1-Bromobutane is the organobromine compound with the formula 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.
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.[2]
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.
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.
Referencesedit
^"butyl bromide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 17 June 2012.
^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. doi:10.15227/orgsyn.001.0003
bromobutane, organobromine, compound, with, formula, colorless, liquid, although, impure, samples, appear, yellowish, insoluble, water, soluble, organic, solvents, primarily, used, source, butyl, group, organic, synthesis, several, isomers, butyl, bromide, nam. 1 Bromobutane is the organobromine compound with the formula 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 1 Bromobutane NamesPreferred IUPAC name 1 Bromobutane 1 Other names Butyl bromideIdentifiersCAS Number 109 65 9 Y3D model JSmol Interactive imageBeilstein Reference 1098260ChEMBL ChEMBL160949 YChemSpider 7711 YECHA InfoCard 100 003 357EC Number 203 691 9MeSH butyl bromidePubChem CID 8002RTECS number EJ6225000UNII SAV6Y78U3D YUN number 1126CompTox Dashboard EPA DTXSID6021903InChI InChI 1S C4H9Br c1 2 3 4 5 h2 4H2 1H3 YKey MPPPKRYCTPRNTB UHFFFAOYSA N YSMILES CCCCBrPropertiesChemical formula C 4H 9BrMolar mass 137 020 g mol 1Appearance Colourless liquidDensity 1 2676 g mL 1Melting point 112 5 C 170 4 F 160 7 KBoiling point 101 4 to 102 9 C 214 4 to 217 1 F 374 5 to 376 0 Klog P 2 828Vapor pressure 5 3 kPaHenry s lawconstant kH 140 nmol Pa kg 1Refractive index nD 1 439ThermochemistryHeat capacity C 162 2 J K 1 mol 1Std molarentropy S 298 327 02 J K 1 mol 1Std enthalpy offormation DfH 298 148 kJ mol 1Std enthalpy ofcombustion DcH 298 2 7178 2 7152 MJ mol 1HazardsGHS labelling PictogramsSignal word DangerHazard statements H225 H315 H319 H335 H411Precautionary statements P210 P261 P273 P305 P351 P338Flash point 10 C 50 F 283 K Autoignitiontemperature 265 C 509 F 538 K Explosive limits 2 8 6 6 Lethal dose or concentration LD LC LD50 median dose 2 761 g kg 1 oral rat Related compoundsRelated alkanes n Propyl bromide2 Bromopropanetert Butyl bromide2 Bromobutane1 Bromohexane2 Bromohexane1 BromododecaneExcept 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 referencesSynthesis editMost 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 2 1 Bromobutane can also be prepared from butanol by treatment with hydrobromic acid 3 CH3 CH2 3OH HBr CH3 CH2 3Br H2OReactions editAs 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 4 2 Li C4H9X C4H9Li LiX where X Cl BrThe 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 References edit butyl bromide Compound Summary PubChem Compound USA National Center for Biotechnology Information 27 March 2005 Identification Retrieved 17 June 2012 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 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 doi 10 15227 orgsyn 001 0003 Brandsma L Verkraijsse H D 1987 Preparative Polar Organometallic Chemistry I Berlin Springer Verlag ISBN 3 540 16916 4 Retrieved from https en wikipedia org w index php title 1 Bromobutane amp oldid 1177366094, wikipedia, wiki, book, books, library,
