Toluidine
Encyclopedia
There are three isomers of toluidine, which are organic compound
s. These isomers are o-toluidine, m-toluidine, and p-toluidine. The o- stands for ortho- , m- stands for meta- , and p- stands for para- . All three are aryl
amine
s whose chemical structure
s are similar to aniline
except that a methyl group
is substituted onto the benzene ring. The difference between these three isomers is the position where the methyl group (-CH3) is bonded to the ring relative to the amino functional group
(-NH2); see illustration of the chemical structures below.
The chemical properties of the toluidines are quite similar to those of aniline
and toluidines have properties in common with other aromatic amines. Due to the amino group bonded to the aromatic ring, the toluidines are weakly basic
. None of the toluidines is very soluble in pure water, but will become soluble if the aqueous solution
is acidic due to formation of ammonium
salts, as usual for organic amines. At room temperature
and pressure
, ortho- and meta-toluidines are viscous liquid
s, but para-toluidine is a flaky solid
. This can be explained by the fact that the p-toluidine molecule
s are more symmetrical and fit into a crystal
line structure more easily. p-Toluidine can be obtained from reduction
of p-nitrotoluene. p-Toluidine reacts with formaldehyde
to form Tröger's base
.
Toluidines are used in the production of dye
s. They are a component of accelerators for cyanoacrylate
glues. They are toxic and are suspected human carcinogens.
The related compound o-tolidine
, used as a presumptive test for blood in forensic science, is two o-toluidine molecules linked together.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
s. These isomers are o-toluidine, m-toluidine, and p-toluidine. The o- stands for ortho- , m- stands for meta- , and p- stands for para- . All three are aryl
Aryl
In the context of organic molecules, aryl refers to any functional group or substituent derived from an aromatic ring, be it phenyl, naphthyl, thienyl, indolyl, etc....
amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
s whose chemical structure
Chemical structure
A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...
s are similar to aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
except that a methyl group
Methyl group
Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...
is substituted onto the benzene ring. The difference between these three isomers is the position where the methyl group (-CH3) is bonded to the ring relative to the amino functional group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
(-NH2); see illustration of the chemical structures below.
| Toluidine isomers | |||
|---|---|---|---|
| Common name | o-toluidine | m-toluidine | p-toluidine |
| Other names | o-methylaniline 2-methylaniline |
m-methylaniline 3-methylaniline |
p-methylaniline 4-methylaniline |
| Chemical name IUPAC nomenclature A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry .... |
2-amino-1-methylbenzene | 3-amino-1-methylbenzene | 4-amino-1-methylbenzene |
| Chemical formula Chemical formula A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound.... |
C7H9N | ||
| Molecular mass Molecular mass The molecular mass of a substance is the mass of one molecule of that substance, in unified atomic mass unit u... |
107.17 g/mol | ||
| Glass transition temperature | 189 K | 187 K | [no glass former] |
| Melting point Melting point The melting point of a solid is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depends on pressure and is usually specified at standard atmospheric pressure... |
−23 °C | −30 °C | 43 °C |
| Boiling point Boiling point The boiling point of an element or a substance is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.... |
199–200 °C | 203–204 °C | 200 °C |
| Density Density The mass density or density of a material is defined as its mass per unit volume. The symbol most often used for density is ρ . In some cases , density is also defined as its weight per unit volume; although, this quantity is more properly called specific weight... |
1.00 g/cm3 | 0.98 g/cm3 | 1.05 g/cm3 |
| CAS number CAS registry number CAS Registry Numbersare unique numerical identifiers assigned by the "Chemical Abstracts Service" toevery chemical described in the... |
[95-53-4] | [108-44-1] | [106-49-0] |
| SMILES Simplified molecular input line entry specification The simplified molecular-input line-entry specification or SMILES is a specification in form of a line notation for describing the structure of chemical molecules using short ASCII strings... |
CC1=C(N)C=CC=C1 | NC1=CC(C)=CC=C1 | NC1=CC=C(C)C=C1 |
| Disclaimer and references | |||
The chemical properties of the toluidines are quite similar to those of aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
and toluidines have properties in common with other aromatic amines. Due to the amino group bonded to the aromatic ring, the toluidines are weakly basic
Weak base
In chemistry, a weak base is a chemical base that does not ionize fully in an aqueous solution. As Brønsted–Lowry bases are proton acceptors, a weak base may also be defined as a chemical base in which protonation is incomplete. This results in a relatively low pH compared to strong bases...
. None of the toluidines is very soluble in pure water, but will become soluble if the aqueous solution
Aqueous solution
An aqueous solution is a solution in which the solvent is water. It is usually shown in chemical equations by appending aq to the relevant formula, such as NaCl. The word aqueous means pertaining to, related to, similar to, or dissolved in water...
is acidic due to formation of ammonium
Ammonium
The ammonium cation is a positively charged polyatomic cation with the chemical formula NH. It is formed by the protonation of ammonia...
salts, as usual for organic amines. At room temperature
Temperature
Temperature is a physical property of matter that quantitatively expresses the common notions of hot and cold. Objects of low temperature are cold, while various degrees of higher temperatures are referred to as warm or hot...
and pressure
Pressure
Pressure is the force per unit area applied in a direction perpendicular to the surface of an object. Gauge pressure is the pressure relative to the local atmospheric or ambient pressure.- Definition :...
, ortho- and meta-toluidines are viscous liquid
Liquid
Liquid is one of the three classical states of matter . Like a gas, a liquid is able to flow and take the shape of a container. Some liquids resist compression, while others can be compressed. Unlike a gas, a liquid does not disperse to fill every space of a container, and maintains a fairly...
s, but para-toluidine is a flaky solid
Solid
Solid is one of the three classical states of matter . It is characterized by structural rigidity and resistance to changes of shape or volume. Unlike a liquid, a solid object does not flow to take on the shape of its container, nor does it expand to fill the entire volume available to it like a...
. This can be explained by the fact that the p-toluidine molecule
Molecule
A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...
s are more symmetrical and fit into a crystal
Crystal
A crystal or crystalline solid is a solid material whose constituent atoms, molecules, or ions are arranged in an orderly repeating pattern extending in all three spatial dimensions. The scientific study of crystals and crystal formation is known as crystallography...
line structure more easily. p-Toluidine can be obtained from reduction
Redox
Redox reactions describe all chemical reactions in which atoms have their oxidation state changed....
of p-nitrotoluene. p-Toluidine reacts with formaldehyde
Formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...
to form Tröger's base
Tröger's base
Tröger's base is an organic compound that exhibits chirality due to the presence of two bridgehead stereogenic nitrogen atoms in its structure. The compound was first synthesised in 1887 from p-toluidine and formaldehyde in acid solution by Julius Tröger. It took until 1935 for the elucidation of...
.
Toluidines are used in the production of dye
Dye
A dye is a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and requires a mordant to improve the fastness of the dye on the fiber....
s. They are a component of accelerators for cyanoacrylate
Cyanoacrylate
Cyanoacrylate is the generic name for cyanoacrylate based fast-acting adhesives such as methyl 2-cyanoacrylate, ethyl-2-cyanoacrylate , and n-butyl cyanoacrylate...
glues. They are toxic and are suspected human carcinogens.
The related compound o-tolidine
Tolidine
Tolidine is a group of isomeric organic compounds, the most prevalent of which is 2-tolidine .-Chemistry:2-Tolidine is slightly soluble in water and has a melting point of 129 °C. It readily forms salts with acids, such as the hydrochloride which is commercially available...
, used as a presumptive test for blood in forensic science, is two o-toluidine molecules linked together.