2-Bromopentane

2-Bromopentane

Skeletal formula of 2-bromopentane
Van der Waals space filling structure of (R)-2-bromopentane (R)-2-bromopentane Van der Waals space filling structure of (S)-2-bromopentane (S)-2-bromopentane
Names
Preferred IUPAC name 2-Bromopentane [1]
Other names 2-Pentyl bromide
Identifiers
CAS Number	107-81-3 29117-44-0 (R) 29882-58-4 (S)
3D model (JSmol)	Interactive image
ChemSpider	7602 60603465 (R) 21427355 (S)
ECHA InfoCard	100.003.202
EC Number	203-521-3
PubChem CID	7890 71446854  (R) 24884213  (S)
UN number	2343
CompTox Dashboard (EPA)	DTXSID90870456
InChI InChI=1S/C5H11Br/c1-3-4-5(2)6/h5H,3-4H2,1-2H3 Key: LGAJYTCRJPCZRJ-UHFFFAOYSA-N
SMILES CCCC(C)Br
Properties
Chemical formula	C5H11Br
Molar mass	151.047 g·mol−1
Appearance	colorless liquid
Density	1.208 g mL−1
Boiling point	117.3 °C; 243.0 °F; 390.4 K
Vapor pressure	2.84 kPa
Hazards
GHS labelling:
Pictograms
Hazard statements	H225, H226, H315, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, P405, P501
Flash point	20.6 °C; 69.0 °F; 293.7 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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. ^[2] It is also used as an intermediate in organic synthesis. ^[3]

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. ^[4]

References

1. "2-Bromopentane". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 28 December 2023.
2. Cahiez, Gérard; Moyeux, Alban (2010-03-10). "Cobalt-Catalyzed Cross-Coupling Reactions" . Chemical Reviews. 110 (3): 1435–1462. doi:10.1021/cr9000786. ISSN   0009-2665.
3. Ekpa, O.; Wheeler, J.W.; Cokendolpher, J.C.; Duffield, R.M. (1985). "Ketones and alcohols in the defensive secretion of Leiobunum townsendi weed and a review of the known exocrine secretions of Palpatores (Arachnida:Opiliones)" . Comparative Biochemistry and Physiology Part B: Comparative Biochemistry. 81 (3): 555–557. doi:10.1016/0305-0491(85)90365-7.
4. Howell, B. A.; Kohrman, R. E. (October 1984). "Preparation of 2-Bromopentane" . Journal of Chemical Education . 61 (10). doi:10.1021/ed061p932.