Bromobenzene
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Bromobenzene | |||||||||||||||
other names |
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Molecular formula | C 6 H 5 Br | |||||||||||||||
Brief description |
colorless, aromatic-smelling liquid |
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properties | ||||||||||||||||
Molar mass | 157.01 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
1.50 g cm −3 (20 ° C) |
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Melting point |
−31 ° C |
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boiling point |
156 ° C |
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Vapor pressure |
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solubility |
very sparingly soluble in water (0.45 g l −1 at 30 ° C) |
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Dipole moment | ||||||||||||||||
Refractive index |
1.5597 (20 ° C) |
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safety instructions | ||||||||||||||||
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Toxicological data | ||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
Bromobenzene is an aromatic halogenated hydrocarbon . The molecule is built up like benzene , one of the six hydrogen atoms in benzene has been replaced by a bromine atom.
presentation
Bromobenzene can be produced from benzene and bromine by electrophilic substitution on the aromatic.
As a rule, Lewis acids such as aluminum bromide (AlBr 3 ) or iron tribromide (FeBr 3 ) are used as the catalyst .
properties
Physical Properties
Bromobenzene is a colorless, flammable liquid with a typical odor. The boiling point is 156 ° C at normal pressure . According to Antoine, the vapor pressure function results from log 10 (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.072025, B = 1495.044 and C = −61.508 in the temperature range from 329.2 K to 427.4 K. It is largely non-polar, therefore insoluble in water, soluble in alcohols , benzene , chloroform and ethers . Bromobenzene is not very volatile; the vapors are much heavier than air.
Safety-related parameters
Bromobenzene forms flammable vapor-air mixtures above the flash point. The compound has a flash point of 51 ° C. The explosion range is between 0.5% by volume as the lower explosion limit (LEL) and 2.5% by volume as the upper explosion limit (UEL). The ignition temperature is 565 ° C. The substance therefore falls into temperature class T1. The electrical conductivity is rather low at 1.2 · 10 −9 S · m −1 .
use
Bromobenzene is used as a solvent and as a starting material for chemical syntheses. It is a popular base for Grignard compounds such as phenyl magnesium bromide .
safety instructions
- Inhalation or swallowing can be harmful to health
- Can irritate and damage the respiratory tract, digestive tract, eyes and skin, leading to difficulty breathing and loss of consciousness
Individual evidence
- ↑ a b c d e f g h i j k l m n o p Entry on bromobenzene in the GESTIS substance database of the IFA , accessed on April 11, 2018(JavaScript required) .
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dipole Moments, pp. 9-53.
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-58.
- ↑ Entry on bromobenzene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ a b entry on bromobenzene. In: Römpp Online . Georg Thieme Verlag, accessed on May 15, 2014.
- ↑ Joachim Buddrus: Fundamentals of Organic Chemistry , 4th edition, Walter de Gruyter Verlag, Berlin 2011, ISBN 978-3-11-024894-4 , pp. 375–376.
- ↑ Ramanjaneyulu, K .; Surendranath, KN; Krishnaiah, A .: Excess volumes of binary mixtures of trichlorethylene with some aliphatic, alicyclic and aromatic hydrocarbons in Fluid Phase Equilib. 44 (1989) 357-361, doi : 10.1016 / 0378-3812 (89) 80062-7 .
- ↑ Dreyer, R .; Martin, W .; von Weber, U .: The saturation vapor pressures of benzene, toluene, ethylbenzene, styrene, cumene and bromobenzene between 10 and 760 Torr in J. Prakt. Chem. 1 (1955) 324-328, doi : 10.1002 / prac.19550010508 .
- ↑ Technical rule for hazardous substances TRGS 727, BG RCI leaflet T033 Avoidance of ignition hazards due to electrostatic charges , status August 2016, Jedermann-Verlag Heidelberg, ISBN 978-3-86825-103-6 .