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CAS

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1,4-Diamino-2-nitrobenzene, also known as o-Nitro-paraphenylenediamine (ONPD), is a primary amino compound that features a p-phenylenediamine structure with one hydrogen atom on the benzene ring replaced by a nitro group. It is characterized by its dark red crystal or powder form and is known for its use as a hair dye and sensitizer in the hairdressing industry.

5307-14-2

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5307-14-2 Usage

Uses

Used in Hair and Fur Dye Industry:
1,4-Diamino-2-nitrobenzene is used as a dyestuff for coloring hair, particularly in semi-permanent and permanent hair coloring products. It is responsible for producing brown and red shades on the hair, making it a popular choice for various hair-dyeing preparations.
Used in Fur Dyeing:
In the fur industry, 1,4-Diamino-2-nitrobenzene is utilized as a dyestuff to dye furs in brown and reddish-brown shades, enhancing their appearance and adding value to the final product.

Air & Water Reactions

1,4-Diamino-2-nitrobenzene may be sensitive to prolonged exposure to light and air. Insoluble in water.

Reactivity Profile

1,4-Diamino-2-nitrobenzene is incompatible with strong oxidizing agents.

Fire Hazard

Flash point data for 1,4-Diamino-2-nitrobenzene are not available; however, 1,4-Diamino-2-nitrobenzene is probably combustible.

Flammability and Explosibility

Nonflammable

Contact allergens

ONPD is a hair dye and a sensitizer in hairdressers and consumers who are generally sensitive to PPD too.

Safety Profile

Suspected carcinogen with experimental carcinogenic and neoplastigenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.

Check Digit Verification of cas no

The CAS Registry Mumber 5307-14-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,0 and 7 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5307-14:
(6*5)+(5*3)+(4*0)+(3*7)+(2*1)+(1*4)=72
72 % 10 = 2
So 5307-14-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H7N3O2/c7-5-1-3-6(4-2-5)8-9(10)11/h1-4,8H,7H2

5307-14-2 Well-known Company Product Price

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  • Alfa Aesar

  • (B23477)  2-Nitro-p-phenylenediamine, 95%   

  • 5307-14-2

  • 25g

  • 332.0CNY

  • Detail
  • Alfa Aesar

  • (B23477)  2-Nitro-p-phenylenediamine, 95%   

  • 5307-14-2

  • 100g

  • 641.0CNY

  • Detail
  • Alfa Aesar

  • (B23477)  2-Nitro-p-phenylenediamine, 95%   

  • 5307-14-2

  • 500g

  • 2385.0CNY

  • Detail
  • Aldrich

  • (N21200)  2-Nitro-1,4-phenylenediamine  95%

  • 5307-14-2

  • N21200-100G

  • 1,120.86CNY

  • Detail
  • Aldrich

  • (N21200)  2-Nitro-1,4-phenylenediamine  95%

  • 5307-14-2

  • N21200-500G

  • 3,409.38CNY

  • Detail

5307-14-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-nitro-p-phenylenediamine

1.2 Other means of identification

Product number -
Other names 2-NPPD

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5307-14-2 SDS

5307-14-2Relevant articles and documents

Protonation of Cationic Bases in Perchloric Acid: Establishment of the H+ Scale in 0-11 M Perchloric Acid

Lovell, Michael W.,Vogt, Brian S.,Schulman, Stephen G.

, p. 1885 - 1888 (1984)

The protonation of several monocationic bases in perchloric acid was studied with UV-visible absorption spectroscopy.The H+ scale in perchloric acid was established by using primary amine cationic bases as indicators.It was found that the H+ scale in perchloric acid is more negative than in sulfuric acid.The acid-dissociation constants for compounds studied in both acids were found to be in reasonably good agreement with each other.

[1+1] Copper(II) macrocyclic Schiff base complex on rGO as a photocatalyst for reduction of nitroaromatics compounds under visible-light irradiation

Ghalebin, Saeed Nasiri,Bezaatpour, Abolfazl,Sadr, Moayad Hossaini,Sadjadi, Mirabdullah Seyed,Moghaddam, Mohammad Khodadadi,Szunerits, Sabine

, (2021/01/26)

In this work, [1 + 1] macrocyclic Copper(II) Schiff base complex ([CuL](NO3)2.H2O) was synthesized and grafted on reduced graphene oxide successfully. The novel prepared sample was characterized by physico-chemical techniques and used as a photocatalyst for the reduction of nitroaromatic compounds to their amine derivatives at room temperature under visible-light irradiation with hydrazine mono hydrate. From the prepared samples, reduced graphene oxide loaded with 30% [CuL](NO3)2.H2O catalyst (rGO/CuM30) shows the best efficiency for converting different nitroaromatic compounds to the corresponding amino compounds using visible light. As-prepared catalyst illustrated excellent activity for the reduction of 2-nitrophenol to 2-aminophenol (100% conversion) in only 90 min. Finally, the catalyst could be recovered for five times and reused without decreasing of its efficiency.

