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Diethylammonium chloride

Dimethylamine
Skeletal formula of dimethylamine
Ball and stick model of dimethylamine
Names
Preferred IUPAC name
N-Methylmethanamine
Other names
(Dimethyl)amine
(The name dimethylamine is deprecated.)
Identifiers
3D model (JSmol)
3DMet B00125
605257
ChEBI
ChemSpider
ECHA InfoCard 100.004.272
EC Number 204-697-4
849
KEGG
MeSH dimethylamine
PubChem CID
RTECS number IP8750000
UNII
UN number 1032
Properties
(CH3)2NH
Molar mass 45.09 g·mol−1
Appearance Colorless gas
Odor Fishy, ammoniacal
Density 649.6 kg m−3 (at 25 °C)
Melting point −93.00 °C; −135.40 °F; 180.15 K
Boiling point 7 to 9 °C; 44 to 48 °F; 280 to 282 K
3.540 kg L−1
log P −0.362
Vapor pressure 170.3 kPa (at 20 °C)
310 μmol Pa−1 kg−1
Basicity (pKb) 3.29
Thermochemistry
−21–−17 kJ 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
H220, H302, H315, H318, H332, H335
P210, P261, P280, P305+351+338
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine 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 −6 °C (21 °F; 267 K) (liquid)
401 °C (754 °F; 674 K)
Explosive limits 2.8–14.4%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
698 mg/kg (rat, oral)
316 mg/kg (mouse, oral)
240 mg/kg (rabbit, oral)
240 mg/kg (guinea pig, oral)
4700 ppm (rat, 4 hr)
4540 ppm (rat, 6 hr)
7650 ppm (mouse, 2 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 10 ppm (18 mg/m3)
REL (Recommended)
TWA 10 ppm (18 mg/m3)
IDLH (Immediate danger)
500 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

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. In 2005, an estimated 270,000 tons were produced industrially, but it is also found as a natural product.

The molecule consists of a nitrogen atom with two methyl substituents and one proton. Dimethylamine is a weak base and the pKa of the ammonium salt CH3-NH2+-CH3 is 10.73, a value above methylamine (10.64) and trimethylamine (9.79).

Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by catalytic reaction of methanol and ammonia at elevated temperatures and high pressure:

Dimethylamine is found quite widely distributed in animals and plants, and is present in many foods at the level of a few mg/kg.

Dimethylamine is a precursor to several industrially significant compounds. It reacts with carbon disulfide to give dimethyl dithiocarbamate, a precursor to a family of chemicals widely used in the vulcanization of rubber. The solvents dimethylformamide and dimethylacetamide are derived from dimethylamine. It is raw material for the production of many agrichemicals and pharmaceuticals, such as dimefox and diphenhydramine, respectively. The chemical weapon tabun is derived from dimethylamine. The surfactant lauryl dimethylamine oxide is found in soaps and cleaning compounds. Unsymmetrical dimethylhydrazine, a rocket fuel, is prepared from dimethylamine.


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