Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals,[2] synthetic perfumes[3] and other organic compounds. Physically, allyl bromide is a colorless liquid with an irritating and persistent smell, however, commercial samples are yellow or brown.[4] Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.[5]
^ abcdefghiCRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: others (link)
^ abYoffe, David; Frim, Ron; Ukeles, Shmuel D.; Dagani, Michael J.; Barda, Henry J.; Benya, Theodore J.; Sanders, David C. (2013-10-09), "Bromine Compounds", in Wiley-VCH Verlag GmbH & Co. KGaA (ed.), Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. 1–31, doi:10.1002/14356007.a04_405.pub2, ISBN978-3-527-30673-2, retrieved 2022-03-04
^PubChem. "Hazardous Substances Data Bank (HSDB) : 622". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-03-04.
^ abBolton, Roger (2001-04-15), "Allyl Bromide", in John Wiley & Sons, Ltd (ed.), Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, pp. ra045, doi:10.1002/047084289x.ra045, ISBN978-0-471-93623-7, retrieved 2022-03-04
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Allyl bromide 3 bromopropene is an organic halide It is an alkylating agent used in synthesis of polymers pharmaceuticals 2 synthetic perfumes 3 and other organic compounds Physically allyl bromide is a colorless liquid with an irritating and persistent smell however commercial samples are yellow or brown 4 Allyl bromide is more reactive but more expensive than allyl chloride and these considerations guide its use 5 Allyl bromide NamesPreferred IUPAC name 3 Bromoprop 1 eneOther names Allyl bromide3 Bromopropene3 Bromopropylene3 Bromo 1 propeneBromoallylene2 Propenyl bromideIdentifiersCAS Number 106 95 6 Y3D model JSmol Interactive imageInteractive imageChemSpider 7553 YECHA InfoCard 100 003 134EC Number 203 446 6PubChem CID 7841RTECS number UC7090000UNII FXQ8X2F74Z YUN number 1099CompTox Dashboard EPA DTXSID8024442InChI InChI 1S C3H5Br c1 2 3 4 h2H 1 3H2 YKey BHELZAPQIKSEDF UHFFFAOYSA N YInChI 1 C3H5Br c1 2 3 4 h2H 1 3H2Key BHELZAPQIKSEDF UHFFFAOYAISMILES BrCC CC CCBrPropertiesChemical formula C 3H 5BrMolar mass 120 977 g mol 1Appearance Clear to light yellow liquidOdor Unpleasant irritating pungentDensity 1 398 g cm3Melting point 119 C 182 F 154 K Boiling point 71 C 160 F 344 K Solubility in water 0 38 g 100 g H2O 1 log P 1 79 1 Vapor pressure 18 6 kPaMagnetic susceptibility x 58 6 10 6 cm3 mol 1 1 Refractive index nD 1 4697 20 C 589 2 nm Viscosity 0 471 cP 1 Dipole moment 1 9 D 1 ThermochemistryStd enthalpy offormation DfH 298 12 2 kJ mol 1 liquid 45 2 kJ mol 1 gas 1 Enthalpy of vaporization DfHvap 32 73 kJ mol 1 1 HazardsGHS labelling PictogramsSignal word DangerHazard statements H225 H301 H314 H330 H331 H340 H350 H400Precautionary statements P201 P202 P210 P233 P240 P241 P242 P243 P260 P261 P264 P270 P271 P273 P280 P281 P284 P301 P310 P301 P330 P331 P303 P361 P353 P304 P340 P305 P351 P338 P308 P313 P310 P311 P320 P321 P330 P363 P370 P378 P391 P403 P233 P403 P235 P405 P501NFPA 704 fire diamond 331Flash point 2 to 1 CAutoignitiontemperature 280 C 536 F 553 K Explosive limits 4 3 7 3 Threshold limit value TLV 0 1 ppm 1 TWA 0 2 ppm 1 STEL Safety data sheet SDS MSDS at Oxford UniversityRelated compoundsRelated compounds Allyl chlorideAllyl iodideExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Preparation 2 Reactions and uses 2 1 Electrophilic properties 2 2 Preparation of Grignard reagent 3 References 4 External linksPreparation EditAllyl bromide is produced commercially from allyl alcohol and hydrobromic acid 5 CH2 CHCH2OH HBr CH2 CHCH2Br H2OIt can also be prepared by the halogen exchange reaction between allyl chloride and hydrobromic acid or by the allylic bromination of propene 5 Reactions and uses EditElectrophilic properties Edit Allyl bromide is an electrophilic alkylating agent 4 It reacts with nucleophiles such as amines carbanions alkoxides etc to introduce the allyl group CH2 CHCH2Br Nu CH2 CHCH2Nu Br Nu is a nucleophile It is used in the synthesis of compounds containing the allyl functionality such as the pharmaceuticals methohexital secobarbital and thiamylal 2 Preparation of Grignard reagent Edit Allyl bromide reacts with magnesium metal in dry ether to form allylmagnesium bromide a Grignard reagent 6 CH2 CHCH2Br Mg CH2 CHCH2MgBrReferences Edit a b c d e f g h i CRC handbook of chemistry and physics a ready reference book of chemical and physical data William M Haynes David R Lide Thomas J Bruno 2016 2017 97th ed Boca Raton Florida 2016 ISBN 978 1 4987 5428 6 OCLC 930681942 a href Template Cite book html title Template Cite book cite book a CS1 maint others link a b Yoffe David Frim Ron Ukeles Shmuel D Dagani Michael J Barda Henry J Benya Theodore J Sanders David C 2013 10 09 Bromine Compounds in Wiley VCH Verlag GmbH amp Co KGaA ed Ullmann s Encyclopedia of Industrial Chemistry Weinheim Germany Wiley VCH Verlag GmbH amp Co KGaA pp 1 31 doi 10 1002 14356007 a04 405 pub2 ISBN 978 3 527 30673 2 retrieved 2022 03 04 PubChem Hazardous Substances Data Bank HSDB 622 pubchem ncbi nlm nih gov Retrieved 2022 03 04 a b Bolton Roger 2001 04 15 Allyl Bromide in John Wiley amp Sons Ltd ed Encyclopedia of Reagents for Organic Synthesis Chichester UK John Wiley amp Sons Ltd pp ra045 doi 10 1002 047084289x ra045 ISBN 978 0 471 93623 7 retrieved 2022 03 04 a b c Dagani M J Barda H J Benya T J Sanders D C Bromine Compounds Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a04 405 6 Chloro 1 Hexene and 8 Chloro 1 Octene Organic Syntheses 76 221 1999 doi 10 15227 orgsyn 076 0221 External links EditEntry at chemicalland21 com This article about an alkene is a stub You can help Wikipedia by expanding it vte This article about an organic halide is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Allyl bromide amp oldid 1117674488, wikipedia, wiki, book, books, library,
