{{short description|Chemical compound}} {{Chembox |Name = Propargyl bromide |ImageFile = Propargyl bromide.svg |PIN = 3-Bromoprop-1-yne |OtherNames = 3-Bromo-1-propyne<br />Bromopropyne<br />1-Brom-2-propin<br />1-Bromo-2-propyne<br />''gamma''-Bromoallylene<br />2-Propynyl bromide<br />Propargyl bromide<br />Propynyl bromide |Section1={{Chembox Identifiers |CASNo = 106-96-7 |UNII_Ref = {{fdacite|correct|FDA}} |UNII = F3H7ZXK9ZU |ChemSpiderID = 7554 |InChI = InChI=1S/C3H3Br/c1-2-3-4/h1H,3H2 |PubChem = 7842 |SMILES = BrCC#C }} |Section2={{Chembox Properties |Appearance = colourless liquid |BoilingPtC = 89 |BoilingPt_ref = <ref name=GESTIS>{{GESTIS|ZVG=490139}}</ref> |Density = 1.57 g/mL (20 °C)<ref name=GESTIS/> |C=3 | H=3 | Br=1 |LogP = 1.179 |MeltingPtC = -61.1 |MeltingPt_ref = <ref name=GESTIS/> |Solubility = insoluble |SolubleOther = Soluble in organic solvents |VaporPressure = 72 mbar (20 °C)<ref name=GESTIS/>}} |Section3={{Chembox Structure }} |Section7={{Chembox Hazards |AutoignitionPtC = 324 |AutoignitionPt_ref = <ref name=GESTIS/> |FlashPtC = 18 |FlashPt_ref = <ref name=GESTIS/> |MainHazards = Highly Flammable, Toxic, Corrosive |NFPA-H = 3 |NFPA-F = 3 |NFPA-R = 4 |NFPA-S = }} }}
'''Propargyl bromide''', also known as '''3-bromo-prop-1-yne''', is an organic compound with the chemical formula HC≡CCH<sub>2</sub>Br. A colorless liquid, it is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is used as a reagent in organic synthesis.
== Applications and production== Propargyl bromide may be produced by the treatment of propargyl alcohol with phosphorus tribromide.<ref name="FreePatentsOnline">{{cite web | url=http://www.freepatentsonline.com/6794551.html | title= Process for Producing Propargyl Bromide | accessdate= November 7, 2012}}</ref>
== Reactions == Propargyl bromide is an alkylating agent. For example, it reacts with dimethylsulfide, it reacts to give the sulfonium salt:<ref>{{cite journal |doi=10.15227/orgsyn.053.0001|author=P. D. Howes, C. J. M. Stirling|title=3-Acetyl-2,4-Dimethylfuran |journal=Organic Syntheses |year=1973 |volume=53 |page=1 }}</ref> :{{chem2|HCCCH2Br + S(CH3)2 -> [HCCCH2S(CH3)2]Br}} It alkylates even weakly basic amines such as aniline.<ref>{{cite journal |doi=10.15227/orgsyn.089.0294|title=Synthesis of Quinolines by Electrophilic Cyclization of N-(2-Alkynyl)Anilines: 3-Iodo-4-Phenylquinoline |journal=Organic Syntheses |year=2012 |volume=89 |page=294|author=Yu Chen, Anton Dubrovskiy, Richard C. Larock |doi-access=free }}</ref>
Aldehydes react with propargyl bromide in a Barbier-type reaction to yield alkynyl alcohols:<ref>{{cite journal |last1=Jõgi |first1=Artur |last2=Mäeorg |first2=Uno |title=Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. {{chem|N|H|4|Cl}} Solution |journal=Molecules |date=30 November 2001 |volume=6 |issue=12 |pages=964–968 |doi=10.3390/61200964 |doi-access=free |pmc=6236518 }}</ref>
:Barbier reaction
At low temperatures, upon treatment with magnesium, propargyl bromide gives the Grignard reagent formally derived from allenyl bromide, i.e., CH<sub>2</sub>=C=CHMgBr.<ref>{{OrgSynth|author=Henning Hopf, Ingrid Böhm, and Jürgen Kleinschroth|year=1990|title=Diels-Alder Reaction of 1,2,4,5-Hexatetraene: Tetramethyl[2.2]paracyclophane-4,5,12,13-tetracarboxylate|volume=60|pages=41|doi=10.15227/orgsyn.060.0041}}</ref>
Propargyl bromide and its ether derivatives participate in azide-based click reactions.<ref>{{cite journal |doi=10.1002/anie.200454078 |title=Efficiency and Fidelity in a Click-Chemistry Route to Triazole Dendrimers by the Copper(I)-Catalyzed Ligation of Azides and Alkynes |date=2004 |last1=Wu |first1=Peng |last2=Feldman |first2=Alina K. |last3=Nugent |first3=Anne K. |last4=Hawker |first4=Craig J. |last5=Scheel |first5=Arnulf |last6=Voit |first6=Brigitte |last7=Pyun |first7=Jeffrey |last8=Fréchet |first8=Jean M. J. |last9=Sharpless |first9=K. Barry |last10=Fokin |first10=Valery V. |journal=Angewandte Chemie International Edition |volume=43 |issue=30 |pages=3928–3932 |pmid=15274216 }}</ref>
==Safety== Propargyl bromide is a lachrymator and an alkylating agent,<ref name="toxnet">{{cite web | url=https://www.nlm.nih.gov/toxnet/index.html | title= 3-Bromo-1-Propyne | access-date= November 3, 2012}}</ref> This liquid acetylenic endothermic compound may be decomposed by mild shock, and when heated under confinement, it decomposes with explosive violence and may detonate. Addition of 20—30 wt% of toluene makes propargyl bromide insensitive in laboratory impact and confinement tests.<ref>{{cite book |doi=10.1016/B978-0-08-100971-0.00055-X |chapter=C1 |title=Bretherick's Handbook of Reactive Chemical Hazards |date=2017 |pages=81–882 |isbn=978-0-08-100971-0 |editor1-first=P.G. |editor1-last=Urben }}</ref> == See also == *Propargyl *Propargyl chloride *Propargyl alcohol *Allyl bromide
==References==
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Category:Organobromides Category:Propargyl compounds