Bromoethane

Names
Preferred IUPAC name Bromoethane[2]
Other names Ethyl bromide[1] Monobromoethane[1]
Identifiers
CAS Number	74-96-4 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1209224
ChEBI	CHEBI:47232
ChEMBL	ChEMBL156378 Y
ChemSpider	6092 Y
ECHA InfoCard	100.000.751
EC Number	200-825-8
KEGG	C19354 N
MeSH	bromoethane
PubChem CID	6332
RTECS number	KH6475000
UNII	LI8384T9PH Y
UN number	1891
CompTox Dashboard (EPA)	DTXSID6020199
InChI InChI=1S/C2H5Br/c1-2-3/h2H2,1H3 Y Key: RDHPKYGYEGBMSE-UHFFFAOYSA-N Y
SMILES CCBr
Properties
Chemical formula	C2H5Br
Molar mass	108.966 g·mol−1
Appearance	Colorless liquid
Odor	ether-like
Density	1.46 g mL−1
Melting point	−120 to −116 °C; −184 to −177 °F; 153 to 157 K
Boiling point	38.0 to 38.8 °C; 100.3 to 101.8 °F; 311.1 to 311.9 K
Solubility in water	1.067 g/100 mL (0 °C) 0.914 g/100 mL (20 °C) 0.896 g/100 mL (30 °C)
Solubility	miscible with ethanol, ether, chloroform, organic solvents
log P	1.809
Vapor pressure	51.97 kPa (at 20 °C)
Henry's law constant (kH)	1.3 μmol Pa−1 kg−1
Magnetic susceptibility (χ)	-54.70·10−6 cm3/mol
Refractive index (nD)	1.4225
Viscosity	402 Pa.s (at 20 °C)
Thermochemistry
Heat capacity (C)	105.8 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−97.6–93.4 kJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H332, H351
Precautionary statements	P210, P281
NFPA 704 (fire diamond)	3 1 0
Flash point	−23 °C (−9 °F; 250 K)
Autoignition temperature	511 °C (952 °F; 784 K)
Explosive limits	6.75–11.25%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	1.35 g kg−1 (oral, rat)
LC50 (median concentration)	26,980 ppm (rat, 1 hr) 16,230 ppm (mouse, 1 hr) 4681 ppm (rat) 2723 ppm (mouse)[3]
LCLo (lowest published)	3500 ppm (mouse) 24,000 ppm (guinea pig, 30 min) 7000 ppm (guinea pig, >4.5 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 200 ppm (890 mg/m3)[1]
REL (Recommended)	None established[1]
IDLH (Immediate danger)	2000 ppm[1]
Related compounds
Related alkanes	Bromomethane Bromoiodomethane n-Propyl bromide 2-Bromopropane tert-Butyl bromide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide). This volatile compound has an ether-like odor.

Preparation

The preparation of EtBr stands as a model for the synthesis of bromoalkanes in general. It is usually prepared by the addition of hydrogen bromide to ethene:

H₂C=CH₂ + HBr → H₃C-CH₂Br

Bromoethane is inexpensive and would rarely be prepared in the laboratory. A laboratory synthesis includes reacting ethanol with a mixture of hydrobromic and sulfuric acids. An alternate route involves refluxing ethanol with phosphorus and bromine; phosphorus tribromide is generated in situ.^[4]

Uses

In organic synthesis, EtBr is the synthetic equivalent of the ethyl carbocation (Et⁺) synthon.^[5] In reality, such a cation is not actually formed. For example, carboxylates salts are converted to ethyl esters,^[6] carbanions to ethylated derivatives, thiourea into ethylisothiouronium salts,^[7] and amines into ethylamines.^[8]

Safety

Short chain monohalocarbons in general are potentially dangerous alkylating agents. Bromides are better alkylating agents than chlorides, thus exposure to them should be minimized. EtBr is classified by the State of California as carcinogenic and a reproductive toxin.^{[citation needed]}