Methanesulfonyl azide is the
azide
In chemistry, azide (, ) is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant ...
of
methanesulfonic acid
Methanesulfonic acid (MsOH, MSA) or methanesulphonic acid (in British English) is an organosulfuric, colorless liquid with the molecular formula and structure . It is the simplest of the alkylsulfonic acids (). Salts and esters of methanesul ...
. It is used as a reagent for the production of
diazo compounds
In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Overall charge-neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds ...
.
Preparation
Methanesulfonyl azide can be prepared from
methanesulfonyl chloride
Methanesulfonyl chloride (mesyl chloride) is an organosulfur compound with the formula . Using the organic pseudoelement symbol Ms for the methanesulfonyl (or mesyl) group –, it is frequently abbreviated MsCl in reaction schemes or equations. It ...
by reaction with
sodium azide
Sodium azide is an inorganic compound with the formula . This colorless salt is the gas-forming component in some car airbag systems. It is used for the preparation of other azide compounds. It is highly soluble in water and is acutely poisonou ...
in
ethanol
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
or
methanol
Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...
,
Preparation ''
in situ
is a Latin phrase meaning 'in place' or 'on site', derived from ' ('in') and ' ( ablative of ''situs'', ). The term typically refers to the examination or occurrence of a process within its original context, without relocation. The term is use ...
'' is also possible, for example in
acetonitrile
Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not class ...
, and is advantageous to avoid explosion hazards.
Properties
Methanesulfonyl azide melts at 18 °C and decomposes from 120 °C.
Like many other
azides
In chemistry, azide (, ) is a Linear molecular geometry, linear, polyatomic anion with the Chemical formula, formula and Chemical structure, structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the ...
, it is explosive.
At low temperature, methanesulfonyl azide crystallizes in the
triclinic crystal system
class=skin-invert-image, 180px, Triclinic (a ≠ b ≠ c ≠ a and α, β, γ, 90° pairwise different)
In crystallography, the triclinic (or anorthic) crystal system is one of the seven crystal systems. A crystal system is described by three b ...
in the
space group
In mathematics, physics and chemistry, a space group is the symmetry group of a repeating pattern in space, usually in three dimensions. The elements of a space group (its symmetry operations) are the rigid transformations of the pattern that ...
''P''1 with the
lattice parameter
A lattice constant or lattice parameter is one of the physical dimensions and angles that determine the geometry of the unit cells in a crystal lattice, and is proportional to the distance between atoms in the crystal. A simple cubic crystal has ...
s ''a'' = 5.6240 Å; ''b'' = 5.9498 Å, ''c'' = 7.6329 Å, ''α'' = 72.216°, ''β'' = 70.897°, and ''γ'' = 88.601°, and two molecules per
unit cell
In geometry, biology, mineralogy and solid state physics, a unit cell is a repeating unit formed by the vectors spanning the points of a lattice. Despite its suggestive name, the unit cell (unlike a unit vector
In mathematics, a unit vector i ...
.
Mesyl azide is an antidote for
hydrogen sulfide
Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is toxic, corrosive, and flammable. Trace amounts in ambient atmosphere have a characteristic foul odor of rotten eggs. Swedish chemist ...
poisoning in
mice
A mouse (: mice) is a small rodent. Characteristically, mice are known to have a pointed snout, small rounded ears, a body-length scaly tail, and a high breeding rate. The best known mouse species is the common house mouse (''Mus musculus' ...
.
Reactions
Methanesulfonyl azide is part of the
sulfonyl azide
In organosulfur chemistry, a sulfonyl group is either a functional group found primarily in sulfones, or a substituent obtained from a sulfonic acid by the removal of the hydroxyl group, similarly to acyl groups.
Group
Sulfonyl groups can be wr ...
s, a family of reagents for
diazo transfer. Within the family, methanesulfonyl azide has particularly simple, inexpensive production and a straightforward purification of the reaction mixture.
The
photolysis
Photodissociation, photolysis, photodecomposition, or photofragmentation is a chemical reaction in which molecules of a chemical compound are broken down by absorption of light or photons. It is defined as the interaction of one or more photons wi ...
of methanesulfonyl azide in a
matrix
Matrix (: matrices or matrixes) or MATRIX may refer to:
Science and mathematics
* Matrix (mathematics), a rectangular array of numbers, symbols or expressions
* Matrix (logic), part of a formula in prenex normal form
* Matrix (biology), the m ...
of
argon
Argon is a chemical element; it has symbol Ar and atomic number 18. It is in group 18 of the periodic table and is a noble gas. Argon is the third most abundant gas in Earth's atmosphere, at 0.934% (9340 ppmv). It is more than twice as abu ...
or
neon
Neon is a chemical element; it has symbol Ne and atomic number 10. It is the second noble gas in the periodic table. Neon is a colorless, odorless, inert monatomic gas under standard conditions, with approximately two-thirds the density of ...
yields a short-lived
nitrene
In chemistry, a nitrene or imene () is the nitrogen analogue of a carbene. The nitrogen atom is uncharged and valence (chemistry)#monovalent, monovalent, so it has only 6 electrons in its valence level—two covalent bonded and four non-bonded e ...
.
If methanesulfonyl azide is irradiated in the presence of a
hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
, methanesulfonyl amide is formed, as well as ''N''-substituted derivatives by reaction with the hydrocarbon.
References
{{reflist
Methyl compounds
Azido compounds
Sulfones