Welcome to LookChem.com Sign In|Join Free
  • or

Encyclopedia

p-Phenylenediamine

Base Information
  • Chemical Name:p-Phenylenediamine
  • CAS No.:106-50-3
  • Deprecated CAS:56481-76-6,82785-55-5
  • Molecular Formula:C6H8N2
  • Molecular Weight:108.143
  • Hs Code.:292151
  • European Community (EC) Number:203-404-7
  • ICSC Number:0805
  • NSC Number:4777
  • UN Number:1673
  • UNII:U770QIT64J
  • DSSTox Substance ID:DTXSID9021138
  • Nikkaji Number:J4.035E
  • Wikipedia:P-Phenylenediamine
  • Wikidata:Q415024
  • Metabolomics Workbench ID:52565
  • ChEMBL ID:CHEMBL403741
  • Mol file:106-50-3.mol
p-Phenylenediamine

Synonyms:1,4-benzenediamine;1,4-phenyldiamine;1,4-phenylenediamine;4-phenylenediamine;4-phenylenediamine bromide, ion(1+);4-phenylenediamine dihydrochloride;4-phenylenediamine diperchlorate;4-phenylenediamine ion (1+);4-phenylenediamine monohydrobromide;4-phenylenediamine monohydrochloride;4-phenylenediamine monohydroiodide;4-phenylenediamine monooxalate;4-phenylenediamine monoperchlorate;4-phenylenediamine monosulfate;4-phenylenediamine sulfate;black henna;p-phenylenediamine;para-phenylenediamine;paraphenylenediamine;Ursol-D

Suppliers and Price of p-Phenylenediamine
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • 1,4-Phenylenediamine
  • 10g
  • $ 75.00
  • TCI Chemical
  • 1,4-Phenylenediamine >98.0%(GC)(T)
  • 25g
  • $ 19.00
  • TCI Chemical
  • 1,4-Phenylenediamine >98.0%(GC)(T)
  • 250g
  • $ 55.00
  • Sigma-Aldrich
  • p-Phenylenediamine anti-fade reagent
  • 250g
  • $ 65.30
  • Sigma-Aldrich
  • p-Phenylenediamine anti-fade reagent
  • 1g
  • $ 82.90
  • Sigma-Aldrich
  • p-Phenylenediamine anti-fade reagent
  • 100g
  • $ 54.60
  • Sigma-Aldrich
  • p-Phenylenediamine solution certified reference material, 2000 μg/mL in methylene chloride
  • 48298
  • $ 37.10
  • Sigma-Aldrich
  • 1,4-Phenylenediamine for synthesis. CAS 106-50-3, pH 9 (50 g/l, H O, 20 °C)., for synthesis
  • 8072460250
  • $ 36.30
  • Sigma-Aldrich
  • 1,4-Phenylenediamine for synthesis
  • 250 g
  • $ 34.78
  • Sigma-Aldrich
  • 1,4-Phenylenediamine for synthesis. CAS 106-50-3, pH 9 (50 g/l, H O, 20 °C)., for synthesis
  • 8072460005
  • $ 22.20
Total 43 raw suppliers
Chemical Property of p-Phenylenediamine
Chemical Property:
  • Appearance/Colour:white to light purple solid 
  • Vapor Pressure:0.00817mmHg at 25°C 
  • Melting Point:139 °C 
  • Refractive Index:1.66 
  • Boiling Point:267.4 °C at 760 mmHg 
  • PKA:4.17(at 25℃) 
  • Flash Point:135.9 °C 
  • PSA:52.04000 
  • Density:1.15 g/cm3 
  • LogP:2.01340 
  • Storage Temp.:2-8°C 
  • Solubility.:Soluble in alcohol, chloroform, ether and hot benzene. 
  • Water Solubility.:47 g/L (25℃) 
  • XLogP3:-0.3
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:0
  • Exact Mass:108.068748264
  • Heavy Atom Count:8
  • Complexity:54.9
  • Transport DOT Label:Poison
Purity/Quality:

