N,N-Dimethylphenylenediamine
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| Names | |
|---|---|
| Preferred IUPAC name
N1,N1-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 | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.552 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
| UN number | 2811 (DIMETHYL-P-PHENYLENEDIAMINE) |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H12N2 | |
| Molar mass | 136.198 g·mol−1 |
| Appearance | colorless solid |
| Density | 1.036 g/cm³ |
| Melting point | 53 °C (127 °F; 326 K)[1] |
| Boiling point | 262 °C (504 °F; 535 K)[1] |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H301, H311, H331 | |
| P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N,N-Dimethylphenylenediamine (dimethyl-4-phenylenediamine) is an organic compound with the formula H2NC6H4N(CH3)2. It is one of the phenylenediamines, a class of compounds that have long attracted attention for their redox properties. This diamine is, for example, easily oxidized to a deep red radical cation, [H2NC6H4N(CH3)2]+ which is called Wurster's Red.[2] The related Wurster's Blue cation has four N-methyl groups (CH3)2NC6H4N(CH3)+2
Synthesis
[edit]Dimethyl-4-phenylenediamine is prepared by the nitration of dimethylaniline followed by reduction of the resulting 4-nitrodimethylaniline. A variety of methods have been examined.[3]
Applications
[edit]Dimethyl-4-phenylenediamine can be converted to methylene blue by reaction with dimethylaniline and sodium thiosulfate in several steps:[4]
It reacts with carbon disulfide to give the corresponding mercaptobenzothiazole:
- (CH3)2NC6H4NH2 + CS2 + S → (CH3)2NC6H3NCSH)S + H2S
History
[edit]Casmir Wurster discovered tetramethylphenylenediamine and its easy oxidation.[5] Subsequent work revealed the variety of redox properties of the phenylenediamines.[6]
References
[edit]- 1 2 Merck Index, 11th Edition, 3242
- ↑ Tanaka, J.; Sakabe, N. (1968). "The crystal structure of Würster's red bromide". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 24 (10): 1345–1349. Bibcode:1968AcCrB..24.1345T. doi:10.1107/S0567740868004279.
- ↑ Jagadeesh, Rajenahally V.; Wienhöfer, Gerrit; Westerhaus, Felix A.; Surkus, Annette-Enrica; Pohl, Marga-Martina; Junge, Henrik; Junge, Kathrin; Beller, Matthias (2011). "Efficient and highly selective iron-catalyzed reduction of nitroarenes". Chemical Communications. 47 (39): 10972–10974. doi:10.1039/c1cc13728j. PMID 21897952.
- ↑ Horst Berneth (2012). "Azine Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_213.pub3. ISBN 9783527303854.
- ↑ Wurster, C.; Schobig, E. (1879). "Ueber die Einwirkung oxydirender Agentien auf Tetramethylparaphenylendiamin". Berichte der Deutschen Chemischen Gesellschaft. 12 (2): 1807–1813. doi:10.1002/cber.187901202156.
- ↑ L. Michaelis; M. P. Schubert; S. Granick (1939). "The Free Radicals of the Type of Wurster's Salts". J. Am. Chem. Soc. 61 (8): 1981–1992. Bibcode:1939JAChS..61.1981M. doi:10.1021/ja01877a013.