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Triethylamine information


Not to be confused with Triethanolamine.
Triethylamine
Skeletal formula of triethylamine
Ball and stick model of triethylamine
Ball and stick model of triethylamine
Spacefill model of triethylamine
Spacefill model of triethylamine
Names
Preferred IUPAC name
N,N-Diethylethanamine
Other names
(Triethyl)amine
Triethylamine (no longer IUPAC name[1])
Identifiers
CAS Number
  • 121-44-8 checkY
3D model (JSmol)
  • Interactive image
Abbreviations TEA[2]
Beilstein Reference
 605283
ChEBI
  • CHEBI:35026 checkY
ChEMBL
  • ChEMBL284057 checkY
ChemSpider
  • 8158 checkY
ECHA InfoCard 100.004.064 Edit this at Wikidata
EC Number
  • 204-469-4
KEGG
  • C14691 checkY
MeSH triethylamine
PubChem CID
  • 8471
RTECS number
  • YE0175000
UNII
  • VOU728O6AY checkY
UN number 1296
CompTox Dashboard (EPA)
  • DTXSID3024366 Edit this at Wikidata
InChI
  • InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 checkY
    Key: ZMANZCXQSJIPKH-UHFFFAOYSA-N checkY
SMILES
  • CCN(CC)CC
Properties[5]
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[3]
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)[4]
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
 GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Signal word
 Danger
Hazard statements
 H225, H302, H312, H314, H332
Precautionary statements
 P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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)[7]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 25 ppm (100 mg/m3)[6]
REL (Recommended)
 None established[6]
IDLH (Immediate danger)
 200 ppm[6]
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).
checkY verify (what is checkY☒N ?)
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.

  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
  3. ^ "MSDS - 471283". www.sigmaaldrich.com. Retrieved 2020-06-17.
  4. ^ Cite error: The named reference David Evans Research Group was invoked but never defined (see the help page).
  5. ^ The Merck Index (11th ed.). 9582.
  6. ^ a b c 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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oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine. It is one of the many oxidation reactions commonly referred to as 'activated...

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derivative of aluminium monoiodide is the cyclic adduct formed with triethylamine, Al4I4(NEt3)4. Al2O and Al2S also exist but are very unstable. Very...

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acylations are carried out in the presence of a base such as pyridine, triethylamine, or DMAP, which act as catalysts to help promote the reaction and as...

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TCPO

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of a base such as triethylamine. This method produces crude TCPO with a by-product of triethylamine hydrochloride. The triethylamine hydrochloride can...

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another solution of CH2Cl2-containing methylamine hydrochloride and triethylamine. Hydrochloric acid (HCl) is then added and the aqueous layer is removed...

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meals, its intestinal microbes metabolize them into fishy-smelling triethylamine, which ends up in the egg. The unpredictable diet of free-range hens...

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substituted double bond) preferentially forms due to sterics. When using triethylamine, a weak base, the thermodynamic silyl enol ether (with a more substituted...

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this reaction, ethylamine is coproduced together with diethylamine and triethylamine. In aggregate, approximately 80M kilograms/year of these three amines...

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Acid dissociation constant

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(C5H5N) = 5.25 and pKaH ((CH3CH2)3N) = 10.75 indicate that (CH3CH2)3N (triethylamine) is a stronger base than C5H5N (pyridine). An amphoteric substance is...

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and ammonia. Diethylamine is obtained together with ethylamine and triethylamine. Annual production of the three ethylamines was estimated in 2000 to...

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Polyester

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alcohol may also be carried out in one phase using tertiary amines (e. g. triethylamine, Et3N) or pyridine as acid acceptors: While acyl chloride-based polyesterifications...

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from a solution of methanol and tetrahydrofuran after the addition of triethylamine, resulting in a 50% yield. Chemists report having struggled to reproduce...

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into recycling the triethylamine and methanol solvents. Progress has also been made in attempting to eliminate the need for triethylamine altogether. Technical...

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are grounded and added into toluene solvent. The solution, along with triethylamine and acetic anhydride, is refluxed at ~110°C for 9 hours; after that...

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reaction to make amines, and (in aqueous solution or in its azeotrope with triethylamine) for hydrogenation of ketones. Formic acid is unique among the carboxylic...

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