99% *data from raw suppliers

1,4-Phenylenediamine *data from reagent suppliers

Safty Information:
  • Pictogram(s): ToxicT,DangerousN,VeryT+,HarmfulXn 
  • Hazard Codes: T:Toxic;
  • Statements: R23/24/25:; R36:; R43:; R50/53:; 
  • Safety Statements: S28A:; S36/37:; S45:; S60:; S61:; 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Nitrogen Compounds -> Amines, Aromatic
  • Canonical SMILES:C1=CC(=CC=C1N)N
  • Recent EU Clinical Trials:An open label, intra-subject, controlled multi-centre study to assess the concordance (specificity and sensitivity) between Colourstart? Test 73 mcg Cutaneous Patch and Finn Chamber in the detection of para-Phenylenediamine (PPD) allergy in subjects with known or clinically suspected allergy and those with no known allergy.
  • Inhalation Risk:A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
  • Effects of Short Term Exposure:The substance is irritating to the eyes. Inhalation of dust may cause asthmatic reactions. Ingestion could cause swelling of mouth and throat. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Exposure could cause death.
  • Effects of Long Term Exposure:Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma. The substance may have effects on the kidneys. This may result in kidney impairment.
  • Description P-phenylenediamine is one of the simplest aromatic diamine with the pure product being white to purple red crystals. It turns purple or dark brown color when being exposed to the air. It is slightly soluble in cold water, soluble in alcohol, ether, chloroform and benzene. It can be used for making azo dyes, high-molecule polymers and can also be used for the production of fur dyes, rubber antioxidants and photo developer and is mainly used for Kevlar, azo dyes, sulfur dyes, acid dyes as well as being used for the production of black fur D, black fur DB, brown fur N2 as well as rubber antioxidant DNP, DOP and MB. It can also be used as the raw material of cosmetic hair p-Phenylenediamine series, gasoline polymerization inhibitor and developer. P-phenylenediamine, as a chemical dye, is currently permitted for use in hair dye production, but there is a clear usage limits. According to China "Hygienic Standard for Cosmetics," the content of p-phenylenediamine in hair dyes should not exceed 6%. According to the introduction of experts, although five kinds of "Yixihei" shampoo have their p-phenylenediamine content being within 1.1% to 1.4%. However, the shampoo has high frequency of usage with long-term accumulation being prone to pose a threat to the health and safety of consumers. There is still no literatures regarding to whether phenylenediamine is carcinogenic or not; but there is literature basis regarding to that p-phenylenediamine drug is toxic organic. We can refer to Shanghai Science and technology press (November 1985) "reagent Handbook" (second edition), page 980. Overseas research has shown that for population being subject to frequent hair dying has the incidence of breast cancer, skin cancer and leukemia increased. In addition, p-phenylenediamine is also a common sensitive reagent for testing iron and copper. In the international arena, it is also used for aircraft coatings, bullet-proof clothing intima and walls paint. p-phenylenediamine structure Paraphenylenediamine (PPD) is a colorless compound oxidized by hydrogen peroxide in the presence of ammonia. It is then polymerized by a coupling agent to produce a color.
  • Uses P-phenylenediamine is important dye intermediates and is mainly used in the manufacture of dyes and sulfur dyes; it can also be used for the production of fur black D and rubber antioxidant DNP, 288, DOP, DBP etc. P-phenylenediamine can also be used as the raw material of cosmetic hair dye “WuErsi D”, gasoline polymerization inhibitor and developer. p-Phenylenediamine is used for dyeing hairand fur, in the manufacture of azo dyes, inaccelerating vulcanization of rubber, and inantioxidants. A hair dye component, paraphenylenediamine, as a contact allergen for treatment of inflammatory diseases. 4-Phenylenediamine is an azo-dye intermediate; photographic-developing agent; photo-chemical measurements; intermediate in manufacture of antioxidants and accelerators for rubber; laboratory reagent; dye for hair and fur; lithography; photocopying; oils; greases; gasoline; antioxidant/accelerator in the rubber and plastic industry; the hydrochloride is used as blood reagent.
  • Production method It can be obtained from the reduction of P-nitroaniline via iron in acid medium. Put the iron into hydrochloric acid and heat to 90 °C. Add with stirring of p-nitroaniline. After completion of the adding, have them reacted at 95-100 ℃ for 0.5h, and then add drop wise of concentrated hydrochloric acid so that the reduction reaction is completed. After cooling, use saturated sodium carbonate solution for neutralizing to PH7-8, after boiling and have hot filtration; use host water to wash the filter cake. The filtrate and washings were combined and subject to concentration under reduced pressure; after cooling crystallization or vacuum distillation, we can obtain the p-phenylenediamine with the yield of being 95%.
  • Physical properties White, red, or brown crystals. May darken on exposure to air.
Technology Process of p-Phenylenediamine

