4569-83-9

Basic information

• Product Name: 4-MORPHOLINO-1,2-NAPHTHOQUINONE
• Synonyms: 4-MORPHOLINO-1,2-NAPHTHOQUINONE;4-Morpholino-1,2-naphthalenedione
• CAS NO: 4569-83-9
• Molecular Formula: C₁₄H₁₃NO₃
• Molecular Weight: 243.25792
• Mol File: 4569-83-9.mol

Chemical Properties

• Boiling Point: 422.5°Cat760mmHg
• Flash Point: 209.3°C
• Appearance: /
• Density: 1.331g/cm³
• Vapor Pressure: 2.4E-07mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 4-MORPHOLINO-1,2-NAPHTHOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-MORPHOLINO-1,2-NAPHTHOQUINONE(4569-83-9)
• EPA Substance Registry System: 4-MORPHOLINO-1,2-NAPHTHOQUINONE(4569-83-9)

Safety Data

• Hazardous Substances Data: 4569-83-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H13NO3/c16-13-9-12(15-5-7-18-8-6-15)10-3-1-2-4-11(10)14(13)17/h1-4,9H,5-8H2

Upstream product

• 110-91-8 morpholine 
• 521-24-4 sodium 1,2-naphthoquinone-4-sulfonate 

Downstream Products

• 108731-54-0 4-(Benzo[f]quinoxalin-6-ylamino)-2-diethylaminomethyl-phenol; compound with sulfuric acid 
• 108731-42-6 4-(4-Hydroxy-3-diethylaminomethylphenyl)amino-1,2-naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 

Relevant articles and documents

Reaction of 1,2-naphthoquinone-4-sulfonate with aliphatic amines: Structure of the colored products and kinetics

Substitution of the 4-sulfonate in sodium 1,2-naphthoquinone-4-sulfonate (I) with many kinds of aliphatic amines (II) yields colored 4-substituted 1,2-naphthoquinones (Q): 4-morpholino-Q (IIIa), 4-piperidino-Q (IIIb), 4-pyrrolidino-Q (IIIc), 4-(1,2,4-triazol-1-yl)-Q (IIId), 4-(2-pyrrolyl)-Q (IIIe), 4-dimethylamino-Q (IIIf), 4-diethylamino-Q (IIIg), 4-isopropylamino-Q (IIIh), and 4-(4-amino-2-methyl-5-pyrimidylmethylamino)-Q (IIIi). The eliminated sulfite adds rapidly to the 4-position in I to form a colorless by-product, disodium 2-hydroxy-1-oxo-1,4-dihydro-4,4-naphthalenedisulfonate (IV). The rates of reactions were measured by polarography. The formations of IIIa and IV are successive second-order reactions. The pH profile of the rate constant, with a rounded peak at pH 10, suggests nucleophilic substitution of the free base (II) at the 4-carbon in the o-quinone form (I). The hydrolysis of IIIa to 2-hydroxy-1,4-naphthoquinone (V) is an acid-base-catalyzed pseudo-first-order reaction. The best conditions for photometric determination of morpholine (IIa) were found to be reaction of IIa with excess I at pH 8 and 25°C for 30 min.

Photochromic naphthopyran compounds

Described are novel reversible photochromic naphthopyran compounds, examples of which are compounds substituted at the 3 position of the pyran ring with (i) an aryl substituent and (ii) a phenyl substituent having a 5- or 6-member heterocyclic ring fused at the number 3 and 4 carbon atoms of the phenyl substituent, and at the 6 position of the naphthyl portion of the naphthopyran compound with a nitrogen-containing heterocyclic ring. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.