N,N-Dimethylphenylenediamine

Last updated
N,N-Dimethylphenylenediamine
N,N-dimethyl-p-phenylenediamine.svg
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.552 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-807-5
KEGG
PubChem CID
UNII
UN number 2811 (DIMETHYL-P-PHENYLENEDIAMINE)
  • InChI=1S/C8H12N2/c1-10(2)8-5-3-7(9)4-6-8/h3-6H,9H2,1-2H3
    Key: BZORFPDSXLZWJF-UHFFFAOYSA-N
  • CN(C)C1=CC=C(C=C1)N
Properties
C8H12N2
Molar mass 136.198 g·mol−1
Appearancecolorless 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:
GHS-pictogram-skull.svg
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

Contents

Structure of Wurster's Red bromide with bond distances in picometers Wurster'sRedBromide.svg
Structure of Wurster's Red bromide with bond distances in picometers

Synthesis

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

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

Synthesis of methylene blue.png

It reacts with carbon disulfide to give the corresponding mercaptobenzothiazole:

(CH3)2NC6H4NH2 + CS2 + S → (CH3)2NC6H3NCSH)S + H2S

History

Casmir Wurster discovered tetramethylphenylenediamine and its easy oxidation. [5] Subsequent work revealed the variety of redox properties of the phenylenediamines. [6]

References

  1. 1 2 Merck Index , 11th Edition, 3242
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ Horst Berneth (2012). "Azine Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_213.pub3. ISBN   9783527303854.
  5. ↑ 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.
  6. ↑ 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.
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