N , N -dimethyl- p -toluidine

Structural formula
General
Surname	N , N -dimethyl- p -toluidine
other names	N , N , 4-trimethylaniline 4- (dimethylamino) toluene 4-dimethyl aminotoluene, 4-dimethyl- p -toluidine N , N -dimethyl- para -toluidine p -methyldimethylaniline DMPT
Molecular formula	C 9 H 13 N
Brief description	light yellow to brown liquid with a characteristic odor
External identifiers / databases
CAS number 99-97-8 EC number 202-805-4 ECHA InfoCard 100.002.551 PubChem 7471 ChemSpider 7191 Wikidata Q2051705
properties
Molar mass	135.21 g mol −1
Physical state	liquid
density	0.94 g cm −3
Melting point	−15 ° C
boiling point	211 ° C
Vapor pressure	0.1 hPa (20 ° C)
solubility	very sparingly soluble in water (0.65 g l −1 at 37 ° C) miscible with ethanol , ether and chloroform
Refractive index	1.546 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 301-311-331-373-412 P: 261-273-280-301 + 310-311
Toxicological data	1.4 mg / l / 4 h ( LC 50 ,  rat ,  inh. ) 1650 mg / kg ( LD 50 ,  rat ,  oral )
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 -dimethyl-p-toluidine is a chemical compound from the aminobenzenes group .

Extraction and presentation

N , N -dimethyl- p -toluidine can be obtained by reacting p -toluidine , methyl iodide and sodium carbonate . In general, there are several processes for the preparation of N- alkyltoluidines, including N , N -dimethyl- p -toluidine, such as, for example, the acid-catalyzed alkylation of unalkylated toluidines with lower unbranched alcohols or ethers. Another method is reductive alkylation with lower aldehydes or ketones using metal catalysts under hydrogen pressure.

properties

N , N -Dimethyl- p -toluidine is a flammable, hardly inflammable, oily, light yellow to brown liquid with a characteristic odor, which is very sparingly soluble in water. It turns red-brown when exposed to light and air.

use

N , N -dimethyl- p -toluidine is used as a polymerization catalyst for polyester , acrylate and epoxy resins . It is also used as a hardener for dental cements and in adhesives. It is used as an intermediate for photo chemicals, in industrial adhesives, in artificial fingernail preparations, dyes and pharmaceuticals. It reacts with vinyl ethers in the presence of copper (II) chloride to form tetrahydroquinolines . The compound is also commercially available in solutions of plasticizers or styrene .

safety instructions

The vapors of N , N -dimethyl- p -toluidine can form an explosive mixture with air ( flash point 83 ° C, ignition temperature 425 ° C). An allergic reaction to dental materials containing N , N- dimethyl-p-toluidine is known in individual cases .

Individual evidence

1. ↑ ^{a b c d e f g h i j k l} Entry on N, N-dimethyl-p-toluidine in the GESTIS substance database of the IFA , accessed on November 6, 2018(JavaScript required) .
2. ↑ ^{a b} Data sheet N, N-Dimethyl-p-toluidine, 99% from AlfaAesar, accessed on November 6, 2018 ( PDF )(JavaScript required) .
3. ↑ Data sheet 4, N, N-Trimethylaniline, 99% from Sigma-Aldrich , accessed on November 6, 2018 ( PDF ).
4. ↑ Entry on N, N-dimethyl-p-toluidine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 6, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Data sheet N, N-dimethyl-p-toluidine (PDF) from Merck , accessed on November 6, 2018.
6. ↑ IARC Monographs: N, N-DIMETHYL-P-TOLUIDINE , accessed November 6, 2018.
7. ↑ ^{a b} GisChem: N , N -dimethyl-p-toluidine , accessed on November 6, 2018.
8. ^ GLA Verschueren, DP Bruynzeel: Allergy to N, N-dimethyl-p-toluidine in dental materials. In: Contact Dermatitis . 24, 1991, p. 149, doi : 10.1111 / j.1600-0536.1991.tb01680.x .