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Triethylamine

Triethylamine
Skeletal formula of triethylamine
Ball and stick model of triethylamine
Spacefill model of triethylamine
Names
Preferred IUPAC name
N,N-Diethylethanamine
Other names
(Triethyl)amine
Triethylamine (deprecated)
Identifiers
121-44-8 YesY
3D model (Jmol) Interactive image
Abbreviations TEA
605283
ChEBI CHEBI:35026 YesY
ChEMBL ChEMBL284057 YesY
ChemSpider 8158 YesY
ECHA InfoCard 100.004.064
EC Number 204-469-4
KEGG C14691 YesY
MeSH triethylamine
PubChem 8471
RTECS number YE0175000
UNII VOU728O6AY YesY
UN number 1296
Properties
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
66 μmol Pa−1 kg−1
Acidity (pKa) 10.75 (for the conjugate acid) (H2O), 9.00 (DMSO)
-81.4·10−6 cm3/mol
1.401
Thermochemistry
216.43 J K−1 mol−1
−169 kJ mol−1
−4.37763 to −4.37655 MJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H302, H312, H314, H332
P210, P280, P305+351+338, P310
Highly Flammable F Corrosive C
R-phrases R11, R20/21/22, R35
S-phrases (S1/2), S3, S16, S26, S29, S36/37/39
NFPA 704
Flammability code 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., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −15 °C (5 °F; 258 K)
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)
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
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
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 pKa 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):


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