Dimethylaniline

N,N-Dimethylaniline
	Template:Chembox image sbs cell
Template:Longitem	Template:Unbulleted list
ChEBI	Template:Unbulleted list
ChemSpider	Template:Unbulleted list
DrugBank	Template:Unbulleted list
EC Number	Template:Unbulleted list
KEGG	Template:Unbulleted list
Template:Longitem	Template:Unbulleted list
RTECS number	Template:Unbulleted list
	Script error: No such module "collapsible list".
	Script error: No such module "collapsible list".
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Colorless liquid
Odor	amine-like
Density	0.956 g/mL
Melting point	Template:Chembox CalcTemperatures
Boiling point	Template:Chembox CalcTemperatures
Vapor pressure	1 mmHg (20°C)
Template:Longitem	−89.66·10−6 cm3/mol

Script error: No such module "about". <templatestyles src="Chembox/styles.css"/>

Template:Chembox AllOtherNames Template:Chembox headerbar Template:Chembox Indexlist Template:Chembox Jmol Template:Chembox ChEMBL Template:Chembox ECHA Template:Chembox E number Template:Chembox IUPHAR ligand Template:Chembox UNII Template:Chembox CompTox Template:Chembox headerbar Template:Chembox SolubilityInWater Template:Chembox Hazards Template:Chembox Datapage check Template:Yesno

Template:Chembox Footer/tracking container onlyScript error: No such module "TemplatePar".Template:Short description

N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.

Preparation

DMA was first reported in 1850 by the German chemist A. W. Hofmann, who prepared it by heating aniline and iodomethane:^[2]^[3]

C₆H₅NH₂ + 2 CH₃I → C₆H₅N(CH₃)₂ + 2 HI

DMA is produced industrially by alkylation of aniline with methanol in the presence of an acid catalyst:^[4]

C₆H₅NH₂ + 2 CH₃OH → C₆H₅N(CH₃)₂ + 2 H₂O

Similarly, it is also prepared using dimethyl ether as the methylating agent.

Reactions

Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles.^[5]

It is nitrated to produce tetryl, a derivative with four nitro groups which was once used as explosive. In acidic solution, the initial nitration gives 3-nitrodimethylaniline.^[6] It reacts with butyllithium to give the 2-lithio derivative. Electrophilic methylating agents like dimethyl sulfate attack the amine to give the quaternary ammonium salt:^[7]

C₆H₅N(CH₃)₂ +(CH₃O)₂SO₂ → C₆H₅N(CH₃)₃CH₃OSO₃

Diethylaniline and dimethylaniline are both used as acid-absorbing bases.

Applications

DMA is a key precursor to commercially important triarylmethane dyes such as malachite green and crystal violet.^[8] DMA serves as a promoter in the curing of polyester and vinyl ester resins.^[9] DMA is also used as a precursor to other organic compounds. A study of the in vitro metabolism of N,N-dimethylaniline using guinea pig and rabbit preparations and GLC techniques has confirmed N-demethylation and N-oxidation as metabolic pathways, and has also established ring hydroxylation as a metabolic route.^[10]

