Dimethyl-4-phenylenediamine

Dimethyl-4-phenylenediamine
Names
	IUPAC name N,N-Dimethylbenzene-1,4-diamine
	Other names p-Aminodimethylaniline; N,N-Dimethyl-p-phenylenediamine; 4-(Dimethylamino)aniline; p-Amino-N,N-dimethylaniline; p-(Dimethylamino)aniline; DMPPDA; Dimethyl-p-phenylenediamine; 4-Amino-N,N-dimethylaniline; p-Dimethylaminophenylamine; DMPD
Identifiers
CAS Number	99-98-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	13884246 ;
ECHA InfoCard	100.002.552
PubChem CID	7472;
UNII	7GZH2FMK7X ;
CompTox Dashboard (EPA)	DTXSID6025149 ;
	SMILES CN(C)C1=CC=C(C=C1)N;
Properties
Chemical formula	C8H12N2
Molar mass	136.198 g·mol−1
Appearance	Reddish-violet crystals[1]
Melting point	53 °C (127 °F; 326 K)[1]
Boiling point	262 °C (504 °F; 535 K)[1]
	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

Dimethyl-4-phenylenediamine is an amine. It has been used as an accelerator for the vulcanization of rubber.[2] It can be used in oxidase tests.

Synthesis

Dimethyl-4-phenylenediamine is made by the nitrosylation of dimethylaniline followed by reduction.

Applications

Dimethyl-4-phenylenediamine can be converted to methylene blue by reaction with dimethylaniline and sodium thiosulfate in several steps:[3]

It is used as accelerator for the vulcanization of rubber, being first converted to the corresponding mercaptobenzothiazole.

gollark: Testbot says you're down.

gollark: Yes, I *am* portforwarding 6667. How apiometacontracontraformic!

gollark: ... am I actually portforwarding 6667.

gollark: ```16:41 -!- Irssi: Looking up irc.osmarks.net16:41 -!- Irssi: Connecting to irc.osmarks.net [86.171.125.104] port 669716:41 -!- Irssi: Connection to irc.osmarks.net established16:41 -!- Irssi: warning Connection reset by peer16:41 -!- Irssi: Connection lost to irc.osmarks.net```Unfathomable!

gollark: I was mostly concerned about the SSL enablement on *my* end exploding somehow.

References

Merck Index, 11th Edition, 3242
Geer, W. C.; Bedford, C. W. (January 24, 1925). "The History of Organic Accelerators in the Rubber Industry". Industrial and Engineering Chemistry. 17 (4): 393–396. doi:10.1021/ie50184a021.
Horst Berneth (2012). "Azine Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_213.pub3.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[Merck-1] Merck Index, 11th Edition, 3242

[2] Geer, W. C.; Bedford, C. W. (January 24, 1925). "The History of Organic Accelerators in the Rubber Industry". Industrial and Engineering Chemistry. 17 (4): 393–396. doi:10.1021/ie50184a021.

[3] Horst Berneth (2012). "Azine Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_213.pub3.