Gold supported on titania for specific monohydrogenation of dinitroaromatics in the liquid phase

Liu, Shuang-Shuang,Liu, Xiang,Yu, Lei,Liu, Yong-Mei,He, He-Yong,Cao, Yong

, p. 4162 - 4169 (2014/09/29)

Liquid-phase selective monohydrogenation of various substituted dinitroaromatics to the corresponding valuable nitroanilines was investigated on gold-based catalysts. Special attention was paid to the effect of Au particle size on this monoreduction reaction. Interestingly, TiO2 supported gold catalysts containing a relatively larger mean Au particle size (>5 nm) showed far superior chemoselectivity for specific mono-hydrogenation of dinitroaromatics, with the highest performance attainable for the catalyst bearing Au particles of ca. 7.5 nm. Results in the intermolecular competitive hydrogenation showed that the intrinsic higher accumulation rates of the desired nitroanilines associated with the catalyst possessing larger Au particles were responsible for the high chemoselectivity observed. the Partner Organisations 2014.

A new class of heterogeneous platinum catalysts for the chemoselective hydrogenation of nitroarenes

Pandarus, Valerica,Ciriminna, Rosaria,Beland, Francois,Pagliaro, Mario

scheme or table, p. 1306 - 1316 (2011/06/25)

A new series of nanostructured platinum catalysts able to catalyze the selective reduction of nitroarenes has been developed. The materials, made of organosilica physically doped with nanostructured platinum(0), are stable and efficient. Reactions in general proceed with high yield and often go to completion, while the catalysts can be reused in further reaction runs. This establishes a new class of relevant solid catalysts for synthetic organic chemistry named SiliaCat Platinum-Hydrogel.

Selective partial hydrogenation of dinitrobenzenes to nitroanilines catalyzed by Ru/C

Hou, Jie,Ma, Yonghuan,Li, Yuhan,Guo, Fang,Lu, Lianhai

scheme or table, p. 974 - 975 (2009/04/06)

Ru/C was found to be a highly effective catalyst for the selective partial hydrogenation of a range of dinitrobenzenes to their corresponding nitroanilines with excellent selectivity under mild conditions. Furthermore, the effect from other substitute groups of dinitrobenzenes on partial hydrogenation was also explored in this study. Copyright

One step hair coloring compositions using salts

-

, (2008/06/13)

A hair coloring composition comprising the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an amino phenol, a naphthol, a polyhydric phenol, a catechol and mixtures thereof; wherein the composition comprising one or more oxidative hair coloring agents further comprises al least one water soluble carbonate releasing salts; and optionally a water soluble ammonium salt, is described.

Transition metal complexes as dye forming catalysts in hair coloring compositions

-

, (2008/06/13)

A hair coloring composition comprising a first composition which comprises: (a) a dye forming transition metal salt or complex; which is first applied to the hair; and a second composition which comprises the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an aminophenol, a polyhydric phenol a catechol and mixtures thereof.

Unusual reaction of 1,4-diamino-2-nitrobenzene derivatives toward nucleophiles: Catalysis by sodium sulphite

Forlani, Luciano,Boga, Carla,Mazza, Milena,Cavrini, Vanni,Andrisano, Vincenza

, p. 4647 - 4654 (2007/10/03)

Unusual substitution of amino group occurs by reactions of some 1,4diamino-2-nitrobenzenes (semipermanent hair dyes) and nucleophiles (NH3, H2O). The reaction is catalyzed by sodium sulfite. The obtained products are suspected of being toxic substances which may be present in cosmetic matrices. Apparently, this reaction is a nucleophilic aromatic substitution but it may be explained by a mechanism involving a tautomeric form of substrate.

Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides

Monge, Antonio,Palop, Juan A.,Cerain, Adela Lopez de,Senador, Virginia,Martinez-Crespo, Francisko J.,et al.

, p. 1786 - 1792 (2007/10/02)

Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy.Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy.The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells.Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and /or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells.Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced.Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxide have reduction potentials significantly more positive than Tirapazamine (Epc -0.90 V).The most potent cytotoxins to cells in culture were the 6,7-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine.The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity.Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro.In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine.This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.

Hair dye preparations containing substantive nitrodiphenylamine derivatives

-

, (2008/06/13)

This invention encompasses compounds of the formula: STR1 wherein: one of R1 or R2 is nitro and the other is --SO3 H or COOH; and one of R3 or R4 is hydrogen and the other is --NR5 R6, where R5 and R6 independently are hydrogen, C1-4 alkyl, or C2-4 hydroxyalkyl; or a water soluble salt thereof; hair dye preparations containing the above compounds as substantive hair dyes; and methods for dyeing hair using such preparations.

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