References

↑ ^a ^b Cite error: Script error: No such module "Namespace detect".Script error: No such module "Namespace detect".
↑ Watts, Henry, A Dictionary of Chemistry and the Allied Branches of Other Sciences, Part 2, (London, England: Longmans, Green, and Co., 1881), Methylanilines, p. 1306
↑
In 1850, August Hofmann announced his synthesis of methylaniline:
- Hofmann, A. W. (1850) "Researches regarding the molecular constitution of the volatile organic bases," Philosophical Transactions of the Royal Society of London, 140 : 93–131 ; see especially pp. 113-114.
However, in 1877, the Swiss chemist Alfred Kern (1850–1893) contended that Hofmann's reaction produced only dimethylaniline, not methylaniline:
- Kern, A. (1877) "Ueber die Darstellung von Monomethylanilin" (On the preparation of monomethylaniline), Berichte der deutschen chemischen Gesellschaft, 10 : 195–199.
Hofmann found that acetic anhydride reacted only with methylaniline, not with dimethylaniline, and was thus able to show that his reaction produced both the mono- and di-methylated forms of aniline:
- Hofmann, A. W. (1877) "Versuche über die Einwirkung des Chlor-, Brom- und Jodmethyls auf Anilin" (Experiments on the reaction of methyl chloride, bromide and iodide with aniline), Berichte der deutschen chemischen Gesellschaft, 10 : 591–601.
↑ Kahl, Thomas et al. (2007) "Aniline" in Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York. Script error: No such module "CS1 identifiers".
↑ Script error: No such module "Citation/CS1".
↑ Script error: No such module "Citation/CS1"..
↑ Script error: No such module "Citation/CS1"..
↑ Gessner, Thomas and Mayer, Udo (2002) "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH, Weinheim.Script error: No such module "CS1 identifiers".
↑ General Info on DMA (N,N-Dimethylaniline), Composites Australia
↑ Script error: No such module "Citation/CS1".

Script error: No such module "Check for unknown parameters".

[PGCH-1] Cite error: Script error: No such module "Namespace detect".Script error: No such module "Namespace detect".

[2] Watts, Henry, A Dictionary of Chemistry and the Allied Branches of Other Sciences, Part 2, (London, England: Longmans, Green, and Co., 1881), Methylanilines, p. 1306

[3] In 1850, August Hofmann announced his synthesis of methylaniline:
Hofmann, A. W. (1850) "Researches regarding the molecular constitution of the volatile organic bases," Philosophical Transactions of the Royal Society of London, 140 : 93–131 ; see especially pp. 113-114.
However, in 1877, the Swiss chemist Alfred Kern (1850–1893) contended that Hofmann's reaction produced only dimethylaniline, not methylaniline:
Kern, A. (1877) "Ueber die Darstellung von Monomethylanilin" (On the preparation of monomethylaniline), Berichte der deutschen chemischen Gesellschaft, 10 : 195–199.
Hofmann found that acetic anhydride reacted only with methylaniline, not with dimethylaniline, and was thus able to show that his reaction produced both the mono- and di-methylated forms of aniline:
Hofmann, A. W. (1877) "Versuche über die Einwirkung des Chlor-, Brom- und Jodmethyls auf Anilin" (Experiments on the reaction of methyl chloride, bromide and iodide with aniline), Berichte der deutschen chemischen Gesellschaft, 10 : 591–601.

[4] Hofmann, A. W. (1850) "Researches regarding the molecular constitution of the volatile organic bases," Philosophical Transactions of the Royal Society of London, 140 : 93–131 ; see especially pp. 113-114.

[5] Kern, A. (1877) "Ueber die Darstellung von Monomethylanilin" (On the preparation of monomethylaniline), Berichte der deutschen chemischen Gesellschaft, 10 : 195–199.

[6] Hofmann, A. W. (1877) "Versuche über die Einwirkung des Chlor-, Brom- und Jodmethyls auf Anilin" (Experiments on the reaction of methyl chloride, bromide and iodide with aniline), Berichte der deutschen chemischen Gesellschaft, 10 : 591–601.

[Ullmann-4] Kahl, Thomas et al. (2007) "Aniline" in Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York. Script error: No such module "CS1 identifiers".

[5] Script error: No such module "Citation/CS1".

[6] Script error: No such module "Citation/CS1"..

[7] Script error: No such module "Citation/CS1"..

[8] Gessner, Thomas and Mayer, Udo (2002) "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH, Weinheim.Script error: No such module "CS1 identifiers".

[9] General Info on DMA (N,N-Dimethylaniline), Composites Australia

[10] Script error: No such module "Citation/CS1".

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

Dimethylaniline

Contents

Preparation

Reactions

Applications

References

Navigation menu

Dimethylaniline

Preparation

Reactions

Applications

References

Navigation menu

Search