There total 287 articles about p-Phenylenediamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With tris(triphenylphosphine)ruthenium(II) chloride; formic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; at 20 - 25 ℃; for 0.5h; Product distribution; selective reduction with a new hydrogen source;
Guidance literature:
With graphitic carbon nitride; hydrazine hydrate; In water; at 70 ℃; for 8h; chemoselective reaction; Irradiation; Sealed tube; Green chemistry;
DOI:10.1002/asia.201800515
Guidance literature:
With triethylsilane; indium(III) chloride; In acetonitrile; at 0 ℃; for 0.25h;
DOI:10.1021/ol0606637
Refernces

DFT and experimental study of N,N'-bis(3'-carboxy,4'-aminophenyl)-1,4- quinonediimine, a carboxyl substituted aniline trimer

10.1016/j.molstruc.2010.05.038

The study presents a density functional theory (DFT) and experimental investigation of N,N'-bis(3-carboxy,4'-aminophenyl)-1,4-quinonediimine, a carboxyl-substituted aniline trimer. The research aims to understand the electronic and steric effects in co-polymers of aniline and anthranilic acid, and to explore the trimer's potential in corrosion inhibition. Chemicals used include 1,4-phenylenediamine, hydrochloric acid, ammonium persulfate, anthranilic acid, and ammonium hydroxide for the synthesis of the trimer. The synthesized trimer was then subjected to various experimental analyses, including UV-vis, near-IR, and NMR spectroscopy, to study its properties. The study also utilized computational methods to optimize the structures of the trimer's isomers and calculate their electronic properties, providing insights into the trimer's behavior in different oxidation states and solvent environments. The purpose of these chemicals was to synthesize the trimer and understand its redox properties, its ability to 'self-dope', and its effectiveness in corrosion inhibition, particularly in alkaline environments where standard oligo- and polyanilines fail.

Photosonoelectrochemical analysis of Lawsonia inermis (henna) and artificial dye used in tattoo and dye industry

10.1016/j.jphotochem.2018.04.026

The study focuses on the photosonoelectrochemical (PSEC) analysis of Lawsonia inermis (henna) and artificial dyes, specifically lawsone and p-Phenylenediamine (PPD), used in the tattoo and dye industry. The primary objective was to understand the degradation mechanisms and the formation of harmful byproducts when these dyes are exposed to conditions simulating those of tattoo ink application, such as UV irradiation, sonication, and electrochemical perturbations. The chemicals used in the study served various purposes: Lawsonia inermis was analyzed for its natural dye properties, lawsone as a major constituent of henna was examined for its electroactivity and degradation, and PPD, an artificial dye often added to henna for color enhancement, was assessed for its degradation products. The study aimed to demonstrate the potential harmfulness of using artificial dyes like PPD over natural dyes like henna in body art and dyeing applications.

