6086-29-9

Basic information

• Product Name: 1-N-ACETYL-3-NITRO-P-PHENYLENEDIAMINE
• Synonyms: 4-AMINO-3-NITROACETANILINE;1-N-ACETYL-3-NITRO-P-PHENYLENEDIAMINE;N-(4-amino-3-nitrophenyl)acetamide;Acetamide, N-(4-amino-3-nitrophenyl)-;Einecs 228-019-1;4'-Amino-3'-nitroacetanilide;N-(4-Amino-3-nitrophenyl)acetamide, 4-(Acetylamino)-2-nitroaniline, 4-Acetamido-2-nitroaniline, N1-Acetyl-3-nitrobenzene-1,4-diamine;N-(4-Amino-3-nitrophenyl)acetamide, 4-Acetamido-2-nitroaniline
• CAS NO: 6086-29-9
• Molecular Formula: C₈H₉N₃O₃
• Molecular Weight: 195.18
• EINECS: 228-019-1
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 6086-29-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 211.5-212.0 °C
• Boiling Point: 332.7°C at 760 mmHg
• Flash Point: 155°C
• Appearance: /
• Density: 1.428g/cm³
• Vapor Pressure: 0.000143mmHg at 25°C
• Refractive Index: 1.674
• PKA: 13.83±0.70(Predicted)
• CAS DataBase Reference: 1-N-ACETYL-3-NITRO-P-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-N-ACETYL-3-NITRO-P-PHENYLENEDIAMINE(6086-29-9)
• EPA Substance Registry System: 1-N-ACETYL-3-NITRO-P-PHENYLENEDIAMINE(6086-29-9)

Safety Data

• Hazardous Substances Data: 6086-29-9(Hazardous Substances Data)

Usage

Chemical classification

1-N-Acetyl-3-nitro-p-phenylenediamine is an aromatic amine.

Functional groups

Contains both an acetyl group and a nitro group.

Common uses

Intermediate in the production of dyes and pigments, hair dyes, and cosmetics.

Color

Yellow to orange.

Hair dye application

Often used in the formulation of permanent hair dyes, as well as some temporary and semi-permanent hair color products.

Allergic reactions

Associated with allergic reactions and skin sensitization in some individuals.

Regulatory status

Use is regulated in some countries.

Safety precautions

Important to use with caution and follow safety guidelines.

InChI:InChI=1/C8H9N3O3/c1-5(12)10-6-2-3-7(9)8(4-6)11(13)14/h2-4H,9H2,1H3,(H,10,12)

Upstream product

• 5307-14-2 2-nitro-1,4-phenylenediamine 
• 108-24-7 acetic anhydride 
• 860765-87-3 N-(4-acetylamino-2-nitro-phenyl)-phthalimide 
• 7664-41-7 ammonia 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 106-50-3 1,4-phenylenediamine 
• 476321-12-7 (4-acetylamino-phenyl)-oxalamic acid 
• 103-92-4 4'-aminoxanilic acid 
• 69066-56-4 Ethyl 4-acetylaminooxanilate 
• 140-50-1 N,N'-diacetyl-1,4-phenylenediamine 
• 7732-18-5 water 
• 860766-17-2 N-(4-acetylamino-2-nitro-phenyl)-phthalamic acid 
• 5345-53-9 nitro-p-phenylenediamine N¹,N⁴-diacetate 
• 64-19-7 acetic acid 

Downstream Products

• 100383-41-3 1,2-diamino-4-acetamidobenzene dihydrochloride 
• 25826-33-9 1,2,4-triaminobenzene N¹,N⁴-diacetate 
• 5345-53-9 nitro-p-phenylenediamine N¹,N⁴-diacetate 
• 27908-96-9 benzoic acid-(4-amino-3-nitro-anilide) 
• 5307-14-2 2-nitro-1,4-phenylenediamine 
• 6086-30-2 N-(4-azido-3-nitro-phenyl)-acetamide 
• 117131-13-2 4-acetamido-N-cyanomethyl-2-nitroaniline 
• 35266-22-9 C₁₁H₁₂N₄O₅S 
• 35266-16-1 C₁₂H₁₄N₄O₅S 
• 20809-93-2 4-acetylamino-2-nitro-benzenediazonium; chloride 
• 861801-17-4 4-acetylamino-2-nitro-benzenediazonium-betaine 

Relevant articles and documents

Regioselective N-acetylation as a route of nitro-p-phenylenediamine metabolism by rat liver cytosol

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INDOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS

The present invention relates to new indole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole compounds as an active ingredient.

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

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.