776-34-1

Basic information

• Product Name: 4-Nitro-1-naphthylamine
• Synonyms: 08890_FLUKA;4-12-00-03114 (Beilstein Handbook Reference);A70003_ALDRICH;AI3-62662;BRN 2211897;EINECS 212-277-7;NSC 614;NSC614
• CAS NO: 776-34-1
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18
• EINECS: 212-277-7
• Product Categories: Amines;Fused Ring Systems
• Mol File: 776-34-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: 190-193 °C(lit.)
• Boiling Point: 419°C at 760 mmHg
• Flash Point: 207.2°C
• Appearance: /
• Density: 1.366g/cm³
• Vapor Pressure: 3.13E-07mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 1.31±0.10(Predicted)
• BRN: 2211897
• CAS DataBase Reference: 4-Nitro-1-naphthylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitro-1-naphthylamine(776-34-1)
• EPA Substance Registry System: 4-Nitro-1-naphthylamine(776-34-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: QM4370000
• Hazardous Substances Data: 776-34-1(Hazardous Substances Data)

Usage

Purification Methods

It crystallises from EtOH, ethyl acetate or aqueous NH3 as light yellow crystals. The acetyl derivative also forms yellow crystals, m 192.5-193.5o, from Me2CO. [Beilstein 12 H 1259, 12 I 530, 12 II 704, 12 III 2971, 12 IV 3114.]

InChI:InChI=1/C10H8N2O2/c11-9-5-6-10(12(13)14)8-4-2-1-3-7(8)9/h1-6H,11H2

Upstream product

• 605-61-8 1-chloro-4-nitronaphthalene 
• 605-62-9 4-nitro-1-naphthol 
• 86-57-7 1-Nitronaphthalene 
• 7803-49-8 hydroxylamine 
• 141-52-6 sodium ethanolate 
• 134-32-7 1-amino-naphthalene 
• 2801-21-0 benzothiazole sulfenamide 
• 865-47-4 potassium tert-butylate 
• 75358-95-1 pyridine-2-carboxylic acid naphthalen-1-ylamide 
• 6921-26-2 1,4-dinitronaphthalene 
• 91-20-3 naphthalene 
• 118535-52-7 N,N-tetramethylene-thiocarbamoyl-sulphenamide 
• 21660-76-4 2-(naphthalen-1-ylamino)-2-oxoacetic acid 
• 605-71-0 1,5-dinitronaphthalene 

Downstream Products

• 36942-38-8 N-(4-nitronaphthalen-1-yl)-4-benzenesulfonamide 
• 83733-42-0 (E)-1-(4-hydroxyphenylazo)-4-nitronaphthalene 
• 88-06-2 2,4,6-Trichlorophenol 
• 878672-00-5 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid 
• 321694-20-6 4-methoxy-N-[4-[(4-methoxyphenyl)sulfonylamino]-1-naphthyl]benzenesulfonamide 
• 34599-42-3 6-nitrobenzindol-2(1H)-one 
• 4684-12-2 1-amino-4-chloronaphthalene 

Relevant articles and documents

Synthesis and application of 2-(arylazo)-8-nitronaphtho[1,2-d] thiazole disperse dyes

The paper describes the synthesis of 2-amino-8-nitronaphtho[1,2-d]thiazole and its utilization to prepare a range of heterocyclic azo disperse dyes. These arylazo dyes were studied with respect to their color and constitution relationship. These dyes were applied on polyester fibre and their fastness properties were evaluated.

Keap1-Nrf2 PPI inhibitor prodrug and preparation method and application

The invention discloses a Keap1-Nrf2 PPI inhibitor prodrug and a preparation method and application. According to the prodrug P-168 provided by the invention, a polar carboxylic acid group of an active compound 168 is blocked, so that the fat solubility is improved, and the membrane permeability and druggability are effectively improved; the prodrug P-168 is reduced under the condition of high ROS, a pharmacophore 168 and a fluorophore coumarin are released, expression of Nrf2 and downstream genes of Nrf2 is activated, anti-inflammatory activity is brought into play, and meanwhile fluorescenceis released to achieve visual monitoring.

Unravelling the mechanism of cobalt-catalysed remote C-H nitration of 8-aminoquinolinamides and expansion of substrate scope towards 1-naphthylpicolinamide

Previously, an unexpected Co-catalysed remote C-H nitration of 8-aminoquinolinamide compounds was developed. This report provided a novel reactivity for Co which was assumed to proceed through the mechanistic pathway already known for analogous Cu-catalysed remote couplings of the same substrates. In order to shed light into this intriguing, and previously unobserved reactivity for Co, a thorough computational study has now been performed, which has allowed for a full understanding of the operative mechanism. This study demonstrates that the Co-catalysed remote coupling does not occur through the previously proposed Single Electron Transfer (SET) mechanism, but actually operates through a high-spin induced remote radical coupling mechanism, through a key intermediate with significant proportion of spin density at the 5- and 7-positions of the aminoquinoline ring. Additionally, new experimental data provides expansion of the synthetic utility of the original nitration procedure towards 1-naphthylpicolinamide which unexpectedly appears to operate via a subtly different mechanism despite having a similar chelate environment.

Sodium persulfate-promoted site-selective synthesis of mononitroarylamines under transition-metal-free conditions

A practical preparation of nitroarylamines from protected arylamines was herein disclosed. In this system, sodium nitrite acted as a nitration reagent in the presence of sodium persulfate without any transition-metal catalysts. This efficient site-selective protocol took place at room temperature for a short time through a free radical pathway.