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2-Bromoacetonitrile

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Identification
Molecular formula
C2H2BrN
CAS number
590-17-0
IUPAC name
2-bromoacetonitrile
State
State

At room temperature, 2-Bromoacetonitrile is a liquid. It is typically handled as a liquid under standard conditions.

Melting point (Celsius)
-57.00
Melting point (Kelvin)
216.15
Boiling point (Celsius)
152.00
Boiling point (Kelvin)
425.15
General information
Molecular weight
118.95g/mol
Molar mass
118.9480g/mol
Density
1.5674g/cm3
Appearence

2-Bromoacetonitrile is typically a colorless to light yellow liquid. It may have an acrid odor associated with many organobromine compounds.

Comment on solubility

Solubility of 2-bromoacetonitrile

2-bromoacetonitrile, with the chemical formula C2H2BrN, showcases interesting solubility characteristics that are critical for its applications in organic synthesis and various chemical processes.

This compound exhibits the following solubility traits:

  • Polarity: The presence of the polar -CN group and the bromine atom on the carbon chain significantly increases the compound's polarity.
  • Solvent Compatibility: 2-bromoacetonitrile is typically soluble in polar solvents such as water, ethanol, and acetonitrile. This solubility is attributed to hydrogen bonding and dipole-dipole interactions.
  • Hydrophilicity: Its ability to interact with water makes it a suitable candidate for reactions in aqueous media.
  • Temperature Dependence: Solubility can also vary with temperature, often increasing in polar solvents as the temperature rises.

In summary, the solubility characteristics of 2-bromoacetonitrile are influenced by its molecular structure and the functional groups it contains. As stated, "The interplay between polarity and solvent nature is essential for understanding solubility." This makes it vital for chemists to consider the solvent's interactions when utilizing this compound in various applications.

Interesting facts

Interesting Facts about 2-Bromoacetonitrile

2-Bromoacetonitrile, known for its intriguing chemical properties, is a versatile compound in organic synthesis. Here are some fascinating insights:

  • Structure and Reactivity: The presence of both bromine and nitrile functional groups in 2-bromoacetonitrile makes it an excellent electrophile. This characteristic allows it to participate in various nucleophilic substitution reactions, forming valuable intermediates for pharmaceutical and agrochemical applications.
  • Applications: This compound is often used in the synthesis of α-amino acids and other biologically significant compounds. Its unique reactivity profile has made it a staple in the development of complex molecules, particularly in medicinal chemistry.
  • Safety Considerations: While working with 2-bromoacetonitrile, it is crucial to follow strict safety protocols. The compound is classified as toxic, and proper handling procedures should be in place to avoid inhalation or skin exposure.
  • Environmental Impact: Understanding how 2-bromoacetonitrile behaves in the environment is vital. Research shows it can undergo hydrolysis, leading to the formation of less harmful products, making it a candidate for greener chemical processes.

As a compound that bridges multiple fields in chemistry, 2-bromoacetonitrile continues to captivate researchers and students alike. Its multifaceted nature enhances the creative possibilities in the lab, yielding innovative solutions to complex problems.

Synonyms
BROMOACETONITRILE
590-17-0
2-bromoacetonitrile
Acetonitrile, bromo-
Cyanomethyl bromide
Bromomethyl cyanide
CCRIS 6213
EINECS 209-672-1
monobromoacetonitrile
BRN 0956569
DTXSID2021496
HSDB 8050
07K08J16VK
DTXCID001496
ACETONITRILE, 2-BROMO-
4-02-00-00531 (Beilstein Handbook Reference)
Acetonitrile, bromo
209-672-1
MFCD00001884
2-Bromoacetonitrile; Bromoacetonitrile; Bromomethyl cyanide
C2H2BrN
bromo acetonitrile
bromo-acetonitrile
bromacetonitrile
bromoacetonitile
UNII-07K08J16VK
bromo acetonitril
brornoacetonitrile
cyanomethylbromide
BrCH2CN
alpha-Bromoacetonitrile
2-bromanylethanenitrile
Bromoacetonitrile, 97%
SCHEMBL5742
CHEMBL2139477
Tox21_202207
AKOS005206906
CS-W020590
FB02517
NCGC00091440-01
NCGC00091440-02
NCGC00259756-01
AS-12053
CAS-590-17-0
InChI=1/C2H2BrN/c3-1-2-4/h1H
Bromoacetonitrile, purum, >=97.0% (GC)
DB-022975
B1058
NS00006186
EN300-67455
D88745
A832108
Q27236310
F1905-7004