Triethylamine

Triethylamine

Names
Preferred IUPAC name N,N-Diethylethanamine
Other names (Triethyl)amine Triethylamine (deprecated)
Identifiers
CAS Number	121-44-8 Y
3D model (Jmol)	Interactive image
Abbreviations	TEA
Beilstein Reference	605283
ChEBI	CHEBI:35026 Y
ChEMBL	ChEMBL284057 Y
ChemSpider	8158 Y
ECHA InfoCard	100.004.064
EC Number	204-469-4
KEGG	C14691 Y
MeSH	triethylamine
PubChem	8471
RTECS number	YE0175000
UNII	VOU728O6AY Y
UN number	1296
InChI InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 Y Key: ZMANZCXQSJIPKH-UHFFFAOYSA-N Y
SMILES CCN(CC)CC
Properties
Chemical formula	C6H15N
Molar mass	101.19 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
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
Specific heat capacity (C)	216.43 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−169 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−4.37763 to −4.37655 MJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H225, H302, H312, H314, H332
GHS precautionary statements	P210, P280, P305+351+338, P310
EU classification (DSD)	F C
R-phrases	R11, R20/21/22, R35
S-phrases	(S1/2), S3, S16, S26, S29, S36/37/39
NFPA 704	3 3 0
Flash point	−15 °C (5 °F; 258 K)
Autoignition temperature	312 °C (594 °F; 585 K)
Explosive limits	1.2–8%
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)
US health exposure limits (NIOSH):
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).
Y  (what is YN ?)
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. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia and is also the smell of the hawthorn plant. Like diisopropylethylamine (Hünig’s base), triethylamine is commonly encountered in organic synthesis.

Triethylamine is prepared by the alkylation of ammonia with ethanol:

The pK_a of protonated triethylamine is 10.75, and it can be used to prepare buffer solutions for that pH. The hydrochloride salt, triethylamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and hygroscopic powder, which decomposes when heated to 261 °C.

Triethylamine is commonly employed in organic synthesis as a base, most often in the preparation of esters and amides from acyl chlorides. Such reactions lead to the production of hydrogen chloride which combines with triethylamine to form the salt triethylamine hydrochloride, commonly called triethylammonium chloride. This reaction removes the hydrogen chloride from the reaction mixture, which is required for these reactions to proceed to completion (R, R' = alkyl, aryl):