Bromobenzene

Structural formula
General
Surname	Bromobenzene
other names	Monobromobenzene Phenyl bromide Bromobenzene
Molecular formula	C 6 H 5 Br
Brief description	colorless, aromatic-smelling liquid
External identifiers / databases
CAS number 108-86-1 EC number 203-623-8 ECHA InfoCard 100.003.295 PubChem 7961 Wikidata Q410597
properties
Molar mass	157.01 g mol −1
Physical state	liquid
density	1.50 g cm −3 (20 ° C)
Melting point	−31 ° C
boiling point	156 ° C
Vapor pressure	4.3 hPa (20 ° C) 8 hPa (30 ° C) 13 hPa (40 ° C) 25 hPa (50 ° C) 50 hPa (65 ° C)
solubility	very sparingly soluble in water (0.45 g l −1 at 30 ° C)
Dipole moment	1.70 (3) D (5.7 x 10 -30  C  ·  m )
Refractive index	1.5597 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 226-315-411 P: 273
Toxicological data	2380 mg kg −1 ( LD 50 ,  rat ,  oral )
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 The molecule is built up like benzene , one of the six hydrogen atoms in benzene has been replaced by a bromine atom.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.

${\displaystyle \mathrm {C_{6}H_{6}+Br_{2}\longrightarrow C_{6}H_{5}Br+HBr} }$

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

1. ↑ ^{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) .
2. ↑ 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.
3. ↑ 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.
4. ↑ 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 .
5. ↑ ^{a b} entry on bromobenzene. In: Römpp Online . Georg Thieme Verlag, accessed on May 15, 2014.
6. ↑ Joachim Buddrus: Fundamentals of Organic Chemistry , 4th edition, Walter de Gruyter Verlag, Berlin 2011, ISBN 978-3-11-024894-4 , pp. 375–376.
7. ↑ 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 .
8. ↑ 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 .
9. ↑ 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 .