Diethylamine

Diethylamine is an organic compound with the formula (CH₃CH₂)₂NH. It is classified as a secondary amine. It is a flammable, volatile 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.

Diethylamine^[1]

Names
Preferred IUPAC name N-Ethylethanamine
Other names (Diethyl)amine Diethylamine (deprecated[2])
Identifiers
CAS Number	109-89-7 Y
3D model (JSmol)	Interactive image
Beilstein Reference	605268
ChEBI	CHEBI:85259 Y
ChEMBL	ChEMBL1189 Y
ChemSpider	7730 Y
ECHA InfoCard	100.003.380
EC Number	203-716-3
MeSH	diethylamine
PubChem CID	8021
RTECS number	HZ8750000
UNII	B035PIS86W Y
UN number	1154
CompTox Dashboard (EPA)	DTXSID501061682 DTXSID6021909, DTXSID501061682
InChI InChI=1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3 Y Key: HPNMFZURTQLUMO-UHFFFAOYSA-N Y
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). N verify (what is YN ?) Infobox references

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 the 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]