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Benzyl bromide

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Identification
Molecular formula
C8H9Br
CAS number
100-39-0
IUPAC name
1-(bromomethyl)-3-methyl-benzene
State
State

At room temperature, benzyl bromide is a liquid. It is important to handle it with care due to its reactive nature and irritating vapors.

Melting point (Celsius)
-3.00
Melting point (Kelvin)
270.15
Boiling point (Celsius)
201.80
Boiling point (Kelvin)
474.95
General information
Molecular weight
171.04g/mol
Molar mass
171.0380g/mol
Density
1.4388g/cm3
Appearence

Benzyl bromide appears as a colorless to slightly yellow liquid. It has a sharp, penetrating odor and is known for causing tears in the eyes due to its lachrymatory properties.

Comment on solubility

Solubility of 1-(Bromomethyl)-3-methyl-benzene

The solubility of 1-(bromomethyl)-3-methyl-benzene, also known as o-bromotoluene, tends to be influenced by a variety of factors including temperature, the presence of solvents, and the chemical structure of the compound itself. Generally, this compound exhibits the following characteristics in terms of solubility:

  • Polar vs. Nonpolar Solvents: 1-(bromomethyl)-3-methyl-benzene is primarily nonpolar. Therefore, it tends to dissolve more readily in nonpolar solvents such as hexane or toluene, while its solubility in polar solvents like water is significantly limited.
  • Temperature Effects: Increased temperature can enhance the solubility of organic compounds. For 1-(bromomethyl)-3-methyl-benzene, higher temperatures may result in increased dispersion, leading to a higher solubility in compatible organic solvents.
  • Structural Influence: The presence of a bromine atom can impart certain polar characteristics, yet it remains predominantly hydrophobic due to the alkyl and aromatic portions of the molecule. This unique structure allows it to exhibit distinctive solubility behavior.

In summary, when considering the solubility of 1-(bromomethyl)-3-methyl-benzene, it is crucial to note:

  1. It is poorly soluble in water.
  2. Better solubility is expected in non-polar organic solvents.
  3. Temperature and solvent choice play significant roles in its solubility behavior.

Overall, understanding the solubility of this compound is vital for various applications in chemical synthesis and industrial processes.

Interesting facts

Interesting Facts about 1-(Bromomethyl)-3-methyl-benzene

1-(Bromomethyl)-3-methyl-benzene, often referred to as a derivative of toluene, is a fascinating compound that offers several intriguing aspects worth exploring:

  • Structure and Reactivity: This compound features a bromomethyl group, which makes it a useful intermediate in various chemical syntheses. The presence of the bromine atom enhances its reactivity, allowing it to participate in nucleophilic substitution reactions.
  • Applications in Organic Synthesis: Due to its unique functional groups, 1-(Bromomethyl)-3-methyl-benzene is employed in synthesizing pharmaceuticals and agrochemicals. As a building block, it can help create more complex molecules that are vital in various applications.
  • Synthesis Pathways: There are several methods for synthesizing this compound, but one noteworthy approach involves the bromination of toluene, followed by specific regioselective reactions that allow for the introduction of the bromomethyl group.
  • Research Significance: Researchers often study this compound to understand reaction mechanisms involving benzene derivatives. Its behavior in electrophilic aromatic substitution reactions provides insights into the electronic effects of substituents on aromatic systems.
  • Chemical Safety: As with many halogenated compounds, caution is advised when handling 1-(Bromomethyl)-3-methyl-benzene due to its potential hazards. Protective measures should be taken to avoid exposure, as brominated compounds can be toxic and hazardous.

In summary, the multifaceted nature of 1-(Bromomethyl)-3-methyl-benzene combined with its applications in organic chemistry makes it an important compound worthy of study. As the field of organic synthesis continues to evolve, this compound will remain relevant in the development of new and innovative chemical entities.

Synonyms
3-Methylbenzyl bromide
1-(Bromomethyl)-3-methylbenzene
alpha-Bromo-m-xylene
M-XYLYL BROMIDE
Benzene, 1-(bromomethyl)-3-methyl-
.alpha.-Bromo-m-xylene
a-bromo-m-xylene
3-bromomethyltoluene
HSDB 2191
EINECS 210-625-2
UNII-U49150ER3L
AI3-20884
U49150ER3L
NSC-60146
M-XYLYL BROMIDE [MI]
DTXSID1060716
FWLWTILKTABGKQ-UHFFFAOYSA-
alphaBromomxylene
mXylene, alphabromo
mMethylbenzyl bromide
3methylbenzyl bromide
omega-Bromo-m-xylene
3(bromomethyl)toluene
1(Bromomethyl)3methylbenzene
3-bromomethyl-1-methylbenzene
Benzene, 1(bromomethyl)3methyl
DTXCID6043202
UN1701
fwlwtilktabgkq-uhfffaoysa-n
inchi=1/c8h9br/c1-7-3-2-4-8(5-7)6-9/h2-5h,6h2,1h3
620-13-3
3-(Bromomethyl)toluene
m-Methylbenzyl bromide
m-Xylene, .alpha.-bromo-
MFCD00000177
NSC 60146
1-Bromomethyl-3-methyl-benzene
3-methylbenzylbromide
m-Xylene, alpha-bromo-
1-(Bromomethyl)-3-Methyl-Benzene
m-Xylylbromid
1-(Bromomethyl)-3-methylbenzene; 3-Methylbenzyl Bromide; NSC 60146; m-Methylbenzyl Bromide; m-Xylyl Bromide; a-Bromo-m-xylene
m-methylbenzylbromide
|A-Bromo-m-xylene
3-methyl benzylbromide
m-(Bromomethyl)toluene
3-methyl benzyl bromide
3-methyl-benzyl bromide
1-Bromomethyl-3-methylbenzene
SCHEMBL177507
3-Methylbenzyl bromide, 96%
NSC60146
AKOS000446926
PS-10047
SY014863
DB-016167
B1010
B3585
NS00034885
A833533
Q27290667