N , N -dimethylaniline

Structural formula
General
Surname	N , N -dimethylaniline
other names	Dimethylaminobenzene; Dimethyl-phenyl-amine;
Molecular formula	C 8 H 11 N
Brief description	colorless to yellowish liquid with an amine-like odor
External identifiers / databases
EC number	204-493-5
ECHA InfoCard	100.004.085
PubChem	949
ChemSpider	924
Wikidata	Q310473
properties
Molar mass	121.18 g mol −1
Physical state	liquid
density	0.96 g cm −3
Melting point	2 ° C
boiling point	194 ° C
Vapor pressure	49.6 h Pa (100 ° C)
solubility	poor in water (1.2 g l −1 at 20 ° C); soluble in ethanol , diethyl ether , chloroform , acetone and benzene ;
Refractive index	1.5583 (20 ° C)
safety instructions
H and P phrases	H: 351-301-311-331-411
	P: 261-273-280-301 + 310 + 330-302 + 352-312-403 + 233
MAK	DFG / Switzerland: 5 ml m −3 or 25 mg m −3
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

N , N -dimethylaniline is a mostly yellowish oily liquid with a characteristic odor, which quickly turns dark in air. The compound is basic and forms salts with acids.

Manufacturing

N , N -dimethylaniline can be achieved by methylation of aniline with methanol under acid catalysis to produce:

Instead of using two equivalents of methanol, one equivalent of dimethyl ether can also be used.

use

In the chemical industry, N , N -dimethylaniline is primarily used as a starting material for the synthesis of dyes such as methyl orange and synthesis intermediates. DMA is also used as a reducing component in connection with organic peroxides (often also referred to as accelerators or activators) for the polymerization / curing of unsaturated polyesters (UP resins). A typical application for such products are e.g. B. fillers (repair fillers ) for car bodies or natural stones ( marble ).

Toxicity

N , N -dimethylaniline is a toxic compound, can also be absorbed through the skin and is suspected of causing cancer . Vapors of N , N -dimethylaniline should not be inhaled. The first signs of poisoning by oral intake are often dizziness, vomiting and impaired cognition.

Individual evidence

↑ ^a ^b entry on N, N-dimethylaniline. In: Römpp Online . Georg Thieme Verlag, accessed on September 29, 2014.
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on N, N-dimethylaniline in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-192.
↑ Entry on N, N-dimethylaniline in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 121-69-7 or N, N-dimethylaniline ), accessed on November 2, 2015.

[roempp-1] try on N, N-dimethylaniline. In: Römpp Online . Georg Thieme Verlag, accessed on September 29, 2014.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on N, N-dimethylaniline in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CRC90_3_192-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-192.

[CLP_100.004.085-4] Entry on N, N-dimethylaniline in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 121-69-7 or N, N-dimethylaniline ), accessed on November 2, 2015.