Triethylamine

Triethylamine
Ball and stick model of triethylamine	Spacefill model of triethylamine
Names
	Preferred IUPAC name N,N-Diethylethanamine
	Other names (Triethyl)amine; Triethylamine (no longer IUPAC name)
Identifiers
CAS Number	121-44-8 ;
3D model (JSmol)	Interactive image;
Abbreviations	TEA
Beilstein Reference	605283
ChEBI	CHEBI:35026 ;
ChEMBL	ChEMBL284057 ;
ChemSpider	8158 ;
ECHA InfoCard	100.004.064
EC Number	204-469-4;
KEGG	C14691 ;
MeSH	triethylamine
PubChem CID	8471;
RTECS number	YE0175000;
UNII	VOU728O6AY ;
UN number	1296
CompTox Dashboard (EPA)	DTXSID301024181 DTXSID3024366, DTXSID301024181 ;
	InChI InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 Key: ZMANZCXQSJIPKH-UHFFFAOYSA-N ;
	SMILES CCN(CC)CC;
Properties
Chemical formula	C6H15N
Molar mass	101.193 g·mol−1
Appearance	Colourless liquid
Odor	Fishy, ammoniacal
Density	0.7255 g mL−1
Melting point	−114.70 °C; −174.46 °F; 158.45 K
Boiling point	88.6 to 89.8 °C; 191.4 to 193.5 °F; 361.7 to 362.9 K
Solubility in water	112.4 g/L at 20 °C
Solubility	miscible with organic solvents
log P	1.647
Vapor pressure	6.899–8.506 kPa
Henry's law; constant (kH)	66 μmol Pa−1 kg−1
Acidity (pKa)	10.75 (for the conjugate acid) (H2O), 9.00 (DMSO)
Magnetic susceptibility (χ)	-81.4·10−6 cm3/mol
Refractive index (nD)	1.401
Thermochemistry
Heat capacity (C)	216.43 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−169 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−4.37763 to −4.37655 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 0
Flash point	−15 °C (5 °F; 258 K)
Autoignition; temperature	312 °C (594 °F; 585 K)
Explosive limits	1.2–8%
Threshold limit value (TLV)	2 ppm (8 mg/m3) (TWA), ; 4 ppm (17 mg/m3) (STEL)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	580 mg kg−1 (dermal, rabbit); 730 mg kg−1 (oral, rat);
LCLo (lowest published)	1425 ppm (mouse, 2 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 25 ppm (100 mg/m3)
REL (Recommended)	None established
IDLH (Immediate danger)	200 ppm
Related compounds
Related amines	Dimethylamine; Trimethylamine; N-Nitrosodimethylamine; Diethylamine; Diisopropylamine; Dimethylaminopropylamine; Diethylenetriamine; N,N-Diisopropylethylamine; Triisopropylamine; Tris(2-aminoethyl)amine; Mechlorethamine; HN1 (nitrogen mustard); HN3 (nitrogen mustard);
Related compounds	Unsymmetrical dimethylhydrazine; Biguanide; Dithiobiuret; Agmatine;
	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

Triethylamine is the chemical compound with the formula N(CH₂CH₃)₃, commonly abbreviated Et₃N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation.^[8]^[9] It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed in organic synthesis, usually as a base.

^ "Front Matter". 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.
^ X. Bories-Azeau, S. P. Armes, and H. J. W. van den Haak, Macromolecules 2004, 37, 2348 PDF
^ "MSDS - 471283". www.sigmaaldrich.com. Retrieved 2020-06-17.
^ Cite error: The named reference David Evans Research Group was invoked but never defined (see the help page).
^ The Merck Index (11th ed.). 9582.
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0633". National Institute for Occupational Safety and Health (NIOSH).
^ "Triethylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ "Ethanolamine Compounds (MEA, DEA, TEA And Others)". Safe Cosmetics. Retrieved 2020-06-17.
^ "tetraethylammonium | Ligand page | IUPHAR/BPS Guide to PHARMACOLOGY". www.guidetopharmacology.org. Retrieved 2020-06-17.

[1] "Front Matter". 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.

[2] X. Bories-Azeau, S. P. Armes, and H. J. W. van den Haak, Macromolecules 2004, 37, 2348 PDF

[solubility-3] "MSDS - 471283". www.sigmaaldrich.com. Retrieved 2020-06-17.

[David_Evans_Research_Group-4] Cite error: The named reference David Evans Research Group was invoked but never defined (see the help page).

[Merck-5] The Merck Index (11th ed.). 9582.

[PGCH-6] NIOSH Pocket Guide to Chemical Hazards. "#0633". National Institute for Occupational Safety and Health (NIOSH).

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

[8] "Ethanolamine Compounds (MEA, DEA, TEA And Others)". Safe Cosmetics. Retrieved 2020-06-17.

[9] "tetraethylammonium | Ligand page | IUPHAR/BPS Guide to PHARMACOLOGY". www.guidetopharmacology.org. Retrieved 2020-06-17.

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