2-Bromopentane
{{Chembox
| Reference =
| SystematicName =
| OtherNames = 2-Pentyl bromide
| data page pagename =
| ImageFile = 2-Brompentan.svg
| ImageSize = 200px
| ImageName = Skeletal formula of 2-bromopentane
| ImageFileL1 = R-2-bromopentane vdw.png
| ImageSizeL1 = 150px
| ImageNameL1 = Van der Waals space filling structure of (R)-2-bromopentane
| ImageCaptionL1 = (R)-2-bromopentane
| ImageFileR1 = S-2-bromopentane vdw.png
| ImageSizeR1 = 150px
| ImageNameR1 = Van der Waals space filling structure of (S)-2-bromopentane
| ImageCaptionR1 = (S)-2-bromopentane
| Section1 = {{Chembox Identifiers
| CASNo = 107-81-3
| CASNo_Comment =
| CASNoOther =
| CASNo1 = 29117-44-0
| CASNo1_Comment = (R)
| CASNo2 = 29882-58-4
| CASNo2_Comment = (S)
| ChEBI =
| EINECS = 203-521-3
| Gmelin =
| InChI = 1S/C5H11Br/c1-3-4-5(2)6/h5H,3-4H2,1-2H3
| InChIKey = LGAJYTCRJPCZRJ-UHFFFAOYSA-N
| KEGG =
| MeSHName =
| PubChem = 7890
| PubChem1 = 71446854
| PubChem1_Comment = (R)
| PubChem2 = 24884213
| PubChem2_Comment = (S)
| ChemSpiderID = 7602
| ChemSpiderID1 = 60603465
| ChemSpiderID1_Comment = (R)
| ChemSpiderID2 = 21427355
| ChemSpiderID2_Comment = (S)
| RTECS =
| SMILES = CCCC(C)Br
| UNNumber = 2343
}}
| Section2 = {{Chembox Properties
| C = 5 | H = 11 | Br = 1
| Appearance = colorless liquid
| BoilingPtK = 390.4
| Density = 1.208 g mL−1
| MeltingPtK =
| VaporPressure = 2.84 kPa
}}
| Section7 = {{Chembox Hazards
| FlashPtK = 293.7
| LD50 =
| LC50 =
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-I =
| NFPA-S =
| PEL =
| REL =
| ExternalSDS =
| GHSPictograms = {{GHS02}}{{GHS07}}
| GHSSignalWord =
| HPhrases = {{H-phrases|H225|H226|H315|H319|H335}}
| PPhrases = {{P-phrases|P210|P233|P240|P241|P242|P243|P261|P264|P264+265|P271|P280|P302+P352|P303+361+353|P304+P340|P305+P351+P338|P319|P321|P332+P317|P337+P317|P362+P364|P370+P378|P403+P235|P405|P501}}
}}
}}
2-Bromopentane is a bromoalkane and isomer of bromopentane. It is a colorless liquid. 2-Bromopentane is chiral and thus can be obtained as either of two stereoisomers designated as (R)-2-bromopentane and (S)-2-bromopentane, or as a racemic 1:1 mixture of the two enantiomers.
Applications
2-Bromopentane is an organic synthetic compound that can be used in cross-coupling reactions.{{Cite journal |last=Cahiez |first=Gérard |last2=Moyeux |first2=Alban |date=2010-03-10 |title=Cobalt-Catalyzed Cross-Coupling Reactions |url=https://pubs.acs.org/doi/10.1021/cr9000786 |journal=Chemical Reviews |language=en |volume=110 |issue=3 |pages=1435–1462 |doi=10.1021/cr9000786 |issn=0009-2665}} It is also used as an intermediate in organic synthesis.{{Cite journal |last=Ekpa |first=O. |last2=Wheeler |first2=J.W. |last3=Cokendolpher |first3=J.C. |last4=Duffield |first4=R.M. |date=1985 |title=Ketones and alcohols in the defensive secretion of Leiobunum townsendi weed and a review of the known exocrine secretions of Palpatores (Arachnida:Opiliones) |url=https://linkinghub.elsevier.com/retrieve/pii/0305049185903657 |journal=Comparative Biochemistry and Physiology Part B: Comparative Biochemistry |language=en |volume=81 |issue=3 |pages=555–557 |doi=10.1016/0305-0491(85)90365-7}}
Synthesis
2-Bromopentane, along with 3-bromopentane, may be produced by the bromination of 2-pentanol. This has historically been performed using hydrogen bromide gas, aqueous sulfuric and hydrobromic acid mixtures, and phosphorus tribromide.{{Cite journal |last=Howell |first=B. A. |last2=Kohrman |first2=R. E. |date=October 1984 |title=Preparation of 2-Bromopentane |url=https://pubs.acs.org/doi/pdf/10.1021/ed061p932?casa_token=qZy_8PNRgNoAAAAA:zcaOqKS-o3oqLYZputSXhNGoliqQhPN8Kw6syYacKDVI72a-tXcbbOBkcBvCsBTPujvOiJQ_IPwXxUQc |journal=Journal of Chemical Education |volume=61 |issue=10 |doi=10.1021/ed061p932}}