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Dimethylamine

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Dimethylamine
Structural formula
Ball-and-stick model
Names
IUPAC name Dimethylamine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.272 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H7N/c1-3-2/h3H,1-2H3Key: ROSDSFDQCJNGOL-UHFFFAOYSA-N
  • InChI=1/C2H7N/c1-3-2/h3H,1-2H3Key: ROSDSFDQCJNGOL-UHFFFAOYAM
SMILES
  • N(C)C
Properties
Chemical formula C2H7N
Molar mass 45.08 g/mol
Appearance Colorless gas with pungent odor
Density 0.67 g/cm (21 °C, 1 atm)
Melting point −92.2 °C (−134.0 °F; 181.0 K)
Boiling point 7 °C (45 °F; 280 K)
Solubility in water 354 g/100 mL
Acidity (pKa) 10.64
Thermochemistry
Std enthalpy of
formation (ΔfH298) 		-18.422 kJ/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3 4 0
Flash point Flammable gas
Explosive limits 2.8–14.4%
Supplementary data page
]
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

Structure and properties

The molecule consists of a nitrogen atom with two methyl substituents 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:

2 CH3OH + NH3 → (CH3)2NH + 2 H2O

Uses

Dimethylamine is a precursor to several industrially significant compounds. It reacts with carbon disulfide 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 agrichemicals and pharmaceuticals, such as dimefox and diphenhydramine, respectively. The chemical weapon tabun is derived from dimethylamine. The surfactant lauryl dimethylamine oxide is found in soaps and cleaning compounds. Unsymmetrical dimethylhydrazine, a rocket fuel, is prepared from dimethylamine.

Biochemistry

The German cockroach utilizes dimethylamine as a pheromone for communication.

DMA 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 DMA by nitrogen oxides present in acid rain in highly industrialized countries.

See also

References

  1. Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
  2. ^ A. B. van Gysel, W. Musin "Methylamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. doi:10.1002/14356007.a16 535
  3. Corbin D.R.; Schwarz S.; Sonnichsen G.C. (1997). "Methylamines synthesis: A review". Catalysis Today. 37 (2): 71–102. doi:10.1016/S0920-5861(97)00003-5.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, pages 3284-3286
  5. Zhang AQ, Mitchell SC, Smith RL (1998). "Dimethylamine formation in the rat from various related amine precursors". Food Chem. Toxicol. 36 (11): 923–7. doi:10.1016/S0278-6915(98)00074-X. PMID 9771553. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

External links

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