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{{unreferenced|date=December 2008}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 351379068
| Watchedfields = changed
|ImageFile=Dimethylphenylenediamine.png
⚫ | verifiedrevid = 414584828
|ImageSize=200px
| ImageFile=N,N-dimethyl-p-phenylenediamine.svg
|IUPACName=N,N-dimethylbenzene-1,4-diamine
| PIN=''N''<sup>1</sup>,''N''<sup>1</sup>-Dimethylbenzene-1,4-diamine
|OtherNames=DMPD; 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 | OtherNames= ''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
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7192 | ChemSpiderID = 13884246
| CASNo_Ref = {{cascite}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=99-98-9 | CASNo=99-98-9
| UNII_Ref = {{fdacite|changed|FDA}}
⚫ | PubChem=7472
| UNII = 7GZH2FMK7X
⚫ | SMILES=CN(C)C1=CC=C(C=C1)N
⚫ | PubChem=7472
⚫ }}
⚫ | SMILES=CN(C)C1=CC=C(C=C1)N
⚫ }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| C=8 | H=12 | N=2
| Formula=C<sub>8</sub>H<sub>12</sub>N<sub>2</sub>
| Appearance=Reddish-violet crystals<ref name=Merck>'']'', 11th Edition, '''3242'''</ref>
| MolarMass=136.19428
| MeltingPtC = 53
| Appearance=
| MeltingPt_ref = <ref name=Merck/>
| Density=
| BoilingPtC= 262
| MeltingPt=
| BoilingPt_ref = <ref name=Merck/>
| BoilingPt=
⚫ }}
| Solubility=
⚫ }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
}}
}} }}


'''Dimethyl-4-phenylenediamine''' is an ]. It has been used as an accelerator for the vulcanization of rubber.<ref>{{cite journal |last1=Geer |first1=W. C. |last2=Bedford |first2=C. W. |date= January 24, 1925 |title= The History of Organic Accelerators in the Rubber Industry|journal= Industrial and Engineering Chemistry|volume= 17|issue= 4|pages= 393–396 |doi=10.1021/ie50184a021 |author1-link=William C. Geer }}</ref> It can be used in ]s.
'''Dimethyl-4-phenylenediamine''' is a molecule used in the ].


==Synthesis==
⚫ ]
Dimethyl-4-phenylenediamine is made by the ] of ] followed by reduction.


==Applications==
Dimethyl-4-phenylenediamine can be converted to ] by reaction with ] and ] in several steps:<ref>{{cite encyclopedia|author=Horst Berneth|title=Azine Dyes|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2012|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a03_213.pub3|isbn=9783527303854 }}</ref>


:]
{{organic-compound-stub}}


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

]
:]

==References==
{{reflist}}

⚫ ]
]
]

Latest revision as of 12:00, 3 July 2024

Dimethyl-4-phenylenediamine
Names
Preferred 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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.552 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • CN(C)C1=CC=C(C=C1)N
Properties
Chemical formula C8H12N2
Molar mass 136.198 g·mol
Appearance Reddish-violet crystals
Melting point 53 °C (127 °F; 326 K)
Boiling point 262 °C (504 °F; 535 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Dimethyl-4-phenylenediamine is an amine. It has been used as an accelerator for the vulcanization of rubber. 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:

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

References

  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. ISBN 9783527303854.
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