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Dimethylamine
 
 
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Dimethylamine is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula (CH3)2NH. This secondary amine is a colorless, flammable liquid with an ammonia
Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
- or fish-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.

molecule
Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
 consists of a nitrogen
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
 atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
 with two methyl substituent
Substituent

In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. The suffix -yl is used when naming organic compounds that contain a substituent....
s and one proton
Proton

The proton is a subatomic particle with an electric charge of +1 elementary charge. It is found in the nucleus of each atom but is also stable by itself and has a second identity as the hydrogen ion, H+....
.






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Dimethylamine is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula (CH3)2NH. This secondary amine is a colorless, flammable liquid with an ammonia
Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
- or fish-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
Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
 consists of a nitrogen
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
 atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
 with two methyl substituent
Substituent

In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. The suffix -yl is used when naming organic compounds that contain a substituent....
s and one proton
Proton

The proton is a subatomic particle with an electric charge of +1 elementary charge. It is found in the nucleus of each atom but is also stable by itself and has a second identity as the hydrogen ion, H+....
. Dimethylamine is a base
Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
 and the pKa
PKA

PKA or pKa may be:* Protein kinase A, a cAMP activated protein kinase* pKa, the symbol for Acid dissociation constant...
 of the ammonium salt CH3-NH2+-CH3 is 10.73, a value above methylamine
Methylamine

Methylamine is the organic compound with a chemical formula of CH3NH2. This colourless gas is a derivative of ammonia, wherein one H atom is replaced by a methyl group....
 (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, carbinol, wood alcohol, wood naphtha or wood spirits, is a chemical compound with chemical formula carbonhydrogen3oxygenhydrogen ....
 and ammonia
Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
 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 disulfide
Carbon disulfide

Carbon disulfide is a colorless, volatile liquid with the chemical 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, a precursor to a family of chemicals widely used in the vulcanization
Vulcanization

Vulcanization refers to a specific curing process of rubber involving high heat and the addition of sulfur or other equivalent curatives. It is a chemical process in which polymer molecules are linked to other polymer molecules by atomic bridges composed of sulfur atoms or carbon to carbon bonds....
 of rubber
Rubber

Natural rubber is an elastomer?an Elasticity_ hydrocarbon polymer?that was originally derived from a milky colloidal suspension, or latex , found in the sap of some plants....
. The solvents dimethylformamide
Dimethylformamide

Dimethylformamide is the organic compound with the chemical formula 2NCH. Commonly abbreviated DMF, this colourless liquid is miscible with Water and the majority of organic liquids....
 and dimethylacetamide
Dimethylacetamide

Dimethylacetamide is the organic compound with the chemical formula CH3CN2. This colorless, water miscible, high boiling liquid is commonly used as a polar solvent in organic chemistry....
 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 and diphenhydramine
Diphenhydramine

Diphenhydramine hydrochloride , trade name Benadryl as produced by McNeil Laboratories a division of J&J, or Dimedrol outside the U.S....
, 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 wetting agents that lower the surface tension of a liquid, allowing easier spreading, and lower the interfacial tension between two liquids....
 lauryl dimethylamine oxide is found in soap
SOAP

SOAP, originally defined as Simple Object Access Protocol, is a protocol specification for exchanging structured information in the implementation of Web Services in computer networks....
s and cleaning compounds. Unsymmetrical dimethylhydrazine, a rocket fuel, is prepared from dimethylamine.

Biochemistry

The German cockroach
German cockroach

The German cockroach or Croton bug is a small species of cockroach, measuring about to long. 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....
 utilizes dimethylamine as a pheromone
Pheromone

A pheromone is a chemical that triggers a natural behavioral response in another member of the opposite gender of the same species. There are alarm signal pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology....
 for communication.

DMA undergoes nitrosation
Nitrosation

Nitrosation is a process of converting organic compounds into nitroso derivatives, i.e. compounds containing the R-NO functionality....
 under weak acid conditions to give dimethlynitrosamine. This animal carcinogen
Carcinogen

The term carcinogen refers to any substance, radionuclide or radiation that is an agent directly involved in the promotion of cancer or in the increase of its propagation....
 has been detected and quantified in human urine samples and it may also arise from nitrosation of DMA by nitrogen oxides present in acid rain in highly industrialized countries.

See also

  • Methylamine
    Methylamine

    Methylamine is the organic compound with a chemical formula of CH3NH2. This colourless gas is a derivative of ammonia, wherein one H atom is replaced by a methyl group....
  • 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....


External links

  • (gas)
  • (aqueous solution)* from Air Liquide
    Air Liquide

    L'Air Liquide S.A., or Air Liquide , is a major France company supplying industrial gases and services to various industries including medical, chemical and electronic manufacturers....
  • MSDS at
  • MSDS at