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Bromoethane

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Bromoethane
Skeletal formula of bromoethane
Skeletal formula of bromoethane with all explicit hydrogens added
Ball and stick model of bromoethane
Spacefill model of bromoethane
Names
Preferred IUPAC name
Bromoethane
Other names
Ethyl bromide
Monobromoethane
Identifiers
3D model (JSmol)
1209224
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.751
EC Number
  • 200-825-8
KEGG
MeSH bromoethane
PubChem CID
RTECS number
  • KH6475000
UNII
UN number 1891
  • InChI=1S/C2H5Br/c1-2-3/h2H2,1H3 checkY
    Key: RDHPKYGYEGBMSE-UHFFFAOYSA-N checkY
  • CCBr
Properties
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
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)
1.3 μmol Pa−1 kg−1
-54.70·10−6 cm3/mol
1.4225
Viscosity 402 Pa.s (at 20 °C)
Thermochemistry
105.8 J K−1 mol−1
−97.6–93.4 kJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS06: Toxic GHS08: Health hazard
Danger
H225, H302, H332, H351
P210, P281
NFPA 704 (fire diamond)
3
1
0
Flash point −23 °C (−9 °F; 250 K)
511 °C (952 °F; 784 K)
Explosive limits 6.75–11.25%
Lethal dose or concentration (LD, LC):
1.35 g kg−1(oral, rat)
26,980 ppm (rat, 1 hr)
16,230 ppm (mouse, 1 hr)
4681 ppm (rat)
2723 ppm (mouse)
3500 ppm (mouse)
24,000 ppm (guinea pig, 30 min)
7000 ppm (guinea pig, >4.5 hr)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 200 ppm (890 mg/m3)
REL (Recommended)
None established
IDLH (Immediate danger)
2000 ppm
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.

Uses

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

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.

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