2653-77-2

Basic information

• Product Name: 2-(PHENYLAZO)NAPHTHALENE
• Synonyms: 2-(PHENYLAZO)NAPHTHALENE
• CAS NO: 2653-77-2
• Molecular Formula: C₁₆H₁₂N₂
• Molecular Weight: 232.27988
• Mol File: 2653-77-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 394.8°Cat760mmHg
• Flash Point: 185°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 4.4E-06mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 2-(PHENYLAZO)NAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(PHENYLAZO)NAPHTHALENE(2653-77-2)
• EPA Substance Registry System: 2-(PHENYLAZO)NAPHTHALENE(2653-77-2)

Safety Data

• Hazardous Substances Data: 2653-77-2(Hazardous Substances Data)

Usage

Chemical composition

Consists of a naphthalene molecule with a phenylazo group attached to it.

Color

Characteristic orange-red color due to the presence of a nitrogen-nitrogen double bond.

Common uses

Used as a dye in the textile and food industries for products such as plastics, waxes, printing inks, and food coloring.

Health risks

Potential carcinogenic effects and ability to cause allergic reactions. Classified as a mutagen, meaning it can cause changes in DNA and lead to genetic mutations.

Safety precautions

Individuals should limit their exposure to 2-(phenylazo)naphthalene and use caution when handling products containing this compound. Banned in many countries.

InChI:InChI=1/C16H12N2/c1-2-8-15(9-3-1)17-18-16-11-10-13-6-4-5-7-14(13)12-16/h1-12H/b18-17+

Upstream product

• 91-59-8 naphthalen-2-ylamine 
• 7446-70-0 aluminium trichloride 
• 20893-80-5 naphthalene-2-diazonium chloride 
• 71-43-2 benzene 
• 581-97-5 2-acetylaminonaphthalene 
• 98-95-3 nitrobenzene 
• 112324-93-3 [1,4]benzoquinone-(N-[2]naphthyl oxime )-(N-phenyl oxime ) 
• 15057-55-3 N-sulfinyl-2-naphthylamine 
• 100-65-2 N-Phenylhydroxylamine 

Downstream Products

• 16914-55-9 2-NNO-Phenylazoxy-naphthalin 
• 94501-32-3 N-2-naphthyl-N'-phenylhydrazine 
• 93013-27-5 [1-(2-aminophenyl)naphthalen-2-yl]amine 
• 62-53-3 aniline 
• 91-59-8 naphthalen-2-ylamine 

Relevant articles and documents

Organocatalytic aryl-aryl bond formation: An atroposelective [3,3]-rearrangement approach to BINAM derivatives

Herein we disclose an organocatalytic aryl-aryl bond-forming process for the regio- and atroposelective synthesis of 2,2′-diamino-1,1′- binaphthalenes (BINAMs). In the presence of catalytic amounts of axially chiral phosphoric acids, achiral N,N′-binaphthyl hydrazines undergo a facile [3,3]-sigmatropic rearrangement to afford enantiomerically enriched BINAM derivatives in good to excellent yield. This transformation represents the first example of a metal-free, catalytic C(sp2)-C(sp2) bond formation between two aromatic rings with concomitant de novo atroposelective installation of an axis of chirality. Density functional calculations reveal that, in the transition state for C-C bond formation, the phosphoric acid proton of the catalyst is fully transferred to one of the N-atoms of the substrate, and the resulting phosphate acts as a chiral counterion.

Heavy-Atom Kinetic Isotope Effects in the Acid-Catalyzed Rearrangement of N-2-Naphtyl-N'-phenylhydrazine. Rearrangement Is Shown To Be a Concerted Process

Heavy-atom kinetic isotope effects (KIE) have been measured in the acid-catalyzed rearrangement of N-2-naphthyl-N'-phenylhydrazine (1) into 1-(o-aminophenyl)-2-naphthylamine (2).A combination of whole-molecule-ion and isotope ratio mass spectrometry and scintillation counting has given KIE for 15N, 13C, and 14C.Use of 1 and whole-molecule-ion mass spectrometry gave a KIE of 1.0434 (for two 15N atoms).Use of 1 and isotope-ratio mass spectrometry gave a KIE of 1.0196 for one naturally abundant 15N atom and 1.0042 for one 13C atom.Use of 1 gave a KIE of 1.0142 for one 14C atom.The results show that this rearrangement is a concerted process, namely a -sigmatropic shift.The transition state, furthermore, appears to be unsymmtetrical.That is, the extents of N-N bond breaking and C-C bond forming appear to be unequal.