1-Bromobutane

Names
Preferred IUPAC name 1-Bromobutane[1]
Other names Butyl bromide
Identifiers
CAS Number	109-65-9 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1098260
ChEMBL	ChEMBL160949 Y
ChemSpider	7711 Y
ECHA InfoCard	100.003.357
EC Number	203-691-9
MeSH	butyl+bromide
PubChem CID	8002
RTECS number	EJ6225000
UNII	SAV6Y78U3D Y
UN number	1126
CompTox Dashboard (EPA)	DTXSID6021903
InChI InChI=1S/C4H9Br/c1-2-3-4-5/h2-4H2,1H3 Y Key: MPPPKRYCTPRNTB-UHFFFAOYSA-N Y
SMILES CCCCBr
Properties
Chemical formula	C4H9Br
Molar mass	137.020 g·mol−1
Appearance	Colourless liquid
Density	1.2676 g mL−1
Melting point	−112.5 °C; −170.4 °F; 160.7 K
Boiling point	101.4 to 102.9 °C; 214.4 to 217.1 °F; 374.5 to 376.0 K
log P	2.828
Vapor pressure	5.3 kPa
Henry's law constant (kH)	140 nmol Pa kg−1
Refractive index (nD)	1.439
Thermochemistry
Heat capacity (C)	162.2 J K−1 mol−1
Std molar entropy (S⦵298)	327.02 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−148 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−2.7178–−2.7152 MJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H315, H319, H335, H411
Precautionary statements	P210, P261, P273, P305+P351+P338
Flash point	10 °C (50 °F; 283 K)
Autoignition temperature	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 compounds
Related alkanes	n-Propyl bromide 2-Bromopropane tert-Butyl bromide 2-Bromobutane 1-Bromohexane 2-Bromohexane 1-Bromododecane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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.

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.^[2]

1-Bromobutane can also be prepared from butanol by treatment with hydrobromic acid:^[3]

CH₃(CH₂)₃OH + HBr → CH₃(CH₂)₃Br + H₂O

Reactions

As a primary haloalkane, it is prone to S_N2 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, 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