Trimethylamine

Trimethylamine^[1]
Ball and stick model of trimethylamine	Spacefill model of trimethylamine
Names
	Preferred IUPAC name N,N-Dimethylmethanamine
	Other names (Trimethyl)amine (The name trimethylamine is deprecated.)
Identifiers
CAS Number	75-50-3 ;
3D model (JSmol)	Interactive image;
3DMet	B00133;
Beilstein Reference	956566
ChEBI	CHEBI:18139 ;
ChEMBL	ChEMBL439723 ;
ChemSpider	1114 ;
ECHA InfoCard	100.000.796
EC Number	200-875-0;
KEGG	C00565 ;
PubChem CID	1146;
RTECS number	PA0350000;
UNII	LHH7G8O305 ;
UN number	1083
CompTox Dashboard (EPA)	DTXSID2026238 ;
	InChI InChI=1S/C3H9N/c1-4(2)3/h1-3H3 Key: GETQZCLCWQTVFV-UHFFFAOYSA-N ;
	SMILES CN(C)C;
Properties
Chemical formula	C3H9N
Molar mass	59.112 g·mol−1
Appearance	Colorless gas
Odor	Fishy, ammoniacal
Density	670 kg m−3 (at 0 °C); 627.0 kg m−3 (at 25 °C)
Melting point	−117.20 °C; −178.96 °F; 155.95 K
Boiling point	3 to 7 °C; 37 to 44 °F; 276 to 280 K
Solubility in water	Miscible
log P	0.119
Vapor pressure	188.7 kPa (at 20 °C)
Henry's law; constant (kH)	95 μmol Pa−1 kg−1
Basicity (pKb)	4.19
Dipole moment	0.612 D
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−24.5 to −23.0 kJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220, H315, H318, H332, H335
Precautionary statements	P210, P261, P280, P305+P351+P338
NFPA 704 (fire diamond)	2 4 0
Flash point	−7 °C (19 °F; 266 K)
Autoignition; temperature	190 °C (374 °F; 463 K)
Explosive limits	2–11.6%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	500 mg kg−1 (oral, rat)
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 10 ppm (24 mg/m3) ST 15 ppm (36 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related amines	Dimethylamine; N-Nitrosodimethylamine; Diethylamine; Triethylamine; Diisopropylamine; Dimethylaminopropylamine; Diethylenetriamine; N,N-Diisopropylethylamine; Triisopropylamine; Tris(2-aminoethyl)amine; Mechlorethamine; HN1 (nitrogen mustard); HN3 (nitrogen mustard);
Related compounds	Unsymmetrical dimethylhydrazine; Biguanide; Dithiobiuret;
	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

Trimethylamine (TMA) is an organic compound with the formula N(CH₃)₃. It is a trimethylated derivative of ammonia. TMA is widely used in industry.^[5]^[6] At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes on contact.^[7] At lower concentrations, it has a "fishy" odor, the odor associated with rotting fish.

^ Merck Index, 11th Edition, 9625.
^ IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-62.2.2.1". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
^ Swift, Elijah; Hochanadel, Helen Phillips (May 1945). "The Vapor Pressure of Trimethylamine from 0 to 40°". Journal of the American Chemical Society. 67 (5): 880–881. doi:10.1021/ja01221a508.
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0636". National Institute for Occupational Safety and Health (NIOSH).
^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).
^ Ashford, Robert D. (2011). Ashford's Dictionary of Industrial Chemicals (3rd ed.). Wavelength. p. 9362. ISBN 978-0-9522674-3-0.
^ "Trimethylamine [MAK Value Documentation, 1983]", The MAK-Collection for Occupational Health and Safety, Wiley-VCH Verlag GmbH & Co. KGaA, 27 October 2014, pp. 1–9, doi:10.1002/3527600418.mb7550e0914, ISBN 978-3527600410

[1] Merck Index, 11th Edition, 9625.

[2] IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-62.2.2.1". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.

[Swift-3] Swift, Elijah; Hochanadel, Helen Phillips (May 1945). "The Vapor Pressure of Trimethylamine from 0 to 40°". Journal of the American Chemical Society. 67 (5): 880–881. doi:10.1021/ja01221a508.

[PGCH-4] NIOSH Pocket Guide to Chemical Hazards. "#0636". National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-5] Cite error: The named reference Ullmann was invoked but never defined (see the help page).

[Ashford's_Dictionary_of_Industrial-6] Ashford, Robert D. (2011). Ashford's Dictionary of Industrial Chemicals (3rd ed.). Wavelength. p. 9362. ISBN 978-0-9522674-3-0.

[:0-7] "Trimethylamine [MAK Value Documentation, 1983]", The MAK-Collection for Occupational Health and Safety, Wiley-VCH Verlag GmbH & Co. KGaA, 27 October 2014, pp. 1–9, doi:10.1002/3527600418.mb7550e0914, ISBN 978-3527600410

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