1-Bromobutane

1-Bromobutane

Names
IUPAC name 1-Bromobutane[1]
Other names Butyl bromide
Identifiers
CAS Number	109-65-9 Y
Beilstein Reference	1098260
ChEMBL	ChEMBL160949 Y
ChemSpider	7711 Y
EC Number	203-691-9
Jmol interactive 3D	Image
MeSH	butyl+bromide
PubChem	8002
RTECS number	EJ6225000
UN number	1126
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	137.02 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
Specific heat capacity (C)	162.2 J K−1 mol−1
Std molar entropy (So298)	327.02 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−148 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−2.7178–−2.7152 MJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H225, H315, H319, H335, H411
GHS precautionary statements	P210, P261, P273, P305+351+338
EU classification (DSD)	F Xi N
R-phrases	R11, R36/37/38, R40, R51/53
S-phrases	S16, S26
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 a primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.

Synthesis

It is prepared from butanol by treatment with hydrobromic acid]]:^[2]

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 is gives the corresponding Grignard reagent. Such reagents are used to attach butyl groups to various substrates.

1-Bromobutane is the precursor to n-butyllithium:^[3]

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