Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1-Bromobutane: Difference between pages

| Watchedfields = changed

| verifiedrevid = 477207128

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 160

| ImageName = Skeletal formula of 1-bromobutane with some implicit hydrogens shown

| ImageFile1 = 1-bromobutane-3D-balls.png

| ImageFile1_Ref = {{chemboximage|correct|??}}

| ImageSize1 = 160

| ImageName1 = Ball and stick model of 1-bromobutane

| PIN = 1-Bromobutane<ref>{{cite web|title=butyl bromide - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8002|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=17 June 2012|location=USA|date=27 March 2005|at=Identification}}</ref>

| OtherNames = Butyl bromide

|Section1={{Chembox Identifiers

| CASNo = 109-65-9

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = SAV6Y78U3D

| ChemSpiderID = 7711

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 203-691-9

| UNNumber = 1126

| MeSHName = butyl+bromide

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| RTECS = EJ6225000

| Beilstein = 1098260

| SMILES = CCCCBr

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=4 | H=9 | Br=1

| Appearance = Colourless liquid

| Density = 1.2676 g mL⁻¹

| MeltingPtK = 160.7

| BoilingPtK = 374.5 to 376

| LogP = 2.828

| VaporPressure = 5.3 kPa

| HenryConstant = 140 nmol Pa kg⁻¹

| RefractIndex = 1.439

}}

|Section3={{Chembox Thermochemistry

| DeltaHf = −148 kJ mol⁻¹

| DeltaHc = −2.7178–−2.7152 MJ mol⁻¹

| Entropy = 327.02 J K⁻¹ mol⁻¹

| HeatCapacity = 162.2 J K⁻¹ mol⁻¹

}}

|Section4={{Chembox Hazards

| GHSPictograms = {{gHS flame}} {{gHS exclamation mark}} {{gHS environment}}

| GHSSignalWord = '''DANGER'''

| HPhrases = {{h-phrases|225|315|319|335|411}}

| PPhrases = {{p-phrases|210|261|273|305+351+338}}

| FlashPtC = 10

| AutoignitionPtC = 265

| ExploLimits = 2.8–6.6%

| LD50 = 2.761 g kg⁻¹ <small>(oral, rat)</small>

}}

|Section5={{Chembox Related

| OtherFunction_label = alkanes

| OtherFunction = {{unbulleted list|[[n-Propyl bromide|''n''-Propyl bromide]]|[[2-Bromopropane]]|[[tert-Butyl bromide|''tert''-Butyl bromide]]|[[2-Bromobutane]]|[[1-Bromohexane]]|[[2-Bromohexane]]|[[1-Bromododecane]]}}

'''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 solvent]]s. 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.<ref name=Ullmann>{{ Ullmann | author = Dagani, M. J. | author2 = Barda, H. J. | author3 = Benya, T. J. | author4 = Sanders, D. C. | title = Bromine Compounds | doi = 10.1002/14356007.a04_405 }}</ref>

1-Bromobutane can also be prepared from [[butanol]] by treatment with [[hydrobromic acid]]:<ref>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}}</ref>

:CH₃(CH₂)₃OH + HBr → CH₃(CH₂)₃Br + H₂O

==Reactions==

As a primary [[haloalkane]], it is prone to [[SN2 reaction|S_N2]] type reactions. It is commonly used as an [[alkylating agent]]. When combined with [[magnesium]] metal in dry [[diethyl ether|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|''n''-butyllithium]]:<ref>{{cite book |author1=Brandsma, L. |author2=Verkraijsse, H. D. | title = Preparative Polar Organometallic Chemistry I | publisher = [[Springer-Verlag]] | location = Berlin | year = 1987 | isbn = 3-540-16916-4}}</ref>

: 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.

==References==

{{reflist}}

{{DEFAULTSORT:Bromobutane, 1-}}

[[Category:Bromoalkanes]]

[[Category:Alkylating agents]]