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Diazomethane

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Identification
Molecular formula
CH2N2
CAS number
334-88-3
IUPAC name
diazomethane
State
State
Diazomethane is a gas at room temperature, and it is highly explosive. It is typically generated in situ in a laboratory setting due to its instability.
Melting point (Celsius)
-145.00
Melting point (Kelvin)
128.15
Boiling point (Celsius)
-23.00
Boiling point (Kelvin)
250.15
General information
Molecular weight
42.04g/mol
Molar mass
42.0410g/mol
Density
0.0014g/cm3
Appearence

Diazomethane is typically found as a pale yellow gas. In solution, it can appear yellow due to its inherent pigment. It has a notably foul, irritating odor and is known for its explosive nature, specifically when exposed to rough conditions or mixed with other chemicals.

Comment on solubility

Solubility of Diazomethane

Diazomethane, with the chemical formula CH2N2, is a fascinating compound known for its distinctive properties, particularly regarding its solubility. Here are some key points regarding its solubility:

  • Solvent Interaction: Diazomethane is generally soluble in organic solvents, such as ether, acetone, and hexane. This makes it particularly useful in organic synthesis where non-polar solvents are often employed.
  • Water Solubility: One notable aspect of diazomethane is that it is insoluble in water. This is primarily due to its low polarity and the inability of water molecules to stabilize the diazo group present in the molecule.
  • Temperature Effects: The solubility of diazomethane can be influenced by temperature, with increased temperatures typically improving its dissolution in organic solvents.

In summary, the solubility of diazomethane is characterized by its readiness to dissolve in various organic solvents while remaining insoluble in water. This duality makes it a valuable compound in the realm of organic chemistry, where selective solubility is often key to successful reactions.

Interesting facts

Interesting Facts about Diazomethane

Diazomethane, a simple yet fascinating compound, has garnered attention in the chemistry community for several reasons:

  • Unique Structure: Diazomethane is notable for its diazo functional group, characterized by the presence of two nitrogen atoms connected by a double bond, which imparts unique reactivity to the molecule.
  • Chemical Reactivity: This compound is a powerful and versatile reagent in organic synthesis. Its ability to generate carbenes makes it invaluable for various cycloaddition reactions and the formation of carbon-carbon bonds.
  • Historical Significance: Diazomethane has played a significant role in the development of the field of organic chemistry. Its use in the early 20th century to synthesize natural products showcased its potential and paved the way for synthetic organic chemistry as we know it today.
  • Safety Considerations: Despite its usefulness, diazomethane is known for its high reactivity and potential hazards. It is considered toxic and can form explosive compounds under certain conditions, emphasizing the need for safe handling practices in the laboratory environment.
  • Applications: Beyond its role in synthetic chemistry, diazomethane is also employed in the preparation of amides, esters, and in the detection of functional groups in organic compounds.

In the words of noted chemist R. Paul, "The use of diazomethane has opened avenues in organic synthesis that have been previously thought impossible." This reflects the compound's lasting impact on the scientific community and the continuous exploration of its properties and reactivity.

Ultimately, diazomethane serves as a reminder of the delicate balance between innovation and safety in the world of chemistry, encouraging chemists to approach their work with both curiosity and care.

Synonyms
DIAZOMETHANE
Azimethylene
334-88-3
Acomethylene
Methane, diazo-
Diazonium methylide
EINECS 206-382-7
CCRIS 205
HSDB 1628
BRN 0102415
DIAZOMETHANE [MI]
60A625P70P
DIAZOMETHANE [HSDB]
DIAZOMETHANE [IARC]
DTXSID0024008
CHEBI:73716
4-01-00-03056 (Beilstein Handbook Reference)
METHANE,DIAZO
DIAZOMETHANE (IARC)
azomethylene
diazomethan
diazo methane
diazo-methane
CNN radical
UNII-60A625P70P
CNN
DIAZOMETHYL GROUP
DIAZONIUM, METHYLIDE
Diazomethane (ACGIH:OSHA)
DTXCID604008
AKOS015901056
DB-264755
NS00029498
C19387
Q413683
186581-53-3
206-382-7