Bromoethane

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Bromoethane
Skeletal formula of bromoethane Bromoethane.png
Skeletal formula of bromoethane
Skeletal formula of bromoethane with all explicit hydrogens added Bromethan.svg
Skeletal formula of bromoethane with all explicit hydrogens added
Ball and stick model of bromoethane Bromoethane-3D-balls.png
Ball and stick model of bromoethane
Spacefill model of bromoethane Bromoethane-3D-vdW.png
Spacefill model of bromoethane
Names
Preferred IUPAC name
Bromoethane [1]
Other names
Ethyl bromide [2]
Monobromoethane [2]
Identifiers
3D model (JSmol)
1209224
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.751 OOjs UI icon edit-ltr-progressive.svg
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 Yes check.svgY
    Key: RDHPKYGYEGBMSE-UHFFFAOYSA-N Yes check.svgY
  • CCBr
Properties
C2H5Br
Molar mass 108.966 g·mol−1
AppearanceColorless 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:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
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) [3]
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) [2]
REL (Recommended)
None established [2]
IDLH (Immediate danger)
2000 ppm [2]
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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 ]

Related Research Articles

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<span class="mw-page-title-main">Ethanethiol</span> Chemical compound

Ethanethiol, commonly known as ethyl mercaptan, is an organosulfur compound with the formula CH3CH2SH. is a colorless liquid with a distinct odor. Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with sulfur in place of oxygen. The odor of EtSH is infamous. Ethanethiol is more volatile than ethanol due to a diminished ability to engage in hydrogen bonding. Ethanethiol is toxic in high concentrations. It occurs naturally as a minor component of petroleum, and may be added to otherwise odorless gaseous products such as liquefied petroleum gas (LPG) to help warn of gas leaks. At these concentrations, ethanethiol is not harmful.

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Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.

<span class="mw-page-title-main">Allyl chloride</span> Chemical compound

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<span class="mw-page-title-main">Hydrogen bromide</span> Chemical compound

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<span class="mw-page-title-main">Ethyl acetate</span> Chemical compound

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

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<span class="mw-page-title-main">Phosphorus pentachloride</span> Chemical compound

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<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

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<span class="mw-page-title-main">Arsenic trichloride</span> Chemical compound

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<span class="mw-page-title-main">Dimethoxymethane</span> Chemical compound

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<span class="mw-page-title-main">Copper(I) bromide</span> Chemical compound

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<span class="mw-page-title-main">Propargyl bromide</span> Chemical compound

Propargyl bromide, also known as 3-bromo-prop-1-yne, is an organic compound with the chemical formula HC≡CCH2Br. A colorless liquid, it is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is used as a reagent in organic synthesis.

References

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