ethanediol acetal
3-Bromopropionaldehyde ethylene acetal

Größe Preis ($) Menge Verfügbarkeit
10g 37,44
50g 125,19
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2-(2-Bromoethyl)-1,3-dioxolane, 95%, stab. with silver

MDL
MFCD00003216
EINECS
242-551-1

Chemische Eigenschaften

Formel
C5H9BrO2
Molmasse
181.04
Siedepunkt
68-70°/8mm
Flammpunkt
65°(149°F)
Dichte
1.512
Brechungsindex
1.4790
Sensitivität
Light Sensitive
Löslichkeit
It is immiscible with water.

Anwendungen

2-(2-Bromoethyl)-1,3-dioxolane is used as a pharmaceutical intermediate, dioxolanes, acetals, ketals, building blocks, chemical synthesis, organic building blocks and oxygen compounds. 1,1-(Ethylenedioxy)-3-bromopropane is used in the synthesis of EGFR inhibitors. Also used in the synthesis of orally active agents of cancer and cell proliferation with quinoline substructures. It is also used as flavouring agent.

Bemerkungen

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8°C. Light sensitive. Store under inert gas.

Literaturverweise

George Buechi.; Hans Wuest. Synthesis of (+-)-nuciferal. J. Org. Chem.196934, (4), 1122-1123.

Ehud Keinan.; Zeev Roth. Regioselectivity in organo-transition-metal chemistry. A new indicator substrate for classification of nucleophiles. J. Org. Chem.198348, (10), 1769-1772.

Masked ß-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).

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).

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H301-H315-H319-H335-H227

Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Combustible liquid.

Sicherheitshinweise: P210-P261-P280-P301+P310-P305+P351+P338-P304+P340-P362-P312-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
103516
Gefahrenklasse
6.1
Verpackungsgruppe
III
Harmonized Tariff Code
2932.99
TSCA
No

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