119516-83-5

Usage

Uses

1. Used in Hair Dye Industry:
1,4-Benzene-d4-diamine is used as a hair dye component for its ability to produce a range of colors when combined with other chemicals in the hair dye formulation. It serves as a contact allergen, which helps in the formation of the desired color upon oxidation.
2. Used in Pharmaceutical Industry:
1,4-Benzene-d4-diamine is used as a building block for the synthesis of various pharmaceutical compounds. Its chemical properties make it a versatile starting material for the development of new drugs with potential applications in the treatment of various diseases.
3. Used in Chemical Research:
Due to its unique deuterated structure, 1,4-Benzene-d4-diamine is used in chemical research as a stable isotope-labeled compound. This allows researchers to study the behavior of the molecule in various chemical reactions and processes, providing valuable insights into its properties and potential applications.
4. Used in Inflammatory Disease Treatment:
1,4-Benzene-d4-diamine, specifically as paraphenylenediamine, is used as a contact allergen for the treatment of inflammatory diseases. Its allergenic properties can help in modulating the immune response and provide relief from inflammation in certain conditions.

InChI:InChI=1/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2/i1D,2D,3D,4D

Upstream product

• 624-18-0 benzene-1,4-diamine hydrochloride 
• 106-50-3 1,4-phenylenediamine 

Downstream Products

• 1303947-00-3 C₂₁H₁₈⁽²⁾H₃N₃O₆ 
• 1303946-99-7 C₁₂H₁₂⁽²⁾H₄N₂O₄ 

Relevant academic research and scientific papers

Scalable and selective deuteration of (hetero)arenes

Isotope labelling, particularly deuteration, is an important tool for the development of new drugs, specifically for identification and quantification of metabolites. For this purpose, many efficient methodologies have been developed that allow for the small-scale synthesis of selectively deuterated compounds. Due to the development of deuterated compounds as active drug ingredients, there is a growing interest in scalable methods for deuteration. The development of methodologies for large-scale deuterium labelling in industrial settings requires technologies that are reliable, robust and scalable. Here we show that a nanostructured iron catalyst, prepared by combining cellulose with abundant iron salts, permits the selective deuteration of (hetero)arenes including anilines, phenols, indoles and other heterocycles, using inexpensive D2O under hydrogen pressure. This methodology represents an easily scalable deuteration (demonstrated by the synthesis of deuterium-containing products on the kilogram scale) and the air- and water-stable catalyst enables efficient labelling in a straightforward manner with high quality control. [Figure not available: see fulltext.].

EPR and ENDOR spectroscopic study of the reactions of aromatic azides with gallium trichloride

The reactions of gallium trichloride with phenyl and deuterio-phenyl azides, as well as with 4-methoxyphenyl azide and deuterium isotopomers, were examined by product analysis, CW EPR spectroscopy and pulsed ENDOR spectroscopy. The products included the corresponding anilines together with 4-aminodiphenylamine type dimers, and polyanilines. Complex CW EPR spectra of the radical cations of the dimers [ArNHC6H4NH 2]+ and trimers [ArNHC6H4NHC 6H4NH2]+ were obtained. These EPR spectra were analysed with the help of data from the deuterium-substituted analogues as well as the pulse Davies ENDOR spectra. DFT computations of the radical cations provided corroborating evidence and suggested the unpaired electrons were accommodated in extensive π-delocalised orbitals. A mechanism to account for the reductive conversion of aromatic azides to the corresponding anilines and thence to the dimers and trimers is proposed.