1-Bromobutane

changed 477207128 1-bromobutane.svg skin-invert-image correct ?? 160 Skeletal formula of 1-bromobutane with some implicit hydrogens shown 1-bromobutane-3D-balls.png bg-transparent correct ?? 160 Ball and stick model of 1-bromobutane 1-Bromobutanebutyl bromide - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/8002 PubChem Compound National Center for Biotechnology Information 17 June 2012 USA 27 March 2005 Identification Butyl bromide 109-65-9 correct CAS BuBrn-BuBrnBuBrnBuBr correct FDA SAV6Y78U3D 8002 7711 correct chemspider 203-691-9 1126 butyl+bromide 160949 correct EBI 47231 correct EBI EJ6225000 1098260 CCCCBr 1S/C4H9Br/c1-2-3-4-5/h2-4H2,1H3 correct chemspider MPPPKRYCTPRNTB-UHFFFAOYSA-N correct chemspider 4 9 1 Colourless liquid 1.2676 g mL−1 160.7 374.5 to 376 2.828 5.3 kPa 140 nmol Pa kg−1 1.439 −148 kJ mol−1 −2.7178–−2.7152 MJ mol−1 327.02 J K−1 mol−1 162.2 J K−1 mol−1 flame exclamation mark environment DANGER 225 315 319 335 411 210 261 273 305+351+338 10 265 2.8–6.6% 2.761 g kg−1 (oral, rat) alkanes n-Propyl bromide 2-Bromopropane tert-Butyl bromide 2-Bromobutane 1-Bromohexane 2-Bromohexane 1-Bromododecane 1-Bromobutane is the organobromine compound with the formula C4H9Br 1 or CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide. Synthesis Most 1-bromoalkanes are prepared by free-radical addition of hydrogen bromide to the 1-alkene. These conditions lead to the anti-Markovnikov addition, i.e. give the 1-bromo derivatives. Dagani, M. J. Barda, H. J. Benya, T. J. Sanders, D. C. Bromine Compounds 10.1002/14356007.a04_405 1-Bromobutane can also be prepared from butanol by treatment with hydrobromic acid:Oliver Kamm, C. S. Marvel, R. H. Goshorn, Thomas Boyd, And E. F. Degering "Alkyl And Alkylene Bromides" Org. Synth. 1921, volume 1, p. 3. 10.15227/orgsyn.001.0003 free CH3(CH2)3OH + HBr → CH3(CH2)3Br + H2O Reactions As a primary haloalkane, it is prone to SN2 type reactions. It is commonly used as an alkylating agent. When combined with magnesium metal in dry ether, it gives the corresponding Grignard reagent. Such reagents are used to attach butyl groups to various substrates. 1-Bromobutane is the precursor to n-butyllithium:Brandsma, L. Verkraijsse, H. D. Preparative Polar Organometallic Chemistry I Springer-Verlag Berlin 1987 3-540-16916-4 2 Li + C4H9X → C4H9Li + LiX where X = Cl, Br The lithium for this reaction contains 1-3% sodium. When bromobutane is the precursor, the product is a homogeneous solution, consisting of a mixed cluster containing both LiBr and LiBu. 1-Fluorobutane can be obtained by reacting 1-bromobutane with potassium fluoride in ethylene glycol.Journal of the Chemical Society 1964 1322 1-Fluorobutane https://books.google.com/books?id=hMEg0eZvGMcC&pg=PA1322 6 August 2024 The Society en See also 1-Chlorobutane 1-Fluorobutane 1-Iodobutane References Category:Bromoalkanes Category:Alkylating agents