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Propargyl bromide is used as an alkylating agent as well as an intermediate for the synthesis of organic compounds, agrochemicals and pharmaceuticals. It reacts with magnesium in presence of ether to get a Grignard reagent namely allenylmagnesium bromide, which on further reaction with propargyl bromide prepares bis-allene 1,2,4,5-hexatetraene. Also, used as metal brightening agents, corrosion inhibitor and soil fumigant.
With Mg in ether, generates allenylmagnesium bromide which can be coupled with a further molecule of propargyl bromide to give the bis-allene 1,2,4,5-hexatetraene: Org. Synth. Coll., 7, 485 (1990). Diels-Alder reaction of the product with Dimethyl acetylenedicarboxylate, A11437 leads to a para-cyclophane.
Barbier-type reaction with aldehydes in aqueous THF gives the secondary alcohols in moderate to good yields: Synth. Commun., 25, 2923 (1995); partial rearrangement to the allene could occur; cf Allyl bromide, A11766, for similar reactions. For reaction with aldehydes in the presence of Zn in THF, and transformation of the resulting secondary alcohols into pyruvate esters, see: J. Chem. Chem. Commun ., 1289 (1991).
For conversion to dimethyl-2-propynylsulfonium bromide and condensation with 2,4-pentanedione and other active methylene compounds in a versatile, high-yield synthesis of substituted furans, see: J. Chem. Soc., Perkin 1, 65 (1973); Org. Synth. Coll ., 6, 31 (1988).
For diastereoselective propargylation of ɑ -alkoxy aldehydes and application in the synthesis of oxygenated acyclic natural products, see: J. Org. Chem., 60, 3257 (1995).
Zhou, C.; Gao, Y.; Chen, D. Investigation of pyridine/propargyl bromide reaction and strong fluorescence enhancements of the resultant poly (propargyl pyridinium bromide). J. Phys. Chem. B 2012, 116 (37), 11552-11559.
Musalova, M. V.; Musalov, M. V.; Potapov, V. A.; Amosova, S. V. Selective synthesis of allenyl aryl tellurides from diaryl ditellurides and propargyl bromide. Russ. J. Org. Chem. 2012, 48 (12), 1569-1570.
Mentions de danger (UE): H225-H301-H333-H314-H318-H361-H335-H336-H373-H304
Highly flammable liquid and vapour. Toxic if swallowed. May be harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of damaging fertility or the unborn child. May cause respiratory irritation. May cause drowsiness or dizziness. May cause damage to organs through prolonged or repeated exposure. May be fatal if swallowed and enters airways.
Mentions de prudence: P210-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.