Diethylamine

Diethylamine[1]
Names
	Preferred IUPAC name N-Ethylethanamine
	Other names (Diethyl)amine; Diethylamine (deprecated[2])
Identifiers
CAS Number	109-89-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	605268
ChEBI	CHEBI:85259 ;
ChEMBL	ChEMBL1189 ;
ChemSpider	7730 ;
ECHA InfoCard	100.003.380
EC Number	203-716-3;
MeSH	diethylamine
PubChem CID	8021;
RTECS number	HZ8750000;
UNII	B035PIS86W ;
UN number	1154
CompTox Dashboard (EPA)	DTXSID6021909 ;
	InChI InChI=1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3 Key: HPNMFZURTQLUMO-UHFFFAOYSA-N ;
	SMILES CCNCC;
Properties
Chemical formula	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
Solubility in water	Miscible
log P	0.657
Vapor pressure	24.2–97.5 kPa
Henry's law; constant (kH)	150 μmol Pa−1 kg−1
Acidity (pKa)	10.98 (of ammonium form)
Magnetic susceptibility (χ)	-56.8·10−6 cm3/mol
Refractive index (nD)	1.385
Thermochemistry
Heat capacity (C)	178.1 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−131 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−3.035 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H312, H314, H332
Precautionary statements	P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	3 3 1
Flash point	−23 °C (−9 °F; 250 K)
Autoignition; temperature	312 °C (594 °F; 585 K)
Explosive limits	1.8–10.1%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	540 mg/kg (rat, oral); 500 mg/kg (mouse, oral)[3]
LC50 (median concentration)	4000 ppm (rat, 4 hr)[3]
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 25 ppm (75 mg/m3)[4]
REL (Recommended)	TWA 10 ppm (30 mg/m3) ST 25 ppm (75 mg/m3)[4]
IDLH (Immediate danger)	200 ppm[4]
Safety data sheet (SDS)	hazard.com
Related compounds
Related amines	Ethylamine; Dimethylamine; Trimethylamine; Triethylamine; Diisopropylamine;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

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.[7]

Safety

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

References

Merck Index, 12th Edition, 3160
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.
"Diethylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
NIOSH Pocket Guide to Chemical Hazards. "#0209". National Institute for Occupational Safety and Health (NIOSH).
Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
Shulgin, Alexander. "Erowid Online Books:"TIHKAL" - #26 LSD-25". www.erowid.org. Retrieved 12 August 2019.
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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[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.

[IDLH-3] "Diethylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[PGCH-4] NIOSH Pocket Guide to Chemical Hazards. "#0209". National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-5] Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.{{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] 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.