Dimethylamine
Encyclopedia
Dimethylamine is an organic compound
with the formula (CH3)2NH. This secondary amine is a colorless, flammable liquified gas with an ammonia
-like odor. Dimethylamine is generally encountered as a solution in water at concentrations up to around 40%. In 2005, an estimated 270,000 tons were produced.
atom
with two methyl substituent
s and one proton
. Dimethylamine is a base
and the pKa
of the ammonium salt CH3-NH2+-CH3 is 10.73, a value above methylamine
(10.64) and trimethylamine
(9.79).
Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by catalytic reaction of methanol
and ammonia
at elevated temperatures and high pressure:
to give dimethyldithiocarbamate
, a precursor to a family of chemicals widely used in the vulcanization
of rubber
. The solvents dimethylformamide
and dimethylacetamide
are derived from dimethylamine. It is raw material for the production of many agrichemical
s and pharmaceuticals, such as dimefox
and diphenhydramine
, respectively. The chemical weapon tabun
is derived from dimethylamine. The surfactant
lauryl dimethylamine oxide is found in soap
s and cleaning compounds. Unsymmetrical dimethylhydrazine, a rocket fuel, is prepared from dimethylamine.
utilizes dimethylamine as a pheromone
for communication.
Dimethylamine undergoes nitrosation
under weak acid conditions to give dimethylnitrosamine. This animal carcinogen
has been detected and quantified in human urine samples and it may also arise from nitrosation of dimethylamine by nitrogen oxides present in acid rain in highly industrialized countries.
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...
with the formula (CH3)2NH. This secondary amine is a colorless, flammable liquified gas with an ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
-like odor. Dimethylamine is generally encountered as a solution in water at concentrations up to around 40%. In 2005, an estimated 270,000 tons were produced.
Structure and properties
The molecule consists of a nitrogenNitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
atom
Atom
The atom is a basic unit of matter that consists of a dense central nucleus surrounded by a cloud of negatively charged electrons. The atomic nucleus contains a mix of positively charged protons and electrically neutral neutrons...
with two methyl substituent
Substituent
In organic chemistry and biochemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon...
s and one proton
Proton
The proton is a subatomic particle with the symbol or and a positive electric charge of 1 elementary charge. One or more protons are present in the nucleus of each atom, along with neutrons. The number of protons in each atom is its atomic number....
. Dimethylamine is a base
Base (chemistry)
For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...
and the pKa
PKA
PKA, pKa, or other similar variations may stand for:* pKa, the symbol for the acid dissociation constant at logarithmic scale* Protein kinase A, a class of cAMP-dependent enzymes* Pi Kappa Alpha, the North-American social fraternity...
of the ammonium salt CH3-NH2+-CH3 is 10.73, a value above methylamine
Methylamine
Methylamine is the organic compound with a formula of CH3NH2. This colourless gas is a derivative of ammonia, but with one H atom replaced by a methyl group. It is the simplest primary amine. It is sold as a solution in methanol, ethanol, THF, and water, or as the anhydrous gas in pressurized...
(10.64) and trimethylamine
Trimethylamine
Trimethylamine is an organic compound with the formula N3. This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations...
(9.79).
Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by catalytic reaction of methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
and ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
at elevated temperatures and high pressure:
- 2 CH3OH + NH3 → (CH3)2NH + 2 H2O
Uses
Dimethylamine is a precursor to several industrially significant compounds. It reacts with carbon disulfideCarbon disulfide
Carbon disulfide is a colorless volatile liquid with the formula CS2. The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non-polar solvent...
to give dimethyldithiocarbamate
Dithiocarbamate
A dithiocarbamate is a functional group in organic chemistry. It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms. Sodium diethyldithiocarbamate is a common ligand in inorganic chemistry....
, a precursor to a family of chemicals widely used in the vulcanization
Vulcanization
Vulcanization or vulcanisation is a chemical process for converting rubber or related polymers into more durable materials via the addition of sulfur or other equivalent "curatives." These additives modify the polymer by forming crosslinks between individual polymer chains. Vulcanized material is...
of rubber
Rubber
Natural rubber, also called India rubber or caoutchouc, is an elastomer that was originally derived from latex, a milky colloid produced by some plants. The plants would be ‘tapped’, that is, an incision made into the bark of the tree and the sticky, milk colored latex sap collected and refined...
. The solvents dimethylformamide
Dimethylformamide
Dimethylformamide is an organic compound with the formula 2NCH. Commonly abbreviated as DMF , this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions...
and dimethylacetamide
Dimethylacetamide
Dimethylacetamide is the organic compound with the formula CH3CN2. This colorless, water miscible, high boiling liquid is commonly used as a polar solvent in organic chemistry. DMAc is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.The chemical reactions...
are derived from dimethylamine. It is raw material for the production of many agrichemical
Agrichemical
Agrochemical , a contraction of agricultural chemical, is a generic term for the various chemical products used in agriculture. In most cases, agrichemical refers to the broad range of pesticides, including insecticides, herbicides, and fungicides...
s and pharmaceuticals, such as dimefox
Dimefox
Dimefox is an organophosphorus agent and a colourless liquid with a fishy odour. The structure consists of a central phosphate atom, which is connected to an oxygen by a double bond. The phosphor also binds to a fluor atom and two aminodimethyl groups...
and diphenhydramine
Diphenhydramine
Diphenhydramine hydrochloride is a first-generation antihistamine possessing anticholinergic, antitussive, antiemetic, and sedative properties which is mainly used to treat allergies. Like most other first-generation antihistamines, the drug also has a powerful hypnotic effect, and for this reason...
, respectively. The chemical weapon tabun
Tabun (nerve agent)
Tabun or GA is an extremely toxic chemical substance. It is a clear, colorless, and tasteless liquid with a faint fruity odor. It is classified as a nerve agent because it fatally interferes with normal functioning of the mammalian nervous system...
is derived from dimethylamine. The surfactant
Surfactant
Surfactants are compounds that lower the surface tension of a liquid, the interfacial tension between two liquids, or that between a liquid and a solid...
lauryl dimethylamine oxide is found in soap
Soap
In chemistry, soap is a salt of a fatty acid.IUPAC. "" Compendium of Chemical Terminology, 2nd ed. . Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford . XML on-line corrected version: created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN...
s and cleaning compounds. Unsymmetrical dimethylhydrazine, a rocket fuel, is prepared from dimethylamine.
Biochemistry
The German cockroachGerman cockroach
The German cockroach is a small species of cockroach, measuring about to long; however, they are known to get bigger. It can be tan through brown to almost black, and has two dark parallel streaks running from the head to the base of the wings. Although it has wings, it is unable to sustain flight...
utilizes dimethylamine as a pheromone
Pheromone
A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...
for communication.
Dimethylamine undergoes nitrosation
Nitrosation
Nitrosation is a process of converting organic compounds into nitroso derivatives, i.e. compounds containing the R-NO functionality.-C-Nitroso compounds:C-Nitroso compounds, such as nitrosobenzene, are typically prepared by oxidation of hydroxylamines:...
under weak acid conditions to give dimethylnitrosamine. This animal carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...
has been detected and quantified in human urine samples and it may also arise from nitrosation of dimethylamine by nitrogen oxides present in acid rain in highly industrialized countries.
External links
(gas) (aqueous solution)- Properties from Air LiquideAir LiquideL'Air Liquide S.A., or Air Liquide , is a major French company supplying industrial gases and services to various industries including medical, chemical and electronic manufacturers. Founded in 1902, it is first in the world market in its field, now operating in over 80 countries. It is...
- MSDS at airliquide.com
- MSDS at physchem.ox.ac.uk