606-79-1

Basic information

• Product Name: 1,6-dinitronaphthalen-2-ol
• CAS NO: 606-79-1
• Molecular Formula: C₁₀H₆N₂O₅
• Molecular Weight: 234.165
• Mol File: 606-79-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 416.9°C at 760 mmHg
• Flash Point: 184°C
• Density: 1.607g/cm³
• Vapor Pressure: 1.52E-07mmHg at 25°C
• Refractive Index: 1.745
• CAS DataBase Reference: 1,6-dinitronaphthalen-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-dinitronaphthalen-2-ol(606-79-1)
• EPA Substance Registry System: 1,6-dinitronaphthalen-2-ol(606-79-1)

Safety Data

• Hazardous Substances Data: 606-79-1(Hazardous Substances Data)

Usage

Synonyms

1,6-dinitronaphthol

Physical state

Yellow crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Synthesis

Intermediate in the production of dyes and pigments

Application

Used for red and yellow colors in dyes and pigments

Potential use

Corrosion inhibitor for metal surfaces

Hazards

Harmful if swallowed, inhaled, or in contact with the skin

Safety concerns

May cause irritation to the respiratory tract and eyes

Upstream product

• 135-19-3 β-naphthol 
• 131-91-9 1-Nitroso-2-naphthol 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 7697-37-2 nitric acid 
• 6756-41-8 1-(4-methylphenylazo)naphthalen-2-ol 
• 64-19-7 acetic acid 
• 842-07-9 Sudan I 

Downstream Products

• 610-27-5 4-nitrophthalic acid 
• 77667-84-6 (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(1,6-dinitro-naphthalen-2-yloxy)-tetrahydro-pyran 
• 77667-85-7 (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(1,6-dinitro-naphthalen-2-yloxy)-tetrahydro-pyran 
• 67550-99-6 2-β-Carboxyvinyl-4-nitrophenylhydroxamsaeure 

Relevant articles and documents

Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation

The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.

Oxidation of 1-acyl-2-naphthol oximes: peri- and o-cyclisation and spiro cyclodimerisation of naphthoquinone nitrosomethide intermediates

The oxidation of 2-hydroxynaphthaldehyde oxime with lead(IV) acetate (LTA) gave a mixture of naphtho[1,8-de][1,2]oxazine and a spiro dimer. LTA oxidation of 6-bromo (or nitro)-2-hydroxynaphthaldehyde oximes provided only spiro dimers. Similar treatment of (2-hydroxy-1-naphthyl)keto oximes with LTA gave naphtho[1,8-de][1,2]oxazines and benzo[cd]indol-3(1H)-ones. Low temperature oxidation of 1-(2-hydroxy-1-naphthyl)propan-1-one oxime furnished 2-ethylbenzo[cd]indol-3(1H)-one and 1-ethylnaphtho[1,2-d]isoxazole-2-oxide. peri- and o-Naphthoquinone nitrosomethides are invoked as intermediates that undergo peri- and o-cyclisation and intermolecular cyclodimerisation.