Dimethylamine

Dimethylamine
Dimethylamine
Identifiers
CAS number 124-40-3 YesY
PubChem 674
ChemSpider 654 YesY
UNII ARQ8157E0Q YesY
EC number 204-697-4
UN number 1032
KEGG C00543 YesY
MeSH dimethylamine
ChEBI CHEBI:17170 YesY
ChEMBL CHEMBL120433 YesY
RTECS number IP8750000
Beilstein Reference 605257
Gmelin Reference 849
3DMet B00125
Jmol-3D images Image 1
Properties[3][4]
Molecular formula C2H7N
Molar mass 45.0837 g mol−1
Exact mass 45.057849229 g mol−1
Appearance Colorless gas
Odor Ammonical, pungent
Density 680 mg cm−3 (at 20 °C)
Melting point

-92 °C, 181 K, -134 °F

Boiling point

7-9 °C, 280-282 K, 44-48 °F

Solubility in water 3.540 kg dm−3
log P −0.362
Vapor pressure 170.3 pKa (at 20 °C)
Acidity (pKa) 10.64[2]
Basicity (pKb) 3.36
Thermochemistry
Std enthalpy of
formation
ΔfHo298
−18.422 kJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H220, H302, H315, H318, H332, H335
GHS precautionary statements P210, P261, P280, P305+351+338, P410+403
EU Index 612-001-00-9
EU classification Flammable F+ Harmful Xn
R-phrases R12, R20, R37/38, R41
S-phrases (S2), S16, S26, S39
NFPA 704
NFPA 704.svg
4
3
0
Flash point −6 °C
Autoignition
temperature
401 °C
Explosive limits 2.8–14.4%
Related compounds
Related amines Diethylamine

Methylamine
Trimethylamine

 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[5]

Contents

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:[6]

2 CH3OH + NH3 → (CH3)2NH + 2 H2O

Uses

Dimethylamine is a precursor to several industrially significant compounds.[5][7] 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.[8]

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.[citation needed]

See also

References

  1. ^ "dimethylamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=674. Retrieved 21 October 2011. 
  2. ^ Hall, H.K. (1957). J. Am. Chem. Soc. 79: 5441. 
  3. ^ "Dimethylamine". NIST Chemistry WebBook. USA: National Institute of Standards and Technology. http://webbook.nist.gov/cgi/cbook.cgi?ID=C124403&Mask=1#Thermo-Gas. Retrieved 21 October 2011. 
  4. ^ "Dimethylamine 38931 - ≥99.0%". Aldrich. Sigma-Aldrich Co. http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=38931%7CALDRICH&N5=SEARCH_CONCAT_PNO. Retrieved 21 October 2011. 
  5. ^ a b 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
  6. ^ 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. 
  7. ^ Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, pages 3284-3286
  8. ^ Zhang AQ, Mitchell SC, Smith RL (November 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. 

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