Diethylamine[1]
Skeletal formula of diethylamine
Ball and stick model of the diethylamine molecule
Names
Preferred IUPAC name
N-Ethylethanamine
Other names
(Diethyl)amine
Diethylamine (deprecated[2])
Identifiers
3D model (JSmol)
605268
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.380 Edit this at Wikidata
EC Number
  • 203-716-3
MeSH diethylamine
RTECS number
  • HZ8750000
UNII
UN number 1154
  • InChI=1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3 checkY
    Key: HPNMFZURTQLUMO-UHFFFAOYSA-N checkY
  • CCNCC
Properties
C4H11N
Molar mass 73.139 g·mol−1
Appearance Colourless liquid
Odor fishy, ammonical
Density 0.7074 g mL−1
Melting point −49.80 °C; −57.64 °F; 223.35 K
Boiling point 54.8 to 56.4 °C; 130.5 to 133.4 °F; 327.9 to 329.5 K
Miscible
log P 0.657
Vapor pressure 24.2–97.5 kPa
150 μmol Pa−1 kg−1
Acidity (pKa) 10.98 (of ammonium form)
-56.8·10−6 cm3/mol
1.385
Thermochemistry
178.1 J K−1 mol−1
−131 kJ mol−1
−3.035 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Danger
H225, H302, H312, H314, H332
P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
3
1
Flash point −23 °C (−9 °F; 250 K)
312 °C (594 °F; 585 K)
Explosive limits 1.8–10.1%
Lethal dose or concentration (LD, LC):
540 mg/kg (rat, oral)
500 mg/kg (mouse, oral)[4]
4000 ppm (rat, 4 hr)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 25 ppm (75 mg/m3)[3]
REL (Recommended)
 TWA 10 ppm (30 mg/m3) ST 25 ppm (75 mg/m3)[3]
IDLH (Immediate danger)
 200 ppm[3]
Safety data sheet (SDS) hazard.com
Related compounds
Related amines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.

Production and uses

The alumina-catalyzed reaction makes diethylamine from ethanol and ammonia. Diethylamine is obtained together with ethylamine and triethylamine. Annual production of the three ethylamines was estimated in 2000 to be 80,000,000 kg.[5]

Diethylamine is used in the production of corrosion inhibitor N,N-diethylaminoethanol, by reaction with ethylene oxide. It is also a precursor to a wide variety of other commercial products. It is also sometimes used in the illicit production of LSD.[6]

Organic chemistry

As the most abundantly available secondary amine that is liquid at room temperature, diethylamine has been extensively deployed in chemical synthesis. Its reactions illustrate the pattern seen for many other dialkylamines. It participates in Mannich reactions involving the installation of diethylaminomethyl substituents.[7][8][9] Alkylation gives the tertiary amine.[10] With trimethylsilyl chloride, it reacts to give the silylamide.[11]

Supramolecular structure

Supramolecular helix of diethylamine

Diethylamine is the smallest and simplest molecule that features a supramolecular helix as its lowest energy aggregate. Other similarly sized hydrogen-bonding molecules favor cyclic structures.[12]

Safety

Diethylamine has low toxicity, but the vapor causes transient impairment of vision.[5]

References

  1. ^ Merck Index, 12th Edition, 3160
  2. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 671. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0209". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ a b "Diethylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ a b Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3527306732.((cite encyclopedia)): CS1 maint: multiple names: authors list (link)
  6. ^ Shulgin, Alexander. "Erowid Online Books:"TIHKAL" - #26 LSD-25". www.erowid.org. Retrieved 12 August 2019.
  7. ^ Charles E. Maxwell (1943). "β-Diethylaminomethylacetophenone Hydrochloride". Organic Syntheses. 23: 30. doi:10.15227/orgsyn.023.0030.
  8. ^ C. F. H. Allen and J. A. VanAllan (1947). "Diethylaminoacetonitrile". Organic Syntheses. 27: 20. doi:10.15227/orgsyn.027.0020.
  9. ^ Alfred L. Wilds, Robert M. Nowak, Kirtland E. McCaleb (1957). "1-Diethylamino-3-Butanone". Organic Syntheses. 37: 18. doi:10.15227/orgsyn.037.0018.((cite journal)): CS1 maint: multiple names: authors list (link)
  10. ^ W. W. Hartman (1934). "β-Diethylaminoethyl Alcohol". Organic Syntheses. 14: 28. doi:10.15227/orgsyn.014.0028.
  11. ^ W. J. Middleton, E. M. Bingham (1977). "Diethylaminosulfur Trifluoride". Organic Syntheses. 57: 50. doi:10.15227/orgsyn.057.0050.
  12. ^ Felix Hanke; Chloe J. Pugh; Ellis F. Kay; Joshua B. Taylor; Stephen M. Todd; Craig M. Robertson; Benjamin J. Slater; Alexander Steiner (2018). "The simplest supramolecular helix". Chemical Communications. 54 (47): 6012–6015. doi:10.1039/C8CC03295E. PMID 29796532.

External links

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