140-50-1

Basic information

• Product Name: N,N'-DIACETYL-1,4-PHENYLENEDIAMINE
• Synonyms: N,N'-P-PHENYLENEBISACETAMIDE;N,N'-DIACETYLPHENYLENEDIAMINE;N',N-DIACETYL-P-PHENYLENEDIAMINE;N,N'-DIACETYL-1,4-PHENYLENEDIAMINE;N,N'-1,4-PHENYLENEBISACETAMIDE;N,N DIACETO 1:4 PHENYLENE DIAMINE;TIMTEC-BB SBB006302;1,4-Bisacetamidobenzene
• CAS NO: 140-50-1
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21
• EINECS: 205-417-3
• Mol File: 140-50-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: >300°C
• Boiling Point: 483.8 °C at 760 mmHg
• Flash Point: 219.6 °C
• Appearance: Dark yellow crystals
• Density: 1.235 g/cm³
• PKA: 14.29±0.70(Predicted)
• BRN: 2806271
• CAS DataBase Reference: N,N'-DIACETYL-1,4-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DIACETYL-1,4-PHENYLENEDIAMINE(140-50-1)
• EPA Substance Registry System: N,N'-DIACETYL-1,4-PHENYLENEDIAMINE(140-50-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2811
• RTECS: AC7709500
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 140-50-1(Hazardous Substances Data)

Usage

General Description

N,N'-Diacetyl-1,4-phenylenediamine is a chemical compound commonly used in hair dyes and colorants. It acts as a colorant by reacting with hydrogen peroxide to form larger, darker molecules that can adhere to the hair shaft. This chemical is also used in the production of permanent hair dyes, where it helps to create lasting color by penetrating the hair shaft and bonding with the natural pigments. However, N,N'-Diacetyl-1,4-phenylenediamine has been linked to allergic reactions and skin irritation in some individuals, leading to concerns about its safety in cosmetic products. Therefore, it is important to use this chemical with caution and in accordance with safety guidelines.

Upstream product

• 108-24-7 acetic anhydride 
• 16245-77-5 p-phenylenediammonium sulfate 
• 106-50-3 1,4-phenylenediamine 
• 2051-49-2 n-hexanoic anhydride 
• 27912-60-3 1,4-diacetylbenzene dioxime 
• 100-25-4 para-dinitrobenzene 
• 141-78-6 ethyl acetate 
• 100-01-6 4-nitro-aniline 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 75-05-8 acetonitrile 
• 105-53-3 diethyl malonate 
• 56072-03-8 1-(4-aminophenyl)ethanone oxime 
• 13483-16-4 2,4,6-triacetyloxy-1,3,5-triazine 
• 1212-62-0 1,4-bis-NN-(dimethylaminomethyleneamino)benzene 

Downstream Products

• 528572-74-9 (N-[4-(acetylamino)-η6-phenyl]acetamide)[1,1'-binaphthalene-2,2'-diylbis(diphenylphosphane)-κ2P,P']hydridoruthenium(II)trifluoromethanesulfonate 
• 528572-76-1 (N-[4-(N-acetylamino)-η6-phenyl]acetamide)[6,6'-dimethoxybiphenyl-2,2'-diylbis(diphenylphosphane)-κ2P,P']hydridoruthenium(II) trifluoromethanesulfonate 
• 25445-10-7 N,N'-Diacetyl-1,4-diamino-2,5-dibrombenzol 
• 1630-53-1 isoquinolino[3,4-b]phenanthridine 
• 36861-70-8 3,8-diphenyl-[4,7]phenanthroline 
• 102079-39-0 N,N-dimethyl-4-[4,7]phenanthrolin-3-yl-aniline 
• 101936-20-3 3-p-tolyl-4,7-phenanthroline 
• 93656-09-8 3-phenyl-[4,7]phenanthroline 
• 17788-94-2 4,4''-dibromo-p-terphenyl 
• 1762-84-1 4-bromo-p-terphenyl 
• 92-94-4 [1,1';4',1'']terphenyl 
• 50610-32-7 N,N'-(chloro-p-phenylene)-bis-acetamide 
• 6645-64-3 N,N’-dinitroso-p-phenylenediamine-N,N’-diacetic acid 
• 10097-07-1 N,N'-(1,4-phenylene)bis(glycine) 

Relevant articles and documents

Synthesis and Initiation Capabilities of Energetic Diazodinitrophenols

The diazophenols 3-amino-6-diazo-2, 4-dinitrophenol (4) and 3-chloro-6-diazo-2, 5-dinitrophenol (8) were synthesized and comprehensively characterized. The regio-selectivity of nitration reactions with N,N′-(1,4-phenylene)dimethanesulfonamide (1) and N,N′-(1,4-phenylene)diacetamide (6) was investigated in detail. The purity of the products was confirmed via low temperature X-ray diffraction, multinuclear NMR spectroscopy, and elemental analysis. Moreover, the capability of 4 and 8 to initiate RDX (1,3,5-trinitro-1,3,5-triazinane) was tested, together with the two other recently presented diazophenols 4-diazo-2, 6-dinitrophenol (iso-DDNP) and 3-hydroxy-DDNP (HODDNP). The tests revealed superior properties of HODDNP compared to DDNP and the other tested diazophenols regarding its ability to initiate RDX.

Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water

Developing and/or modifying fundamental chemical reactions using chemical industry-favorite heterogeneous recoverable catalytic systems in the water solvent is very important. In this paper, we developed convenient, green, and efficient approaches for the chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes in the presence of the recoverable heterogeneous carbon-supported palladium (Pd/C) catalytic system in water. The utilize of the simple, effective, and recoverable catalyst and also using of water as an entirely green solvent along with relatively short reaction times and good-to-excellent yields of the desired products are some of the noticeable features of the presented synthetic protocols. Graphic abstract: [Figure not available: see fulltext.].

Tin(ii) chloride dihydrate/choline chloride deep eutectic solvent: Redox properties in the fast synthesis of: N -arylacetamides and indolo(pyrrolo)[1,2- a] quinoxalines

In this contribution a physicochemical, IR and Raman characterization for the tin(ii) chloride dihydrate/choline chloride eutectic mixture is reported. The redox properties of this solvent were also studied by cyclic voltammetry finding that it can be successfully used as an electrochemical solvent for electrosynthesis and electroanalytical processes and does not require negative potentials as verified by the reduction of nitrobenzene. The potential use of this eutectic mixture as a redox solvent was further explored in obtaining aromatic amines and N-arylacetamides starting from a wide variety of nitroaromatic compounds. In addition, a fast synthetic strategy for the construction of a series of indolo(pyrrolo)[1,2-a]quinoxalines was developed by reacting 1-(2-nitrophenyl)-1H-indole(pyrrole) with aldehydes. This simple protocol offers a straightforward method for the construction of the target quinoxalines in short reaction times and high yields where the key step involves a tandem one-pot reductive cyclization-oxidation.

Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement

A metal-free and redox-neutral method for Beckmann rearrangement employing inexpensive and readily available SO2F2 gas is described. The reported transformation proceeds at ambient temperature and is compatible with a wide range of sterically and electronically diverse aromatic, heteroaromatic, aliphatic and lignin-like oximes providing amides in good to excellent yields. The reaction proceeds through the formation of an imidoyl fluoride intermediate that can also be used for the synthesis of amidines.