View source for Dimethylamine

{{Chembox new|
 ImageFile=Dimethylamine-2D.png|
 Section1={{Chembox General|
  IUPACName=Dimethylamine|
  Formula=C<sub>2</sub>H<sub>7</sub>N|
  MolarMass=45.08 g/mol|
  Appearance=Colorless gas with pungent odor|
  CASNo=124-40-3|
  SMILES=CNC}}|
 Section2={{Chembox Properties|
  Density=1.883 kg/m<sup>3</sup> (21 °C, 1 atm)|
  Solubility=354 g/100 ml|
   Solvent=Water|
  MeltingPt=&minus;92.2 °C|
  BoilingPt=7 °C|
  Dipole=?}}|
 Section3={{Chembox Thermochemistry|
  DeltaHf=? kJ/mol|
  Entropy=? J/K/mol}}|
 Section4={{Chembox Hazards|
  EUClass=Highly flammable ('''F+''')<br/>Harmful ('''Xn''')|
  EUIndex=612-001-00-9|
  NFPA-H=3|
  NFPA-F=4|
  NFPA-R=0|
  RPhrases={{R12}}, {{R20}}, {{R37/38}}, |
  SPhrases={{S2}}, {{S16}}, {{S26}}, {{S39}}|
  FlashPt=Flammable gas|
  Autoignition=400 °C|
  ExploLimits=2.8&ndash;14.4%|
  RTECS=IP8750000}}|
 Section5={{Chembox Supplement}}|
 Section6={{Chembox Related|
  OtherFunctn=[[Methylamine]]<br/>[[Trimethylamine]]<br/>[[Diethylamine]]|
   Function=amine}}
}}

'''Dimethylamine''' or '''N-methylmethanamine''' or '''DMA''' is an [[organic compound]] and an [[amine]]. It is a colorless, [[Liquefy|liquefied]] and flammable gas with an [[ammonia]] and fish-like odor. Dimethylamine is generally used as a solution in water at concentrations up to around 40%.

== Chemistry ==
Dimethylamine is a [[secondary amine]]. The [[molecule]] consists of a [[nitrogen]] [[atom]] with two [[methyl]] [[substituent]]s and one [[proton]]. Dimethylamine is a [[base (chemistry)|base]] and the [[pKa]] of the [[ammonium salt]] CH<sub>3</sub>-NH<sub>2</sub><sup>+</sup>-CH<sub>3</sub> is 10.73, a value intermediate between [[methylamine]] (10.64) and [[trimethylamine]] (9.79). 
Dimethylamine reacts with acids to form salts. '''Dimethylamine hydrochloride''' is 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.<ref>{{cite journal
| author = Corbin D.R.; Schwarz S.; Sonnichsen G.C.
| title = Methylamines synthesis: A review
| journal = Catalysis Today
| year = 1997
| volume = 37 
| issue = 2
| pages = 71-102
| doi = 10.1016/S0920-5861(97)00003-5 }}
</ref>

== Biochemistry ==
The [[German cockroach]] utilizes dimethylamine as a [[pheromone]] for communication.

DMA undergoes [[nitrosation]] under weak acid conditions to give [[dimethlynitrosamine]]. This animal [[carcinogen]] 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 industrilized countries (Zhang et al. 1998).

== Uses ==
Dimethylamine is used as dehairing agent in [[tanning]],  in [[dye]]s, in [[rubber]] [[accelerator (chemistry)|accelerator]]s, in [[soap]]s and cleaning compounds and as an agricultural [[fungicide]]. In industry dimethylamine is converted to [[dimethylformamide]] and the [[surfactant]] [[lauryl dimethylamine oxide]]. It is raw material in the production of many [[pharmaceutical]]s such as [[diphenhydramine]] and also that of the [[chemical weapon]] [[tabun (nerve agent)|tabun]].

== External links  ==
* [[MSDS]] http://www.airliquide.com [http://www.airliquide.com/safety/msds/en/047_AL_EN.pdf]
* [[MSDS]] http://physchem.ox.ac.uk  [http://physchem.ox.ac.uk/MSDS/DI/dimethylamine.html]
* production at http://www.methylamines.com [http://www.methylamines.com/products/products.html]
* http://www.pherobase.com [http://www.pherobase.com/database/compounds-detail-dimethylamine.html]

==See also==
*[[Methylamine]]
*[[Trimethylamine]]

==References==
{{reflist|2}}
Zhang AQ, Mithchell SC, Smith RL (1998) Dimethylamine formation in the rat from various related amine precursors. Food Chem Toxicol 36(11):923-7

== External links ==
*{{ICSC|0260|02}} (gas)
*{{ICSC|1485|14}} (aqueous solution)
*{{PGCH|0219}}
*[http://www.airliquide.com/en/business/products/gases/gasdata/index.asp?Formula=&GasID=79&UNNumber= Properties] from [[Air Liquide]]

[[Category:Amines]]
[[Category:Pheromones]]
[[Category:Insect ecology]]

[[de:Dimethylamin]]
[[es:Dimetilamina]]
[[fr:Diméthylamine]]
[[it:Dimetilammina]]
[[nl:Dimethylamine]]
[[pl:Dimetyloamina]]
[[fi:Dimetyyliamiini]]