Dimethylamine is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula (CH₃)₂NH. This secondary amine is a colorless, flammable gas with an

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogeno ...

-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

Structure and synthesis

The molecule consists of a

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seve ...

atom Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas ...

with two methyl

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and '' functional group'', as well as '' ...

s and one proton. Dimethylamine is a weak base and the

pKa PKA may refer to: * Professionally known as: ** Pen name ** Stage persona * p''K''a, 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 so ...

of the

ammonium The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternar ...

CH₃--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 Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycl ...

reaction of methanol and

at elevated temperatures and high pressure: :2 CH₃OH + NH₃ → (CH₃)₂NH + 2 H₂O

Natural occurrence

Dimethylamine is found quite widely distributed in animals and plants, and is present in many foods at the level of a few mg/kg.

Uses

Dimethylamine is a precursor to several industrially significant compounds. It reacts with

carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical ...

to give dimethyl dithiocarbamate, a precursor to zinc bis(dimethyldithiocarbamate) and other chemicals used in the sulfur vulcanization of

rubber Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Thailand, Malaysia, a ...

. The solvents dimethylformamide and dimethylacetamide are derived from dimethylamine. It is raw material for the production of many

agrichemical An agrochemical or agrichemical, a contraction of ''agricultural chemical'', is a chemical product used in industrial agriculture. Agrichemical refers to biocides (pesticides including insecticides, herbicides, fungicides and nematicides) and syn ...

s and

pharmaceutical A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the medical field and ...

s, such as dimefox and

diphenhydramine Diphenhydramine (DPH) is an antihistamine and sedative mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremor in parkinsonism, and nausea. It is taken by mouth, injected into a v ...

, respectively. The

chemical weapon A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as ...

tabun is derived from dimethylamine. The

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, fo ...

lauryl dimethylamine oxide Lauryldimethylamine oxide (LDAO), also known as dodecyldimethylamine oxide (DDAO), is an amine oxide based zwitterionic surfactant, with a C12 (dodecyl) alkyl tail. It is one of the most frequently-used surfactants of this type. Like other amine ...

is found in

soap Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are used ...

s and cleaning compounds.

Unsymmetrical dimethylhydrazine Unsymmetrical dimethylhydrazine (UDMH; 1,1-dimethylhydrazine, НДМГ or codenamed Geptil) is a chemical compound with the formula H2NN(CH3)2 that is used as a rocket propellant. It is a colorless liquid, with a sharp, fishy, ammonia-like smell ...

, a rocket fuel, is prepared from dimethylamine. :(CH₃)₂NH + NH₂Cl → (CH₃)₂NNH₂ ⋅ HCl

Reactions

It is basic, in both the Lewis and Brønsted senses. It easily forms dimethylammonium salts upon treatment with acids. Deprotonation of dimethylamine can be effected with

organolithium compound In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...

s. The resulting LiNMe₂, which adopts a cluster-like structure, serves as a source of "Me₂N⁻". This lithium amide has been used to prepare volatile metal complexes such as

tetrakis(dimethylamido)titanium Tetrakis(dimethylamino)titanium (TDMAT) is a chemical compound. The compound is generally classified as a metalorganic species, meaning that its properties are strongly influenced by the organic ligands but the compound lacks metal-carbon bonds. It ...

and

pentakis(dimethylamido)tantalum Pentakis(dimethylamido)tantalum is an organometallic compound of tantalum. It is a colorless solid that is soluble in organic solvents. It hydrolyzes readily to release dimethylamine. Synthesis and structure Ta(NMe2)5 is prepared by treating TaC ...

. It is also a Lewis base. It reacts with many carbonyl compounds. Aldehydes give aminals. For example reaction of dimethylamine and

formaldehyde Formaldehyde ( , ) ( systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section ...

gives bis(dimethylamino)methane: : 2 (CH₃)₂NH + CH₂O → CH₃)₂Nsub>2CH₂ + H₂O It converts esters to dimethylamides. Dimethylamine undergoes nitrosation to give dimethylnitrosamine, a carcinogen.

Occurrence

It is an attractant for boll weevils.''The Merck Index, 10th Ed.'' (1983), p.470, Rahway: Merck & Co.

Safety

Dimethylamine is not very toxic with the following LD₅₀ values: 736 mg/kg (mouse, i.p.); 316 mg/kg (mouse, p.o.); 698 mg/kg (rat, p.o.); 3900 mg/kg (rat, dermal); 240 mg/kg (guinea pig or rabbit, p.o.).Chemical Information Profile for Dimethylamine Borane, National Toxicology Program, NIEHS, NIH (2008), p.4: http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/DimethylamineBorane508.pdf

References

External links

* (gas) * (aqueous solution) *
Properties
from

Air Liquide Air Liquide S.A. (; ; literally " liquid air"), is a French multinational company which supplies industrial gases and services to various industries including medical, chemical and electronic manufacturers. Founded in 1902, after Linde it is ...

* MSDS a
airliquide.com
{{Authority control Alkylamines Insect pheromones Insect ecology Secondary amines