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
• Article Data: 2

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.