Structure-biodistribution relation of neutral 99mTc(CO)3-complexes with tridentate N-substituted derivatives of aminoethylglycine and phenylenediamine

10.1016/j.tetlet.2006.04.136

The study investigates the structure-biodistribution relationship of neutral 99mTc(CO)3-complexes with tridentate N-substituted derivatives of aminoethylglycine (EDAA) and phenylenediamine (PDAA). The researchers synthesized and characterized a series of 99mTc-tricarbonyl complexes with varying lipophilicity by modifying the amines with uncharged substituents such as methyl, ethyl, butyl, or benzyl groups. These modifications aimed to influence the biodistribution of the complexes in mice, particularly their ability to cross the blood-brain barrier (BBB). The chemicals used included ethylenediamine-N-acetic acid (EDAA) and ortho-phenylenediamine-N-acetic acid (PDAA) derivatives, which served as ligands to form neutral complexes with the 99mTc(CO)3+-moiety. The purpose of these chemicals was to create radiopharmaceuticals for potential use in diagnosing and monitoring neurological diseases, with a focus on their ability to pass the BBB and be taken up by the brain.

Novel dendritic cores based on thiacalix[4]arene derivatives

10.1016/j.tetlet.2004.07.085

The research focuses on the design and synthesis of novel dendritic cores based on thiacalix[4]arene derivatives, which possess potential applications in supramolecular chemistry due to their unique properties such as complexation ability towards transition metals and chemical modifiability. The purpose of the study was to overcome the steric hindrance issues encountered during the derivatization of thiacalix[4]arene derivatives to create dendritic cores with amino surface groups. The researchers successfully applied a synthetic strategy that involved the use of benzylic spacers to withdraw carboxyl groups from the thiacalix[4]arene moiety, allowing for the realization of novel thiacalix[4]arenes bearing two or four protected lysine units. Key chemicals used in the process included thiacalix[4]arene tetraacids, oxalyl chloride, mono-Boc-protected 1,2-diaminoethane, mono-Boc-protected 1,4-phenylenediamine, methyl p-bromomethylbenzoate, and CDI (1,1,3,3-tetramethyluronium chloride).

Dimeric and trimeric molybdenum( II) complexes containing 2-substituted η3-bonded butadienyl bridging ligands

10.1016/s0022-328x(97)00456-7

The study investigates the formation of dimeric and trimeric molybdenum(II) complexes containing 2-substituted 3-bonded butadienyl bridging ligands. The starting material used is [MoCI(CO)2(@-CH2(COCI)C=CH2)phen] (phen = 1,10-phenanthroline) (1). When 1 reacts with 1,2-ethanediol or N,N'-diethylethylenediamine in a 2:1 mole ratio, dimeric complexes [MoCI(CO)2(@-CH/(COACH2)C=CH2)phen]2 are formed, where A represents the substituent group (A = O for ester, A = NEt for amide). Reactions with hydroquinone or 1,4-phenylenediamine yield monomeric complexes [MoCI(CO)2(@-CH2(COA)C=CH2)phen], while dimeric complexes are isolated from reactions involving 4,4'-ethylenedianiline or p-xylylenediamine. Attempts to prepare a novel complex bridged by three linked amide substituted butadienyl groups using diethylenetriamine were unsuccessful. However, reaction of 1 with triethanolamine or tris(2-aminoethyl)amine in a 3:1 mole ratio gives trimeric complexes [MoCI(CO)2(~/a-CH2(COACH2CH2)C=CH2)phen]3 N (A = O, NH) in good yield. The study establishes conditions for the formation of these complexes and examines the boundaries of dimer and trimer formation using various bifunctional and trifunctional reagents.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1 Customer Service

What can I do for you?
Get Best Price

Get Best Price for 106-50-3
  • ©2008 LookChem.com,License:ICP NO.:Zhejiang16009103 complaints:service@lookchem.com
  • [Hangzhou]86-0571-87562588,87562578,87562573 Our Legal adviser: Lawyer