Misplaced Pages

Bromoethane

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Not to be confused with Ethidium bromide.
Bromoethane
Skeletal formula of bromoethane
Skeletal formula of bromoethane
Skeletal formula of bromoethane with all explicit hydrogens added
Skeletal formula of bromoethane with all explicit hydrogens added
Ball and stick model of bromoethane
Ball and stick model of bromoethane
Spacefill model of bromoethane
Spacefill model of bromoethane
Names
Preferred IUPAC name Bromoethane
Other names Ethyl bromide
Monobromoethane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1209224
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.751 Edit this at Wikidata
EC Number
  • 200-825-8
KEGG
MeSH bromoethane
PubChem CID
RTECS number
  • KH6475000
UNII
UN number 1891
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H5Br/c1-2-3/h2H2,1H3Key: RDHPKYGYEGBMSE-UHFFFAOYSA-N
SMILES
  • CCBr
Properties
Chemical formula C2H5Br
Molar mass 108.966 g·mol
Appearance Colorless liquid
Odor ether-like
Density 1.46 g mL
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 kg
Magnetic susceptibility (χ) -54.70·10 cm/mol
Refractive index (nD) 1.4225
Viscosity 402 Pa.s (at 20 °C)
Thermochemistry
Heat capacity (C) 105.8 J K mol
Std enthalpy of
formation (ΔfH298) 		−97.6–93.4 kJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS06: Toxic GHS08: Health hazard
Signal word Danger
Hazard statements H225, H302, H332, H351
Precautionary statements P210, P281
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 (oral, rat)
LC50 (median concentration) 26,980 ppm (rat, 1 hr)
16,230 ppm (mouse, 1 hr)
4681 ppm (rat)
2723 ppm (mouse)
LCLo (lowest published) 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/m)
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0265". National Institute for Occupational Safety and Health (NIOSH).
  2. "bromoethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 15 June 2012.
  3. ^ "Ethyl bromide". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. Oliver Kamm & C. S. Marvel (1941). "Alkyl and alkylene bromides". Organic Syntheses; Collected Volumes, vol. 1, p. 25.
  5. Makosza, M.; Jonczyk, A. "Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile". Organic Syntheses. 55: 91; Collected Volumes, vol. 6, p. 897.
  6. Petit, Y.; Larchevêque, M. "Ethyl Glycidate from (S)-Serine: Ethyl (R)-(+)-2,3-Epoxypropanoate". Organic Syntheses. 75: 37; Collected Volumes, vol. 10, p. 401.
  7. E. Brand; Brand, F. C. "Guanidodacetic Acid". Organic Syntheses. 22: 440; Collected Volumes, vol. 3.
  8. Brasen, W. R; Hauser, C. R. "o-Methylethylbenzyl Alcohol". Organic Syntheses. 34: 58; Collected Volumes, vol. 4, p. 582.

External links

Categories: