6264-93-3

Basic information

• Product Name: 2-AMINO-2,4,6-CYCLOHEPTATRIEN-1-ONE
• Synonyms: 2-AMINO-2,4,6-CYCLOHEPTATRIEN-1-ONE;2-Aminotropone;2-amino-2,4,6-cycloheptarien-1-one;(2E,4Z,6Z)-2-aminocyclohepta-2,4,6-trienone
• CAS NO: 6264-93-3
• Molecular Formula: C₇H₇NO
• Molecular Weight: 121.13658
• Mol File: 6264-93-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 106.5°C
• Boiling Point: 225.84°C (rough estimate)
• Flash Point: 120.8°C
• Appearance: /
• Density: 1.1344 (rough estimate)
• Vapor Pressure: 0.00487mmHg at 25°C
• Refractive Index: 1.5323 (estimate)
• PKA: 2.25±0.20(Predicted)
• CAS DataBase Reference: 2-AMINO-2,4,6-CYCLOHEPTATRIEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-2,4,6-CYCLOHEPTATRIEN-1-ONE(6264-93-3)
• EPA Substance Registry System: 2-AMINO-2,4,6-CYCLOHEPTATRIEN-1-ONE(6264-93-3)

Safety Data

• Hazardous Substances Data: 6264-93-3(Hazardous Substances Data)

Usage

General Description

2-Amino-2,4,6-cycloheptatrien-1-one is a chemical compound with the molecular formula C7H7NO. It is a yellow to brown solid that is insoluble in water but soluble in organic solvents. 2-AMINO-2,4,6-CYCLOHEPTATRIEN-1-ONE is commonly used in organic synthesis and chemical research as a starting material for the synthesis of various nitrogen-containing compounds. It is also used as a ligand in coordination chemistry and as a building block for the preparation of pharmaceuticals and agrochemicals. Additionally, 2-amino-2,4,6-cycloheptatrien-1-one has potential applications in the development of dyes, pigments, and other specialty chemicals due to its unique chemical structure and reactivity.

InChI:InChI=1/C7H7NO/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H2,8,9)

Upstream product

• 64-17-5 ethanol 
• 225112-68-5 2H-cycloheptaoxazol-2-one 
• 1153-05-5 triphenylarsineoxide 
• 53526-99-1 2-<2-(2-methoxyphenyl)hydrazino>tropone 

Downstream Products

• 225112-81-2 N-phenyl-N'-(tropon-2-yl)urea 
• 225112-61-8 2-(triphenylphosphoranylideneamino)tropone 
• 374685-67-3 (7-oxocyclohepta-1,3,5-trienylimino)triphenylarsorane 
• 65425-79-8 [(2-oxo-3,5,7-cycloheptatrien-1-yl)amino]oxo-acetic acid 
• 65425-48-1 [(2-oxo-3,5,7-cycloheptatrien-1-yl)amino]oxo-acetic acid ethyl ester 
• 374685-69-5 C₇H₅ONSb(C₆H₅)3 
• 345259-39-4 (tropon-2-yl)-N=BiPh₃ 
• 603-36-1 triphenylantimony 
• 603-33-8 triphenylbismuthane 
• 22704-53-6 3-iodo-tropolone 
• 25946-69-4 1-thia-3-azaazulene-2(1H)-one 
• 3481-50-3 1-phenylcycloheptaimidazole-2(1H)-one 

Relevant articles and documents

Synthesis, structure, and reactivity of (tropon-2-ylimino)arsorane and in situ generation of its stiborane and bismuthorane analogues: Reactions with heterocumulenes and an activated acetylene giving heteroazulenes

(Tropon-2-ylimino)pnictoranes of the general structure RN=MPh3 (R = tropon-2-yl; M = As, Sb, and Bi) 4-6 have been prepared for the first time by the reaction of 2-aminotropone with Ph3MX2 (M = As, Sb, and Bi) in the presence of a base. The arsorane derivative (M = As) 4 is isolated as a stable crystalline compound, while the stiborane (M = Sb) and the bismuthorane (M = Bi) derivatives 5 and 6 are not isolated and are prepared in situ due to their moisture sensitivity. The X-ray crystal analysis revealed that compound 4 exhibits two different conformations in the solid state, and that the As-O bond distances (2.33 A) lie below the sum of the van der Waals radii (3.37 A), and thus, there is appreciable bonding interaction between the arsine and the oxygen atoms. With a view to constructing a series of cyclohepta-annulated heterocycles and in order to gain a better understanding of a series of iminopnictoranes, compounds 4-6 were allowed to react with heterocumulenes such as carbon disulfide, phenyl isothiocyanate, phenyl isocyanate, and diphenylcarbodiimide, in an aza-Wittig/electrocyclization or a formal [8 + 2] type cycloaddition eliminating triphenylpnictorane oxide to give 2H-cycloheptaoxazol-2-one, its thione, and imine derivatives. On the other hand, the reaction of compounds 4 and 5 with dimethyl acetylenedicarboxylate (DMAD) gives postulated dimethyl cyclohepta[b]pyrrole-2,3-dicarboxylate, which subsequently reacts with DMAD to result in the formation of tetramethyl 2H-cyclohepta[gh]pyrrolizine-1,2,4,5-tetracarboxylate, while the reaction of 6 gives only intractable tarry materials. The reactivity of the compounds 4-6, which contain a formal N=M (M = As, Sb, and Bi) double bond, has been clarified to be in the order of 6 (M = Bi) > 5 (M = Sb) > 4 (M = As) > [the corresponding iminophosphorane derivative 3 (M = P)].

Synthesis and Reactions of 2-Arylhydrazinotropones. II. Synthesis of 5-Aryltropolones and B-Ring-Open Colchicine Analogues via Benzidine Type Rearrangement of 2-(2-Arylhydrazino)tropones

Treatment of a wide variety of 2-(2-arylhydrazino)tropones with ethanolic acid at 50-80 deg C readily gave the benzidine type rearrangement products, 2-amino-5-(4-aminoaryl)tropones, besides minor amounts of byproducts of various type.The main products were conveniently led to the corresponding 5-aryltropolones.Similarly, 2-(2-arylhydrazino)tropones bearing an isopropyl and isopropenyl group at the 4-position afforded 4-substituted 2-amino-5-(4-aminoaryl)tropones as the main products, which were also led to 4-substituted 5-(4-acetamidoaryl)- and 5-(4-methoxyaryl)tropolones.Structural assignments of these products were made on the basis of 1H NMR and other spectral data as well as of chemical transformations to known 5-phenyltropolone and also to 2-acetamido-8-hydroxy-10,10-dimethylcycloheptinden-7(10H)-one.This synthetic scheme may possibly be utilized for a convenient synthesis of B-ring-open analogues of colchicine.